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.

Holiday Vacation with Pools 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.
dd/mm/yyyy dd/mm/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
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $287 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Longboat Key are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    Clear All
    1 / 23
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 23
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 18
    4.5 of 5 bubbles (2) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ** From $99/night ** OCEAN FRONT SPECIAL 35% OFF ** Dec 11 - Jan 21 ~ 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 you see is what... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 18 March 2016
    We stayed at this unit for two weeks and found it an ideal place to stay overlooking the Gulf of Mexico on Longboat Key. The studio unit is cozy, but did not feel cramped with two...
    See all reviews
    1 / 17
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Ocean Views
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    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
    Location Information
    Longboat Key, Florida 34228
    4 of 5 bubbles Reviewed 1 June 2016
    We enjoyed our stay at the Seahorse Beach Resort and this unit was very nice. Everything is as pictured and laid out nicely. There were only 2 drawbacks. 1) The balconies are...
    4 of 5 bubbles Reviewed 17 February 2016
    We enjoyed this unit with the great views of the Gulf and sandy beaches!! There is a heated pool and the grounds and rooms are immaculate. New towels arrive each day and you...
    See all reviews
    1 / 18
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    other travellers 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
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    4 of 5 bubbles Reviewed 9 May 2016
    We needed three rooms with three bathrooms. There was one couple with a toddler, one couple and one adult. The unit was clean and spacious. The kitchen could have been better...
    See all reviews
    1 / 28
    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Shared Outdoor Pool...
    • Hot Tub
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beach Castle Resort BC6 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. 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... View all property information
    Location Information
    Longboat Key, Florida
    3 of 5 bubbles Reviewed 9 May 2016
    Stayed in unit 6 of at Beach Castle Resort the week of 4th of July. It was a last minute vacation opportunity and this was one of a very few units available on Longboat Key. We...
    See all reviews
    1 / 9
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers 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
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 29 June 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 bubbles Reviewed 2 May 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 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • DVD Player
    • Shared Outdoor Pool...
    • Internet Access
    • Hot Tub
    • Grill
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beach Castle Resort BC9 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Offering a beautiful view of the gulf, but more economical than the other Gulffront condominiums at the Beach Castle Resort, the owners have spared no expense in renovating this condo.BEautifully... View all property information
    Location Information
    Longboat Key, Florida
    1 / 18
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers 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
    • Child-friendly
    • Smoking allowed
    • 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 bubbles Reviewed 10 August 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
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 60
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Recently upgraded, second floor, Gulf front condo. Open concept kitchen, dining, living and family room with spectacular views of the Gulf. King size bed in Master bedroom with walk-in shower. Amenities include: flat screen televisions in den and both bedrooms, VCR/DVD and free high speed wireless... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 6
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Balcony
    • Air Conditioning
    • Grill
    • Washer
    • Parking
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 27
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Private Outdoor...
    • Hot Tub
    • Parking
    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Grill
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Waterfront
    • Washer
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Spacious, bright Bayside PET-FRIENDLY town home with partial Bay view and lush tropical landscaping. Unit has Full Kitchen, 2 LARGE BEDROOMS and 2 1/2 BATHS. Enjoy the fishing pier, large pool, tiki bar/restaurant. Come enjoy our Tropical Paradise! First level is extended parking garage. Second... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Private Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 29
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool...
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    637 Norton - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people. 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 people. Offering a... View all property information
    Location Information
    Longboat Key, Florida
    1 / 79
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Email me for a Virtual Tour link Top Cedars East Rental - 3 story, sleeps 4; Pets ok if small dogs up to 35 lbs. (no cats); Tommy Bahama style furnishings, newer floors, 1st floor is enclosed garage and foyer; 2nd floor is living room overlooking mangroves with pull out sofa that sleeps two and... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 24
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Balcony
    • Washer
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We offer 2 beautiful, completely renovated in October 2015 1 Bedroom / 1 Bath apartments in the Beachcomber condo. Unit 303 and 401 The guest will pay directly to condo management, this will be the most secure way of payment. See our condo website:AwayToParadise. com Welcome to the Longboat... View all property information
    Location Information
    Longboat Key, Florida 10312
    5 of 5 bubbles Reviewed 22 September 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 bubbles Reviewed 20 August 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...
    See all reviews
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Buttonwood Cove 205 - Condo 3 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. 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... View all property information
    Location Information
    Longboat Key, Florida
    Get the List
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Washer
    • Porch
    • Grill
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Holiday paradise on the stunning Florida west coast on the island of Longboat Key. Stunning, elegant and luxurious complex. For selfcatering there is the kitchen with all necessities and modern devices. Of course, there is a washing machine and dryer avialable. First-class furnishing. Safe and... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Balcony
    • Shared Outdoor Pool...
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Seascape 103 - Condo 3 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. 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... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Whitney Beach 145 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. Community pool. 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... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • Patio
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 16
    1 Bedroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Vacation in a little piec of paradise. Tastefully furnished unit overlooking the intercoastal waterway. Light and bright. Private Beach and poos access. Stacked washer and dryer in the kitchen, pull out sofa. SMall storage closet in foyer. Built-in kitchen table. Available Daily, Weekly,... View all property information
    Location Information
    Longboat Key, Florida
    1 / 70
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ***ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT!*** This 2400 sq ft four bedroom private home located in the exquisite Country Club Shores neighborhood, offers coastal access with its own dock, an enclosed pool overlooking the waterfront, and a gorgeous gourmet kitchen and... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 43
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 19 March 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 bubbles Reviewed 4 July 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 / 34
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Sauna
    • Ocean Views
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Million dollar view! Beautiful waterfront bay penthouse condo. Gorgeous panoramic views of Sarasota Bay and downtown Sarasota in this Windward Bay award winning condo complex! This condo has a bay view from every room, makes you feel like you are on a cruise. Starting April 2016 this condo is... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Housekeeping...
    • Washer
    • DVD Player
    • Satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ground floor Condo with two steps that lead out the back lanai to the white sands of Longboat Key. You can't get any closer to the beach than in this unit. The private beaches out the back door offer miles of shell collecting, sandcastle making, snorkleing, and dolphin sightings. Silver Sands... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 21
    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
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment.<BR>• Very private and quiet first floor, 1600 ft. unit with lush garden views.<BR>• Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom.<BR>• Guest... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 52
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    March-April cancellation now booking opportunity! Calendar months only. March discount rate $6000 PACK YOUR SWIM SUIT & 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 private gulf beach Watch dolphins &... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 14 April 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 bubbles Reviewed 8 August 2014
    You couldn't ask for anything more in a vacation retreat. Clean, modern, roomy accomodations. Steps to a white sand beach where the umbrellas and beach chairs are set up by the...
    See all reviews
    1 / 12
    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
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Patio
    • Air Conditioning
    • Grill
    • Parking
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 / 28
    3 Bedrooms, 4 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Ocean Views
    • Wi-Fi
    • Satellite TV
    • Sauna
    • Waterfront
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 23
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located on the Beautiful island of Longboat Key in Florida just off the coast of Sarasota, this condo (unit #405 on the 4th floor) peacefully placed right on the beach overlooking the magnificent Gulf of Mexico, comfortably sleeps up to 4 people in a very nice 1 bedroom with a set of twin wall beds... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 3 January 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
    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Hot Tub
    • Ocean Views
    • Satellite TV
    • Waterfront
    • Sauna
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Please note that the minimum stay is one month beginning on the first day of a month and ending on the last day. For rentals including February or March, the minimum stay is three months. This is the largest two bedroom apartment in the Beachplace condo complex and is located on the top floor... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 25 September 2016
    Thank you Melissa and Peter for handling a difficult situation. Our reservation which was made Feb. 2016 was changed 6 days before our arrival in Sept. due to some repair work on...
    See all reviews
    1 / 26
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Ocean Views
    • DVD Player
    • Patio
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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. Contact owner before booking View all property information
    Location Information
    Longboat Key, Florida 33312
    5 of 5 bubbles Reviewed 16 April 2016
    We were so excited to have such a beautiful, clean and well equipped suite. Kim has done such a great job. The gorgeous quiet beach was fantastic and the view was fabulous. We...
    4 of 5 bubbles Reviewed 6 May 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...
    See all reviews
    1 / 14
    5 of 5 bubbles (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Amenities & Details
    • Balcony
    • DVD Player
    • Internet Access
    • Satellite TV
    • Terrace
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position. ENJOY THE BEACH FROM YOUR BED, LIVING, DINING AND KITCHEN! Our studio sleeps 3 with new in 2016... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 6 September 2016
    This Seahorse studio was the perfect Beach Getaway. The space was very accommodating and comfortable, we were stuck in there for the first 2 days because of a storm and although...
    5 of 5 bubbles Reviewed 20 January 2016
    My husband and I stayed 2 nights at this mid-key studio condo. It has everything you need and the beach front location is amazing. The property is a former motel that has been...
    See all reviews
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Patio
    • Satellite TV
    • DVD Player
    • Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    LONGBOAT KEY - Beautiful Gulf to Bay. Bayport Beach and Tennis Club is a rare find. This award winning, amenity-rich community at sea’s edge is situated in the middle of Longboat Key. A popular residential enclave of 136 homes on 27 acres of picturesque gardens. Bayport is bordered by the Gulf of... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    One bedroom unit with King bed, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the gorgeous turquoise waters of the Gulf of Mexico. Sun, swim, walk the shoreline on this one of a kind beach with sand that is soft it will soothe your feet.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Washer
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    2 bedroom deluxe unit with King bed, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the beach. Plenty... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy your family vacation in the two beds,two baths 1,503 sf spacious condo,fully turn key equipped waiting for you to move-in. All utilities are free including hi speed internet, Wi-Fi, three flat TV's, landline phone, in-unit washer and dryer. Condo unit 203 located on the 2nd floor,... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Parking
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two bedroom unit with King bed, 2 double beds, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 8
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spacious 2 Bedroom (King in MBR and Queen in Guest BR) and 2 bath unit with Gulf View (North side) - watch sunset go down over the Gulf. Well decorated and furnished with a screened in lanai. Walk out to pool, hot tub, Har-Tru tennis and Gulf. 2 month minimum rental. Gym on site. 1 mile walking... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 23
    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
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 21
    4.5 of 5 bubbles (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 9 October 2016
    The shopping is just a short drive or bike ride away. There are lots of great restaurants close by. Sarasota has some fun, crafty areas and there is an outdoor craft fair on...
    5 of 5 bubbles Reviewed 7 October 2016
    Great place to stay - out the door right into the beautiful beach! Miles of white sand great for walking and gawking. Mgmt on site to deal with any issues although we've never had...
    See all reviews
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Gorgeous Bay Views! Turnkey Furnished Longboat Key Vacation Rental in popular Fairway Bay at Bay Isles. You will fall in love with this spacious 2 bedroom, 2 bath, end unit condo. The views from the 5th floor overlooking Sarasota Bay are stunning. Watch manatee, dolphin and exotic birds while... View all property information
    Location Information
    Longboat Key, Florida
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Florida lifestyle offers boating from the canal in your backyard. There is deeded beach access across the street. The Gulf of Mexico has stunning sunsets and miles of soft sandy beaches all within your reach. The Great Room has long canal views to Sarasota Bay. Newer, modern kitchen, saltwater... View all property information
    Location Information
    Longboat Key, Florida