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Holiday Rentals with Pools in Longboat Key

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    Travellers to Longboat Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    52 Matching Rentals in Longboat KeyView all 87 rentals
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    Spacious Gulf Front beach condo on Longboat Key1 / 17
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    THE BEACH ON LONGBOAT KEY - 1 Bedroom Ocean Front Condo  * SPECIAL AUG - SEP *1 / 25
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Longboat Key Gulf-front 2 BR/2 BA, amazing views1 / 12
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    *** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT WEEKDAYS ***1 / 18
    (3)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 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...
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    About this property
    *** OCEAN FRONT SPECIAL FROM $99/NIGHT *** * AUGUST - SEPTEMBER WEEKDAYS * ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    LaPlaya Condominium1 / 21
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 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 28 June 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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Charming Beach House in Longboat Key/ pool/pet/dock1 / 18
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Outrigger Resort unit #31 / 18
    (1)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
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    • Waterfront
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    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beach Castle Resort 61 / 28
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Hot Tub
    • 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
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    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Terrace
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful Beach Condo, Family Friendly, Heated Pool1 / 9
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 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...
    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...
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    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...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sarasota Bay front house with unobstructed, beautiful, wide water views. Large, two story house has everything you need for your island getaway. House is furnished, updated and has a deeded beach access. Enjoy your oversized private pool, fishing pier, walk across the street to white sand Gulf...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
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    • 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Longboat Key-Beachplace. Perfect Apt, Beach & View1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • Hot Tub
    • Ocean Views
    • Satellite TV
    • Waterfront
    • Sauna
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Wi-Fi
    • Balcony
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * DIRECT BEACH FRONT * * SPECIAL from $99/night * Aug 6 -16 Sep 4-7 Nov 8-10 Nov 15-17 . 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 Persons Max) condo is...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be enchanted by our lovely Key West style home in historic, laid back Longboat Village at the north end of exclusive Longboat Key. Tastefully relaxed interiors are exquisitely complimented by a heated tropical pool area whose quiet, spa-like ambiance and sparkling waterfall will be yours to...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    • Waterfront
    • DVD Player
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    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
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Seascape Unit 1031 / 30
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
    • Terrace
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stunning Gulf of Mexico Sunsets VHBO #  43319151 / 46
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    • Sauna
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beach front condo in Longboat Key1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Housekeeping Included
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    • Ocean Views
    • Wi-Fi
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Private condo in serene setting  beach and bay1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Satellite TV
    • Parking
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    NEW SUMMER SPECIAL 25% off !! JULY/AUG~Gulf Breezes, Soft Sand! Your Beach Place1 / 43
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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...
    Reviewed 5 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...
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    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...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • Patio
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    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 5 Quick View
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    • Children's Pool
    • Ocean Views
    • Wi-Fi
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    • Sauna
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    • Air Conditioning
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • DVD Player
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    • Hot Tub
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    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,...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • DVD Player
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    • Porch
    • Grill
    • Patio
    • Internet Access
    • Air Conditioning
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    View! View! View! Welcome to our condo hotel. Our onside office with friendly staff is here to help you with all of your needs. See unit website AwayToParadise *com With vacation condo 403 you’ll escape to our Tropical Paradise with 200 feet of beautiful beach and awesome sunsets. This one bedroom...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 BEDROOM, LONGBOAT KEY, DIRECTLY ON THE BEACH1 / 26
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Ocean Views
    • DVD Player
    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 7 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...
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    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
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    Longboat Key, Florida 33312
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
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    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
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    • 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...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Parking
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
    • Patio
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    • 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. NOTE THIS UNIT IS ONLY AVAILABLE BETWEEN jUNE 1 AND SEPTEMBER 20 OF EACH YEAR. CHECK OUR CALENDAR FOR AVAILABILITY ON SPECIFIC DATES IN THAT RANGE. Fully furnished kitchen, washer and dryer (in...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    AUGUST 2017-SUMMER SPECIAL Beachfront resort - heated pool + tennis - discounts!1 / 26
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Balcony
    • Satellite TV
    • Air Conditioning
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    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 23 April 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...
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    About this property
    !!!! SUMMER SPECIAL AUGUST 2017 !!!! Stay between August 12 – August 24, 2017 for our low rate of $ 150.00/night (4 nights minimum) full week only $ 1,000.00 Rates do not include cleaning, booking fee and tax (Sand Cay standard prices: $ 195.00/night) Beautiful...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Washer
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    • Waterfront
    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
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    • Sauna
    • Grill
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    SeaHorse Beach Resort Studio 247 Longboat Key FL1 / 14
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • DVD Player
    • Internet Access
    • Satellite TV
    • Terrace
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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...
    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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    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....
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    Longboat Key, Florida 1234
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Satellite TV
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    • 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Waterfront
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Children's Pool
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful and clean condo that is just steps away from the gulf of mexico and its wonderful beach. Pool and workout facilities right next to condo. Condo has a master suite with a king size bed and a second bedroom with a queen size bed. We want to rent for two months at a time, so we are priced...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
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    • 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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