We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Condos and Beach Rentals in Longboat Key, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    $0
    $177 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Travelers to Longboat Key are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    1400 sq ft free standing villa Our villa has 2 bedrooms, 2 bathrooms, living/ dining room, full kitchen and two bonus rooms. It is located on the bay which comes into the center of the community and features a marina - manatees and dolphins have been known to stop by! .Our unit is close to the... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Roomy one story villa with views of Bayou , pool and steps to private beach. Private beach conservancy offers tennis, shuffleboard, bocci ball, cabanas, grills and private beach chairs. Large master suite with roomy walk in closet. Bonus small bedroom with twin bed and dresser and hall bath.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Children's Pool
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to the Longboat Key Sarasota's most enjoyable vacation spot ever. If you are ready to relax and enjoy life our rental home is waiting for you. See my units website: AwayToParadise Up to 4 person private accommodation in our 1 Bedroom / 1 Bath island-side unit completely renovated,... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Magnificent 3 bedroom, 2.5 bath beach front condominium (3 month minimum stay) The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic location is on the south end of Longboat Key just minutes from downtown Sarasota and St.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Sauna
    • Satellite TV
    • DVD Player
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    * CONDE NAST VOTED LONGBOAT KEY THE SECOND BEST ISLAND DESTINATION IN NORTH AMERICA * Located on fabulous Longboat Key approximately 3 miles south of Anna Maria island, 6 miles north of Armand's Circle at Windward Bay.This 27 acre condominium complex situated between the Gulf Of Mexico and the... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 6
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    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
    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...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Shared Outdoor Pool...
    • Hot Tub
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful Gulf View unit, all updated. Screened in lanai overlooking the gulf - wake up, take your coffee/tea and gaze out over the pristine waters of the gulf. Awaken each morning to the view from the sliders in the spacious master bedroom. Enjoy the beach as well as the Bay in this unique Gulf... View all property information
    Location Information
    Longboat Key, Florida
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • 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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Patio
    • Air Conditioning
    • Waterfront
    • Porch
    • Wi-Fi
    • Balcony
    • Grill
    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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Porch
    • Satellite TV
    • Washer
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Designer's hidden home: 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 & TV Our Venetian Villa is nestled on the placid Longboat Key. With a short drive from the airport, Ringling Museum, St.... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful, spacious 2/2 condo on Longboat Key available for 2016 season! Newly remodeled with designer kitchen, high-end appliances, and modern furnishings. Completely turnkey stocked with all essentials. Condo offers canal and bay views. Washer/dryer in unit. Community features three pools,... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 7
    5 of 5 stars (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 1 week ago
    This was an exceptional find for us. The unit was very clean, and every attempt was made to make sure we were comfortable. We enjoyed our "home away from home" and will be...
    5 of 5 stars Reviewed December 20, 2015
    If you are looking for peace and QUIET DIRECTLY on the beach this is the place. We love traveling with all our stuff in the car and being able to have a kitchen. We found our "go...
    See all reviews
    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • 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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed August 10, 2015
    What a Villa, one of the best I have had the pleasure of staying in during my 15th visit to Florida. Many mod cons, some a little too modern for me, so that's where your teenage...
    See all reviews
    Studio, 1 Bathroom, Sleeps 3 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Private Outdoor...
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ocean Beach Front Special From $99/night Special Studio ~ 10% Off April 2 - April 30 . 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 condo, so what... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • DVD Player
    • Housekeeping...
    • Hot Tub
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    We just purchased this property and completely remodeled it. It has a new kitchen with granite counter tops, stainless appliances, and wine cooler. All new furniture and a 48 in TV in the living room and new central A/C. It is located in the middle of longboat key with shopping and restaurants in... View all property information
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Grill
    • 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
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Longboat Key, Florida 34228
    Get the List
    1 / 9
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Grill
    • Patio
    • 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
    Location Information
    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...
    See all reviews
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Internet Access
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Perfect holiday apartment that is continually renovated. Building was completely renewed in 2008. With 103 sq. m. and balcony, accommodation for up to 5. With all imaginable furnishing, e.g. full HD TV, free Pay TV in a great quality in every room, CD stereo system, Blu Ray DVD, High Speed... View all property information
    Location Information
    Longboat Key, Florida
    1 / 19
    3.5 of 5 stars (3) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool...
    • Patio
    • Air Conditioning
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beach in/Beach out Condo (Sleeps 6 - in 2 queen beds and 2 more in a queen sofa bed) Rarely will you find spectacular beachfront views AND direct walking access to the magnificent white sand beaches of Longboat Key. This “beach in – beach out” condo is just fifty steps from the Gulf of Mexico!... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed July 9, 2014
    My sister and I stayed 3 nights here and wished we had it all week. This location was excellent for our morning walk/run exercise and the beach was beautiful! We saw a sea turtle...
    5 of 5 stars Reviewed May 15, 2014
    The 1 bedroom condo was very clean and just like posted pictures. 1st floor patio exit to beachfront was nice. I'm used to staying up higher and watching views from a balcony, but...
    See all reviews
    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Balcony
    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    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
    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...
    5 of 5 stars Reviewed March 4, 2010
    The home was beautiful, all the amenities. Great location. We had no issue at all with the process of renting, made our reservation, paid and went. Everything was smooth, just how...
    See all reviews
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Waterfront
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Patio
    • DVD Player
    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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Waterfront
    • Satellite TV
    • DVD Player
    • 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
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida
    1 / 49
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    • Patio
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located near the historic town of Longboat at the north end of Longboat Key, this Key West-style home is located less than 150 yards from Whitney Beach and the Gulf of Mexico. One of 16 unique homes built by famed architect Frank Folsom Smith, on property formerly owned by the long-time resident,... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Set on 2 acres of land on a private island, this new home (completed in 2010) will provide an island vacation experience for you and your family like no other. The house has 4 bedrooms and 4 bathrooms and an outdoor shower. The two upstairs 2-room bedroom suites sleep up to 5 each, and all bedrooms... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed September 1, 2015
    The perfect place for a family vacation. The home, the property, the beach, and the location were all top notch. It exceeded my expectations. The owners were very accomodating and...
    See all reviews
    1 / 28
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • DVD Player
    • Waterfront
    • Washer
    • Air Conditioning
    • Patio
    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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed October 7, 2015
    Better than I had hoped! Lovely second floor condo, well furnished and perfectly located. I arrived on a Thursday. Ian in the office was very pleasant and helpful. My unit was...
    4 of 5 stars Reviewed August 14, 2015
    I did not stay in this unit. I was in 220, and my mother in law in 215. 215 was a larger floor plan than 215, but had the same # of bedroom/bathrooms. In this complex, some...
    See all reviews
    1 / 31
    5 of 5 stars (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Balcony
    • DVD Player
    • Washer
    • Satellite TV
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ***20% Discount for remaining available dates in 2015*** 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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed July 6, 2015
    This is my 2nt time renting this property and I highly recommend it. It is the perfect place to relax & unwind. Beach is great & Ramona makes the whole renting process easy...
    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...
    See all reviews
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Private Outdoor...
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Longboat Key 2 Bedroom 2 Bath Condominium at Seaplace (2 month minimum stay) This newly remodeled and updated, 2 bedroom 2 bath, open living area condominium is tastefully decorated and in immaculate condition. A two month minimum stay is required. Luxury vacation rental properties like Seaplace... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This exclusive beach house is located on the waters edge, directly on the Gulf of Mexico on prestigious Longboat Key. When you open the back door, walk out onto the pristine private beach and into the warm waters of the Gulf. This modern luxury property is newly renovated and has all the amenities,... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Balcony
    • Hot Tub
    • Terrace
    • DVD Player
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Live the Florida lifestyle in this beautiful, comfortable 4 bedroom, 3 bath private home located in the Sleepy Lagoon on the quaint end of Longboat key. This home sleeps 8 - 10 people. Offering a private, heated pool. In the back, you have your own private dock on the deep-water canal that will... View all property information
    Location Information
    Longboat Key, Florida
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Satellite TV
    • Washer
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining area. Quiet upscale residential neighborhood. Two minute walk to a quiet clean... View all property information
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Porch
    • Satellite TV
    • Outdoor Dining Area
    • Patio
    • Washer
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 17
    6 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • DVD Player
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 13
    4.5 of 5 stars (23) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Grill
    • Washer
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ++++++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. TOP 5 REASONS TO VACATION AT THE... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed January 1, 2016
    This is a very spacious condo that is fully equipped and easily accommodated the 8 of us. Great AC, 3 tvs, bicycles, bbq pit, etc. Close to the beachand includes access to a...
    5 of 5 stars Reviewed July 19, 2015
    We were really happy to rent Castle in sky after looking at many travel sites. We found nothing that could hold 9 women on Longboat Key unless we wanted to pay twice as...
    See all reviews
    1 / 44
    4 of 5 stars (1) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    • DVD Player
    • Waterfront
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed April 27, 2015
    I have had my eye on this house for 2 years now. Boy am I glad that I finally pulled the trigger and decided to stay here. Traveled with my wife, two children ages 2&4 and...
    See all reviews
    1 / 41
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Parking
    • DVD Player
    • Patio
    • Washer
    • Waterfront
    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
    Location Information
    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...
    See all reviews
    1 / 10
    5 of 5 stars (15) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    ****Please go to longboatbeachcom .**** for more information. ***I DO NOT ACCEPT BOOKINGS ONLINE THROUGH TRIPADVISOR*** I will email you a quote from my booking program. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit.... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed August 5, 2015
    We were traveling with some friends and enjoyed our stay at this condo. It was clean and close to the beach. The condo is right across the street from the public beach access. We...
    5 of 5 stars Reviewed August 1, 2015
    I can't say enough good things about this darling condo we stayed at here in Longboat Key. The view from the balcony is beautifull. Looking at the other units here, I think...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Ocean Views
    • Washer
    • Waterfront
    • Satellite TV
    • DVD Player
    • Air Conditioning
    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 private patio and walk right out to the BEACH (25 seconds!) Magnificent condo 1100 sqft with open floor plan. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen with stainless steel... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Yard
    • Secure Parking
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Secluded 2-bedroom private home with open floor plan including living room, dining area and well-equipped kitchen. Screened in lanai facing canal, gardens and active wildlife. One king bedded room and one queen bedded room with abundant closet space. Two newly renovated baths, washer/dryer,... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 52
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Sauna
    • Air Conditioning
    • Ocean Views
    • Children's Pool
    • Waterfront
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Cancelation deal 6/14-7/29 $3500/44nites + tax&fees Also $4000/44nites 7/30/-9/12 & 9/13 -10/27 + tax&fees. Save $1100. 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 on your own... View all property information
    Location Information
    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...
    See all reviews
    1 / 17
    3.5 of 5 stars (2) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key. Unique Bungalow Canal Home on the North End of Longboat Key. If you have been putting off writing the next great American novel due to the lack of a peaceful setting then this quaint canal home may be just the place for you.... View all property information
    Location Information
    Longboat Key, Florida 34228
    3 of 5 stars Reviewed April 9, 2014
    This rental was was very clean and had every thing you would need on vacation. Very cute house with huge yard. Loved hanging on the screened in porch. Nice location off the...
    4 of 5 stars Reviewed March 18, 2014
    The cottage was well reflected by the pictures. Everything fairly new and clean. Beds comfortable, has everything. Area quiet but short drive to Bradenton and Holmes beaches, for...
    See all reviews
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Hot Tub
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • 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 is... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our condo is a third floor unit, which we are currently renovating. It will be a fully furnished, 3 bedroom, (one king bed, two twin beds, one queen sofa bed, one full sofa bed) 2 bath condo with a lovely Gulf front view from the living room and balcony. You will have direct Gulf of Mexico beach... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 23
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Condo Unit #405 at the Beachcomber This vacation spot is on prestigious Longboat Key, located directly on the Gulf of Mexico. This condo is on the 4th floor facing the bay. The condo includes living/dining rooms and a large balcony Fully equipped kitchen (frig, stove, microwave, dish washer, ice... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed January 3, 2016
    The Beachcomber was a great place for a family vacation. I slept in the in wall bed, it was just as cozy as the one back home. The private beach was pleasant. Also, the grocery...
    See all reviews
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our house is located on Longboat Key, outside of the city of Sarasota, on the west coast of Florida. There is an airport in Sarasota, as well as in Tampa, which is a little over an hour away. Longboat Key is pretty and green, and is linked, by bridge, to Anna Maria Island on the north, and to St.... View all property information
    Location Information
    Longboat Key, Florida 1234
    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.