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Apartments and Condos in Longboat Key, FL

About Longboat Key
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    All 77 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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    $143
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    1 / 7
    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    $193
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    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    $735
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    1 / 7
    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
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    1 / 18
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    AwayToParadise com Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every... View all property information
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    5 of 5 stars Reviewed January 6, 2015
    The beach or the pool, it's all steps from the door. The place is well organized, clean, and beautiful. All basic necessities are there. Really enjoyable stay.
    5 of 5 stars Reviewed September 18, 2014
    My wife and I just came back from our best vacation ever! We have been to a lot of places in our life, but the Longboat Key is our #1 preference, it is heaven on earth! We loved...
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    $805
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    1 / 6
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Fishing...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    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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    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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    1 / 8
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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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    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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    $924
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    1 / 7
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our... View all property information
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    5 of 5 stars Reviewed December 10, 2014
    The owners were great, the place safe,clean,equipped,location perfect for walking to dine, shop and enjoy Longboat Key! We will be back!
    5 of 5 stars Reviewed September 28, 2014
    Don't let the word "Motel" detour you from checking out this fantastic property! There are 4 beautiful units right on the beach. Each is complete with full kitchen and there is a...
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    $140
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    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Housekeeping...
    • Housekeeping...
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every evening, having a cup... View all property information
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    1 / 24
    5 of 5 stars (6) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    See my website: www.AwayToParadise.com What's New: As an owner of this condo which I often stay at with my family I always try to improve and make our guests and my family feel as comfortable and pleasant as I can. In Summer 2014 our condo was upgraded with a brand new 55' flat screen Smart... View all property information
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    5 of 5 stars Reviewed September 22, 2014
    If you think that Florida off-season cannot be enjoyable, think again! We have just spent 2 weeks in September, stayed in #303 and had a fabulous vacation. Below are some...
    5 of 5 stars Reviewed August 20, 2014
    It was the best vacation in last 20 years! Property location was great, just a few steps away from the beach and nice swimming pool. Unit was very clean, newly renovated...
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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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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Beach on Longboat Key - New Gulf Front Condo # 225 ~ Beach Front Special ~ 1 Bedroom from $129/nigh This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach... View all property information
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    $99
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    1 / 18
    Studio / 1 Bathroom / Sleeps 3
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    The Beach on Longboat Key - New Gulf Front Condo # 103 ~ Beach Front Special ~ Studio from $99/nigh This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the... View all property information
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    $199
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    1 / 15
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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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    $195
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    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • 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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    $1,400
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • 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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    $214
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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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    $3,500
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    1 / 18
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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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    $171
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Welcome to your home away from home! Spread out in this beautifully remodeled 3 bedroom top floor unit, soaking in the water views and privacy of the small community of Longboat Landing. Whether you stay for a few nights, weeks, or months, there is plenty to see and do in between long bouts of... View all property information
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    5 of 5 stars Reviewed July 13, 2014
    We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
    5 of 5 stars Reviewed July 9, 2014
    Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Fishing...
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    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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    $178
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy a vacation filled with extras when you stay at this lovely 3 bedroom, 2 bath Buttonwood Harbour condominium. An attractive complex located at the south end of Longboat Key, Buttonwood Harbour offers a variety of amenities to suit the needs of every vacationer, beginning with a large, heated... View all property information
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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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    • Balcony
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    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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    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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    $250
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    1 / 6
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    • 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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    $190
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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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    $910
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Gym
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    About this property
    Directly across the street from the beautiful Gulf of Mexico! Amenities in the unit include Fios internet, 2 flat screened TVs with cable. Windward Bay is a low-density complex offering protected under building parking, extra storage, deeded access to Longboat Key's pristine beach within a short... View all property information
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    $167
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    1 / 41
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • 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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    $145
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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • 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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    $175
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    1 / 8
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • 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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    $1,750
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    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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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    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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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • 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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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    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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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    Set on a 30 acre private island a few hundred yards off North Longboat Key, this new water front home (completed in 2012) will provide an island vacation experience for you and your family like no other. The house has 2 bedrooms, an outside sleeping porch/bunk bed, along with 2 1/2 bathrooms and an... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    3 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    This Gulf Front Condo is tastefully decorated and is completely ready for you to enjoy. The spacious condo features a master suite bedroom and bathroom as well as a guest bedroom and a second full bath. The master bedroom has a king sized bed with top of the line mattress and plenty of... View all property information
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    5 of 5 stars Reviewed April 16, 2015
    I along with my husband, daughter, and son-in-law spent a relaxing week on Longboat Key for Spring Break. The island itself offers beautiful beaches and sunsets and is calm...
    1 of 5 stars Reviewed August 31, 2014
    After a long flight from the UK and a 2.5 hour drive from Orlando we were pretty jaded and glad to have finally arrived at our destination, we were informed by the owners that an...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    The Shore is a Gulf-front complex located near the north end of the island, with exquisite views from everywhere on the property. If you treasure your time on the beach relaxing in the sun, you couldn't pick a better spot. Close your eyes and imagine the sound of the wind whispering through the... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Lovely 1 bedroom 1 bath rental unit on the second floor. The master bedroom has a king bed and the sofa in the living room is a queen size sleeper sofa. This condo is freshly painted throughout, nicely furnished and has skylights in the ceiling for lots of light. This unit is located close to the... View all property information
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    6 Bedrooms / 6 Bathrooms / Sleeps 20
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    About this property
    Looking for tropical seclusion on a private island? Georgous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and relaxation.... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    You'll enjoy the feel of an old-fashioned Florida beach vacation in this quiet, secluded 8-unit complex nestled on the shores of the Gulf of Mexico at the north end of Longboat Key. This is the definition of the simple life! Australian Pines whisper their invitation to stay and relax for a while.... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this sought-after resort complex, you'll find all sorts of amenities just outside your door, or across the street on the... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    This second story private mother in law apartment may just be the prettiest waterfront hideaway on Longboat Key. The owners spared no expense when they built this luxury addition to their home, wanting to give their guests the best possible resort experience. With hand-hewn hardwood floors, solid... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    On beautiful Sarasota Bay in a lush tropical setting, Harbour Bay Club is on Dream Island, only a short walk to the famous beaches of Longboat Key. Comfortably and stylishly decorated, this condo offers stunning views of the Bay from both the living area and the master bedroom. There are two... View all property information
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    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    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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    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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    About this property
    Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses. It's easy to see why people love to stay at this beautiful, sprawling resort. A friendly guard at the gate will welcome you into a lushly landscaped compound, and will direct you down a winding tree-lined... View all property information
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    About this property
    Will you be the lucky one to take advantage of this VERY RARE OPPORTUNITY to rent for the season at The Player's Club on Longboat Key. This gorgeous complex, featuring four mid-rise buildings facing the Gulf of Mexico, offers only a handful of rentals, most of which have been tenanted by the same... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    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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    4.5 of 5 stars (20) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    April 11 is the earliest opening for a rental stay. ++++++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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    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...
    2 of 5 stars Reviewed January 14, 2015
    Although it is actually bizarre to book an expensive double house for only 2 ladies we did so, because we wanted to treat ourselves when we saw the photo on the VRBO website of a...
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    4.5 of 5 stars (11) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    20% Discount offered for the remaining availability in 2014 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, only two units in this building. Our condo is the 1st floor unit... View all property information
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    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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    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.