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.

Longboat Key Rentals with Pools

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Price
    per night
    $194 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Longboat Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    56 Matching Rentals in Longboat KeyView all 185 rentals
    Sort by:
    Default
    ~ OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT - MONDAY-FRIDAY ~1 / 17
    (3)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
    other travelers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Spacious Gulf Front beach condo on Longboat Key1 / 17
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    ** OCEAN FRONT SPECIAL 20% OFF **  Oct 7-23  Oct 30-Nov 11   Nov 20-30 **1 / 26
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travelers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Longboat Key Gulf-front 2 BR/2 BA, amazing views1 / 12
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2017
    Our family really enjoyed our stay. The beach is at your doorstep and the view just amazing. The condo as you can see from the pictures is well equipped and very conformable. We...
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Charming Beach House in Longboat Key/ pool/pet/dock1 / 18
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This house is a great place for vacation. We enjoyed all amenities provided. The house is fully equiped with everthing you need. Thank you very much.
    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
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    LaPlaya Condominium1 / 21
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2017
    We stay here every summer- rent multiple units for a family reunion. The property is right on the gulf with spectacular views. All of the units are perfectly appointed with...
    Reviewed June 30, 2017
    Loved this place! We stayed in 103A and it was very comfortable for my 92 year old Grandmother, 10 year old daughter, and my husband and I. It was important that we were on...
    Reviewed June 28, 2017
    This year was our 5th Summer at LaPlaya! We love it here! We stayed in different units since we always book last minute, so far we loved each unit. The condos are very well...
    Reviewed January 30, 2017
    > We spent a week at La Playa on Longboat Key, Florida, in Unit 103A, a Gulf-front, ground floor unit with 2 bedrooms, 2 baths, full kitchen, and laundry in unit. It had a...
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Gulf of Mexico Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Porch
    • Grill
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Beach Castle Resort 61 / 28
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 9, 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
    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 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Terrace
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Instant Book
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Multi-level 4 bed/3 bath home w/elevator just a short walk to the beach NOW AVAILABLE DUE TO CANCELLATION! We have reduced our seasonal rate on this property by $2000 so if you are still looking for a March 2017 rental....this is a real deal! If you are looking for a spacious home that provides a...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Save time - get the best Longboat Key rentals sent straight to your email!
    Get the List
    Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent1 / 23
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Beautiful Beach Condo, Family Friendly, Heated Pool1 / 9
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Sand Cay Beach Resort Ocean Views Luxury Apartment1 / 120
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 9, 2017
    Condo is right on the Gulf, terrace views and sunsets perfect. Location is close to shopping, restaurants, very walkable along the beach or the road. Well outfitted...
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit is ONLY available from August 26, 2017 - September 2, 2017! Please refer to my website (google white sands of Longboat Key, FL) for more pictures and details! Unit was renovated in 2016! This fully furnished 2 bed/2bath townhouse (bay side unit 113, refer to link at the bottom of the...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Balcony
    • Air Conditioning
    • Grill
    • Washer
    • Parking
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Longboat Key-Beachplace. Perfect Apt, Beach & View1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • Hot Tub
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Sauna
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 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...
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Ocean Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BEACHSIDE CONDO AVAILABLE NIGHTLY OR WEEKLY. Relax and enjoy full Gulf views and fabulous sunsets from this beachfront condo with heated pool. Take a stroll for miles on the white sand beach. This beachfront community provides one of the best beach getaways on Longboat Key. Open...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Gull is the perfect resort for complete relaxation in this lovely cottage on Longboat Key. We are offering week 37 of this timeshare. (Sept 16-23) Unit 10 is on the Bayside is fully equipped; has a four poster beds and wood burning fireplace. You won't find another resort quite like this...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Wi-Fi
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ~ DIRECT BEACH - OCEAN FRONT ~ * SPECIAL * Nov 29 - Dec 2 Dec 12-23 Jan 9-11 Jan 18-21 Please contact me about rates . This small complex is - AAA Approved and Superior Small Lodging Award Recipient for 2016. For your privacy, our unit is located on the second floor. Our one bedroom (4...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • Patio
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Outrigger Resort unit #31 / 36
    (1)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 9, 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
    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
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Inquiry
    Seascape Unit 1031 / 30
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Sauna
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Renovated in November 2016 our unit features direct gulf views from the living room, kitchen and master bedroom. Brand new appliances and fixtures throughout including in unit washer and dryer. Each bedroom has a flat screen TV, king size bed and an on-suite bathroom. The den has a queen...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Dec.24-30,2017 Available! BEACHFRONT RESORT- heated pool + tennis - discounts!1 / 13
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2017
    Great two bed/ 2 bath, located on the gulf. Friendly management, free use of laundry room. Beach lounge chairs and umbrellas available. It met all of our requirements- ! Would...
    Reviewed April 23, 2017
    This condo was absolutely exceptional. Beautifully furnished with lots of windows, air, and natural light. Very well maintained and extremely clean. The resort staff in the...
    Reviewed July 14, 2015
    This was my first stay at Sand Cay Beach Resort and I can't say enough positive things about my experience. I have been to Longboat Key on several occasions and was excited to...
    Reviewed June 22, 2015
    My wife and I stayed at the resort for one week in June 2015. I so wish we'd booked for 2 weeks. The apartment was lovely. No faults from us on the apartment, the pool area or...
    See all reviews
    About this property
    Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort on the exclusive island of Longboat Key. South facing balcony. Striking views of the beach from the balcony, and a glimpse of the bay from the bedrooms. Cathedral ceilings throughout, bright open kitchen with corian...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Gulf Breezes, Soft Sand! Your Beach Place1 / 43
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Parking
    • DVD Player
    • Patio
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
    Reviewed February 28, 2014
    Casa del Mar on Longboat Key is a beautifully landscaped property right on the beach. The grounds are carefully tended with lots of vine covered trellises, a flower and orchid...
    Reviewed September 29, 2011
    Casa Del Mar is a wonderful vacation resort on the shores of the Gulf of Mexico. The unit that I was in overlooked the pool and had a marvelous view of the beach and Gulf...
    See all reviews
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcomes you to a unique eight unit condominium. Nestled on Longboat Keys finest beach. Gulf Front offers an intimate villa ambience by combining privacy with luxuries of condminium living. Relax in this totally renovated 2 bedroom 2 Bath condo.Wake up and enjoy your breakfast on your screened...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Beach front condo in Longboat Key1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation Rental: Seaplace, a gulf-side community on south Longboat Key. This stunning turnkey furnished 2 bed, 2 bath 4th floor unit (elevator provided) provides everything you need to enjoy a beach vacation. Amazing amenities include gated entry, lush landscaping, recreational trails, on-site...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 BEDROOM, LONGBOAT KEY, DIRECTLY ON THE BEACH1 / 24
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Ocean Views
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 11, 2017
    We stayed in unit 245 which was very nice, clean and well kept. Our only complaint was the cable TV. It lacked certain channels and would cut in and out. The A/C unit was in the...
    Reviewed April 16, 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...
    Reviewed May 6, 2014
    Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
    Reviewed November 14, 2013
    Just returned from Longboat Key. Loved staying at the Diplomat! The beach is RIGHT there...as in 20ft from your door! If you're looking for lots of things to do right at your...
    See all reviews
    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
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WestChester 304A- Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. Welcome to Paradise! This 2 bedroom 2 bath conod is on the 3rd floor with 2 private balconies where you can enjoy the sound of the rolling waves and some of the most spectacular sunsets in Longboat Key. There is a king size...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Washer
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Internet Access
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 34228
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Wi-Fi
    • Balcony
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sand Cay Resort is centrally located on beautiful Longboat Key near restaurants and shopping. The resort has a heated pool, shuffleboard, basket ball and full tennis court, in addition to an immaculate private white sandy beach. We have a free laundry room, barbecue area and elevator. Our remodeled...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious villa on gulf features a heated pool, 3 beautiful terraces, fully-equipped gourmet kitchen & outdoor BBQ grill, fine art & sculpture, high-speed internet, flat screen televisions, video & board games, bicycles, ping pong, & much more. Located near the historic town of Longboat at...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Longboat Key Beachfront 2 BR Condo - Inn on the Beach 1-2071 / 20
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Balcony
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inn1-207 The perfect island getaway, located on the southern tip of Longboat Key with a beautiful beach and pool area. This deluxe unit features approximately 1700 square feet with a 52' long, open beachfront lanai. The views cannot be beat! The beach is great and the pool and hot tub inviting...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    SeaHorse Beach Resort Studio 247 Longboat Key FL1 / 14
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    Lovely studio beach front affording amazing views for sunsets. Well kept and equipped for stress free stay. ONLY drawback was smoking neighbours, despite requests from...
    Reviewed 2 weeks ago
    Tropical, lush location in a beautiful area with great beach/pool right downstairs The unit was super clean and comfortable for 2 people!
    Reviewed September 6, 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...
    Reviewed January 20, 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
    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 2017...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated unit with tile floors and granite counter tops. Unit has full washer and dryer. Lanai is enclosed with glass sliders for extra functionality. First floor unit has beautiful bay views and is accessible by stairs or elevator. The master bedroom overlooks the bay and the second...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Washer
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit is a two bedroom condo available for rent during 4-7 thru 4-21 (Saturday to...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Paradise! Spectacular Gulf view from completely renovated unit in Turtle Crawl Inn Resort on Longboat Key, FL View! View! View! Welcome to our condo hotel. Our onsite office with friendly staff is here to help you with all of your needs. You’ll escape to our Tropical Paradise with 200...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • DVD Player
    • Sauna
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 10/11 is a one bedroom condo available for rent during 4-7 thru 4-21. (Saturday...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 12 is a two bedroom condo available for rent 4-14 thru 4-21(Saturday to...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Ocean Views
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two Month Minimum Rental Required by Condo Association. This gulf-front Longboat Harbour Towers, sixth floor condo(4401 Gulf of Mexico Drive)has panoramic views of the Gulf of Mexico with NEW KITCHEN, BATHROOMS, AND WINDOWS. The sunny, cheerful interior encourages relaxation from the time you...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a relaxing getaway in our exclusive Zilli Villa. This tranquil two bedroom gem is perfect for a romantic honeymoon, family vacation or a restful week long retreat. It is a fabulous home one of a kind. There is nothing like Long Boat on the Gulf other than Naples. Spread the Word Zilli...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    Private condo in serene setting  beach and bay1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Porch
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***Minimum 30 Day Rental*** Longboat key offers uncrowded beaches, great food and serene accommodations. Bayport Beach and Tennis Club is a beach to bay complex made up of 2 story buildings that offer privacy in a very serene and relaxing environment. This condo is a 2 bedroom 2 bath condo that is...
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Previous
    Longboat Key Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    73° 56°
    November
    69° 50°
    December
    68° 49°
    January
    List your property
    Owner log in