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Apartments and Condos in Longboat Key, FL

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    All 71 Rentals in Longboat Key
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    Travelers to Longboat Key are booking January dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 7
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    $791
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    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
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    $171
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Stereo System
    • Ocean Views
    • Satellite TV
    • Water Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Doctor's hidden home with gorgeous views: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. Wi-Fi & Cable TV Our Venetian / Mediterranean Villa is nestled on the placid Longboat Key. With a short drive... View all property information
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    Longboat Key, Florida 34228
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    $99
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    Studio / 1 Bathroom / Sleeps 3
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    • Water Views
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Private Outdoor...
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    The Beach on Longboat Key - New Gulf Front Condo # 103 *** Beach Front Special ~ From $99/night *** July 8 -10 , July 12 - 15 July 19 - 21 , July 25 - 29 , Aug 2 - 7 This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach... View all property information
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    Longboat Key, Florida 34228
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    $2,250
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    1 / 29
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Water Views
    • Watersports Nearby
    • Air Conditioning
    • Ocean Views
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Waterfront
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • x
    About this property
    Nestled among majestic palms and tropical landscaping, this Country Club Shores home also available VRBO #704978 is situated on a deep sailboat water canal with 113 feet of waterfront, and offers outstanding boating opportunities - all just two blocks away from Sarasota Bay! Southern exposure on... View all property information
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    Longboat Key, Florida 34228
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    $200
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    1 / 5
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Shared Outdoor Pool...
    • Water Views
    • Stereo System
    • Internet Access
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This spectacular two bedroom condominium sits directly fronting on the Gulf in the middle of Long Boat Key. It was recently renovated from floor to ceiling and is beautifully decorated with warm, rich colors. The kitchen has stainless appliances, granite countertops and custom dark polished wood... View all property information
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    Longboat Key, Florida 34228
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    $199
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    1 / 15
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Watersports Nearby
    • Water Views
    • Shared Tennis Court
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Groundfloor Beachfront! From large living and dining area with open kitchen just step outside to your patio with privacy and walk right out to the BEACH! Magnificent condo with open floor plan, very comfortable for 4 people. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen, recliner sofa,... View all property information
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    Longboat Key, Florida 34228
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    $179
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    1 / 30
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Shared Tennis Court
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our condo has everything you will need for a relaxing vacation on the beach. The island of Longboat Key... ... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine.... View all property information
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    Location Information
    Longboat Key, Florida 4725
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    $129
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    1 / 23
    1 Bedroom / 1 Bathroom / Sleeps 3
    travelers have booked this property
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    • Internet Access
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Water Views
    • Washer
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    *** SPECIAL From $125 per night *** August and September The Beach on Longboat Key - New 1 Bedroom Gulf Front Condo # 225 This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. A heated... View all property information
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    Location Information
    Longboat Key, Florida 34231
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    $193
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    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Sauna
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Water Views
    • Hot Tub
    • Satellite TV
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    !!!!SUMMER SPECIAL!!!! JULY & AUGUST 2015 - ONLY 1,000 USD/WEEK OR 1,750 USD FOR 2 WEEKS Feel at home in this spacious waterfront condominium on Longboat Key with luxurious amenities, including heated pool and hot tub with views of the Sarasota Bay, tropical gardens, private boat dock and four... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 9, 2015
    All 'first" for us. First time on Longboat Key, first time at spring training and first time using Tripadvisor/Flipkey. And the property - first rate : ). The location was great...
    5 of 5 stars Reviewed October 15, 2014
    The condo was spotless and well equipped with all of our vacation needs. The rooms are spacious and the view is stunning. We will never stay anywhere else when we go to Florida...
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    $120
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveler have booked this property
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    • Satellite TV
    • Private Fishing...
    • Air Conditioning
    • Shared Tennis Court
    • Watersports Nearby
    • Internet Access
    • Waterfront
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile... View all property information
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    Longboat Key, Florida 34228
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    $195
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    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Dryer
    • Satellite TV
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Water Views
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the... View all property information
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    Longboat Key, Florida 34228
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    $269
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • DVD Player
    • Stereo System
    • Washer
    • Waterfront
    • Satellite TV
    • Water Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Florida's SeaHorse Beach Resort on Longboat Key is located on the white sand beaches of the Gulf of Mexico. From the moment you arrive, the friendly and professional staff will welcome you to this Premier property where you can experience a panoramic view of the Gulf from your suite, or while... View all property information
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    Longboat Key, Florida 34228
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    $1,500
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    1 / 40
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Watersports Nearby
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • There Are Tennis...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Three bedroom cottage available weekly or monthly in the sought after North Longboat Key Village where resident peacocks visit daily. New beds, Linens, towels etc. Also available on VRBO #702686 Offered fully equipped unit reflecting its own unique style of a beach getaway in paradise, full of... View all property information
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    Longboat Key, Florida 34228
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    $190
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Washer
    • Water Views
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
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    Longboat Key, Florida 34228
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    $1,100
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    1 / 21
    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Satellite TV
    • Patio
    • Water Views
    • Internet Access
    • Waterfront
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This one-bedroom, ground floor walk-out, has fantastic full gulf views and is only steps to the beach. It features a bright beach decor that will make your vacation in paradise truly memorable. The screened lanai is practically perched upon the sand! An added bonus is that it is a corner unit... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed November 27, 2014
    Very clean appartment, well equipped kitchen for self catering, with all the kitchen utensils spotlessly clean, very good position on the beach. Quite and very peaceful. Would go...
    5 of 5 stars Reviewed June 13, 2014
    I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
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    $3,500
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    1 / 18
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Shared Tennis Court
    • Air Conditioning
    • Stereo System
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This updated, 2 bedroom and 2 bath condo has sweeping views of the Gulf of Mexico with spectacular sunsets and a quiet beach that stretches for miles. At the north end of Longboat Key, there are plenty of restaurants, shopping and cultural activities nearby. Other amenities include a heated pool,... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $250
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    1 / 6
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Water Views
    • DVD Player
    • Satellite TV
    • Waterfront
    • Washer
    • Air Conditioning
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front... View all property information
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    Longboat Key, Florida 34228
    From
    $148
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    1 / 9
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Patio
    • Stereo System
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful 2 bedroom condo for rent by owner on Sand Cay beach. Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. Please read our reviews, you won't be dissapointed! The condo is unit 208 at the... View all property information
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    Longboat Key, Florida 34228
    4 of 5 stars Reviewed June 29, 2015
    I had to go to a work-related meeting in nearby Parrish, FL so I decided to rent a beach condo for a few days in order to mix work with leisure. I was traveling with my spouse...
    5 of 5 stars Reviewed May 2, 2014
    We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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    $214
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Internet Access
    • Stereo System
    • Air Conditioning
    • DVD Player
    • TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets View all property information
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    Longboat Key, Florida 34228
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    $5,500
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 5
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    Amenities & Details
    • Children's Pool
    • Shared Tennis Court
    • Wi-Fi
    • Waterfront
    • Sauna
    • Staffed Property
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 MONTH MINIMUM Elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool. Stunning mirrored and... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed November 21, 2014
    This is a beautiful condo with lovely furnishings and every resort amenity one could ask for. Lots of walk in closets, flat screens, Jacuzzi tub, large rooms and great views...
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
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    • Waterfront
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Watersports Nearby
    • Water Views
    • Game Room
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. Fully furnished kitchen, washer and dryer (in unit), dedicated parking for 1 car directly in front of unit, with additional guest parking. Master Bedroom has a king sized bed, flat screen TV, en... View all property information
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    Longboat Key, Florida 34228
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    $602
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
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    Longboat Key, Florida 34228
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    $1,400
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Children's Pool
    • Ping Pong Table
    • Water Views
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Million Dollar unobstructed ocean views. Right on the beach. Top floor. About a mile north from St Armand Circle. The condo has 2 bedrooms and 2 baths. Kitchen has granite and the place has everything you need. Just bring your clothes and food. Beautiful patio to enjoy the sunset views. Wi-Fi... View all property information
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    Longboat Key, Florida 34228
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    $167
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    1 / 41
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Water Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Stereo System
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
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    Longboat Key, Florida 34228
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    $1,400
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Private Outdoor...
    • Private Fishing...
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • DVD Player
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
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    Longboat Key, Florida 34228
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    $142
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Satellite TV
    • DVD Player
    • Stereo System
    • Patio
    • Dryer
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $110
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    1 / 29
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Water Views
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Stereo System
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    WINDWARD BAY CLUB on beautiful LONGBOAT KEY. This warm and inviting large 2 bedroom 2 bath corner unit is almost paradise. Meticulously furnished with all the comforts of home. Light and bright, with a view of the bay and the Mangroves from the large and roomy lanai. A short walk to the lovely... View all property information
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    Location Information
    Longboat Key, Florida 34228
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    $120
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Boat Available
    • Deck
    • TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This quiet 1 bedroom cozy stone cottage is nestled on the North end of Exclusive Longboat key. Sister Island to Anna Maria Island. A natural wild life preserve. Peacocks roam the streets, Sea turtles nest, Dolphins frolic and parrots fly freely, in this tropical paradise. Shopping, sight seeing... View all property information
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    Longboat Key, Florida 34228
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    $200
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Satellite TV
    • Washer
    • Stereo System
    • DVD Player
    • Waterfront
    • Water Views
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    We have a two bedroom, comfortably furnished condo unit overlooking the Gulf of Mexico. Our favorite room is the lanai - a screened in porch area with dining table and sitting area, especially the views as the sun sets over the Gulf. We are located on the north end of Longboat Key - more secluded... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed August 13, 2014
    This place is AWESOME, we stayed in the 4 bedroom housebayview with the private pool. It was the perfect vacation. The only mishap was the AC in one of the small rooms stopped...
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    $2,000
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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Shared Tennis Court
    • Private Fishing...
    • Staffed Property
    • Wi-Fi
    • Ping Pong Table
    • Game Room
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located in a beach to bay resort absolutely beautifully landscaped with a private beach, large pool, tennis courts, fishing pier on the bay and many more wonderful assets. This ground level condo with no 2nd level has its own outdoor patio making it very private. Renovated in June 2015 this condo... View all property information
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    Longboat Key, Florida 34228
    From
    $335
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Parking
    • Towels Provided
    • Private Outdoor...
    • Private Yard
    • Ocean Views
    • Air Conditioning
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Nestled among majestic palms and tropical landscaping, this Country Club Shores home is situated on a deep sailboat water with 113 feet of waterfront, and offers outstanding boating opportunities - all just two houses away from Sarasota Bay! Southern exposure on the canal side provides year-round... View all property information
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    Longboat Key, Florida 34228
    From
    $175
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    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Watersports Nearby
    • Waterfront
    • Ocean Views
    • There Are Tennis...
    • Air Conditioning
    • TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming 1 bedroom 1 bath canal front unit. On canal with dock in the Back yard. A beautiful Beach, amazing 35 acre park, great restaurants All within a five minute walk. Great space in an amazing place! Everything you Need to relax for a long weekend, a week, a month, or a winter, or summer... View all property information
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    Longboat Key, Florida 34228
    From
    $850
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    1 / 29
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Patio
    • Satellite TV
    • Refrigerator
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom one bath very affordable cottages are available weekly or monthly in the eclectic Longbeach Village where resident peacocks visit daily. New Beds, Linens, Towels etc.. Also available on VRBO #706230 Offered FULLY FURNISHED with each unit reflecting its own style of a beach getaway... View all property information
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    Longboat Key, Florida 34228
    From
    $128
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    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Linens Provided
    • Private Yard
    • Grill
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom one bath cottage all new beds, Linens, towels etc. Cottage available weekly or monthly in the Lovely North Longboat Key Village where resident peacocks visit daily. Sit out on your porch in the evening and relax or dine out at many of the water front restaurants. Offered FULLY... View all property information
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    Longboat Key, Florida 34228
    From
    $159
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    1 / 14
    5 of 5 stars (6) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (6) Make Inquiry
    Amenities & Details
    • Water Views
    • DVD Player
    • Refrigerator
    • Waterfront
    • Balcony
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS On beautiful tropically landscaped Longboat Key, Florida you will find the natural beauty. Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position. ENJOY THE... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed August 9, 2014
    Everything was perfect for 2 people. Nice decor, room set-up and proximity to beach. Quiet, mostly private feel (except for renovations being done next door). easy to arrange the...
    5 of 5 stars Reviewed July 21, 2014
    My husband and I enjoyed everything about our stay in this beautiful condo. Not only did we have a nicely decorated room inside, but our view was amazing outside. We were able to...
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    $2,303
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    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Private Outdoor...
    • Refrigerator
    • Dryer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the beautiful turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Rate... View all property information
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    Longboat Key, Florida 34228
    From
    $189
    / Night
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    1 / 26
    5 of 5 stars (4) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Staffed Property
    • Internet Access
    • Ocean Views
    • Water Views
    • Waterfront
    • Air Conditioning
    • Housekeeping...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. View all property information
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    Location Information
    Longboat Key, Florida 33312
    5 of 5 stars Reviewed July 2, 2014
    My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at...
    4 of 5 stars Reviewed May 6, 2014
    Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
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    From
    $204
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    1 / 39
    5 of 5 stars (5) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Washer
    • Satellite TV
    • Stereo System
    • DVD Player
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    At our beautiful low-rise resort, located directly on the beach, our two-bedroom condominium is fifty paces from the pool and a private beach of soft white sand. 15F in popular Casa del Mar provides a spacious living room/home theatre (46 inch plasma TV & BlueRay Player), vaulted ceilings, and a... View all property information
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    Longboat Key, Florida 34228
    4 of 5 stars Reviewed March 19, 2015
    Casa Del Mar is located in a beautiful part of Long Boat Key. The beach is beautiful and F15 condo was only steps away from the beach. There were plenty of lounge chairs on the...
    5 of 5 stars Reviewed July 4, 2014
    This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a brand...
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    $195
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    1 / 13
    4.5 of 5 stars (21) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (21) Make Inquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Water Views
    • Watersports Nearby
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    July 18-25 and Aug 8-15 are the earliest availability ++++++Rated ' EXCELLENT' digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence.... View all property information
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    Longboat Key, Florida 34228
    4 of 5 stars Reviewed June 11, 2015
    Seven of us stayed here...a combination of family and friends. It was great...well-equiped kitchen , extra pillows, large living area, washer & dryer, etc. Location was great...
    5 of 5 stars Reviewed February 26, 2015
    Our two families of 8 people total enjoyed our stay at Castle in the sky very much. The house is large but very comfortable. The weather in January can be fickle so one day the...
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    $225
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    4.5 of 5 stars (15) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (15) Make Inquiry
    Amenities & Details
    • DVD Player
    • Water Views
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    La Playa is a small 21-unit resort property of privately-owned condominiums available exclusively for weekly rentals twelve-months per year. Located on spectacular Longboat Key, a short drive from Sarasota on the wide sand beaches of the Gulf of Mexico, La Playa offers privacy and direct beach... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed June 18, 2015
    LaPlaya Condos are located literally on the beach. The condos are very clean and were perfectly suited for 2 adults and 2 teenagers. This area is not over crowded. Great...
    5 of 5 stars Reviewed April 23, 2015
    We have been coming down to Longboat Key from Chicago for several years now, staying at "our" unit at La Playa. Every year is always a great experience. The best part is simply...
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    $137
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    1 / 52
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Waterfront
    • Sauna
    • Air Conditioning
    • Shared Tennis Court
    • Children's Pool
    • Staffed Property
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    DEAL - $3500/42 Nights 10/21-12/1 + tax & fees from listing Booked until 7/31. For minimum bookings & rates scroll down to bottom here. PACK YOUR SWIMSUIT & SMILE - THE REST IS HERE: Take the wooden walkway to swim in warm gentle azure gulf waters Walk softly past sea turtle nests & shell... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 14, 2015
    The two balconies and lanai overlooking the fabulous Gulf of Mexico provide a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably...
    5 of 5 stars Reviewed November 29, 2014
    Club Longboat is a wonderful development with excellent property managers. I stayed at Ed's condo from August thru October of 2014. Even during the 'low season', this area is just...
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    $400
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    1 / 1
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our luxury vacation home will comfortably accomodate up to 12 guests and is located on a deepwater canal and has a dock suitable for a boat up to 30 feet in length. Beautiful Longboat Key beach is less than a 10 minute walk from the house and world-class shopping and dining at the famous St.... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $110
    / Night
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    1 / 10
    5 of 5 stars (13) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (13) Make Inquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Stereo System
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Housekeeping...
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    ****Please go to www.longboatbeach.com .**** for more information. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best view in the building A large shopping plaza, Avenue of the Flowers, is behind the complex, offering... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 17, 2015
    Very nice condo!! Clean and has everything you would need for a comfortable stay. Fantastic access to the beach. Beautiful and clean beach. Love that the beach is not crowded at...
    5 of 5 stars Reviewed October 15, 2014
    This condo had everything a person would want for a week or longer stay. The condo was clean and well decorated. My boyfriend and I enjoyed sitting on the balcony watching the...
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    $350
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    4.5 of 5 stars (11) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Deck
    • Water Views
    • DVD Player
    • Satellite TV
    • Waterfront
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Escape to Paradise with Incredible Sunsets and Balmy Breezes direct on the Gulf of Mexico with its beautiful White Sand Beaches stretching for miles. Private and very quiet, and features two bedrooms with a king size bed in the master suite and a queen size bed in the second bedroom, two full... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed July 3, 2014
    The location and view from the condo was outstanding. The condo came equipped with everything we needed. Easy access to gulf from back porch. Publix was close by to pick up a few...
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    $169
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    1 / 20
    4 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Waterfront
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our gulf front condominium has a beautiful view of the Gulf of Mexico not only from the balcony, but from the living room as well. We also have two other condos in this same resort that rent at lesser rates than shown below. We only recently purchased this condo, but in 2013 we replaced all the... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed May 19, 2015
    I was celebrating my 30th wedding anniversary. I could not of picked a better place. The rental was super clean had everything you can imagine there for use. I will definitely...
    5 of 5 stars Reviewed October 23, 2014
    This place was very clean and updated. The extra amenities such as the cooler's and ice packs was a huge plus. We had plenty of bedding, and towels and bathroom stuff. It’s not a...
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    $2,100
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    1 / 21
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Staffed Property
    • Shared Tennis Court
    • Ping Pong Table
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    • TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment. • Very private and quiet first floor, 1600 ft. unit with lush garden views. • Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom. • Guest bedroom with... View all property information
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    Longboat Key, Florida 34228
    From
    $1,750
    / Week
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    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Hot Tub
    • Water Views
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Large Gated Home on waterway - White Sand Beach only steps away. Our vacation home is spacious and beautifully furnished with 3 bedrooms and a large loft with sleeper-sofa, 3 full bathrooms, sleeps uo to 8 people, Perfect for families or couples. The home has a fully equipped gourmet kitchen with... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed May 28, 2015
    We stayed here from may 9 to 16 with my 2 kids (3.5 and 2 years old), husband and my parents. The house was more than we could ask for. Plenty of room, very nicely decorated...
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    $868
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    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Water Views
    • Waterfront
    • Private Fishing...
    • Watersports Nearby
    • Air Conditioning
    • Internet Access
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 24, 2015
    Lovely, well appointed, spotlessly clean beach house with tasteful decor and everything to make our stay comfortable and relaxed. Everything tastefully and thoughtfully done...
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    Beachfront condos and bayside villas – your vacation rental on Longboat Key

    Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.

    Longboat Key - the upscale coastal vacation destination

    This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

    Cultural treasures along Sarasota Bay

    Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

    Waterfront dining

    Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

    Visitor reviews aid vacation rental selection

    You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.