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Longboat Key Villas

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    Travellers to Longboat Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 260 Rentals in Longboat Key
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    Beachfront Unit 4, Cozy Getaway for two1 / 11
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Las Hermanas/Starfish #3 Beach front Longboat Key1 / 7
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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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    Beachfront Longboat Key Studio #11 / 6
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Ocean Views
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Our second visit, stayed at this place again and will continue to do so. Everything you need is there. Always clean, right at beach and close to great places to eat. If you want...
    Reviewed 13 September 2016
    We love the place,was very clean.Had all the amenities.Loved having the beach at our doorstep.We will definitely come back.
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    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Las Hermanas/Starfish #2 Beachfront Longboat Key1 / 7
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Grill
    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2017
    My husband and I had the best vacation ever !!! We feel like we spent three weeks in paradise . Our unit was perfectly equipped for our vacation with everything we needed to...
    Reviewed 3 February 2016
    This was an exceptional find for us. The unit was very clean, and every attempt was made to make sure we were comfortable. We enjoyed our "home away from home" and...
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    About this property
    Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Air Conditioning
    • Ocean Views
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2016
    We couldn't have had a better time! The rental was comfortable and clean, and the view from the balcony was top notch. The beach was literally 300 steps from the condo...
    Reviewed 12 April 2016
    The unit is kind of small, but the private balcony made it! Wonderful view, private beach, and the fact that the complex is only 14 units made for a very intimate experience...
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    About this property
    THE BEACH ON LONGBOAT KEY - One Bedroom Gulf Front Condo * OCEAN FRONT SPECIAL AUGUST - SEPTEMBER * ~ This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. A heated pool overlooks the...
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    Longboat Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    • Waterfront
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 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...
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 18 March 2016
    We stayed at this unit for two weeks and found it an ideal place to stay overlooking the Gulf of Mexico on Longboat Key. The studio unit is cozy, but did not feel cramped with...
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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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    Beachfront Condo on the Beautiful Gulf of Mexico1 / 37
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Balcony
    • DVD Player
    • Washer
    • Satellite TV
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2014
    The location and view from the condo was outstanding. The condo came equipped with everything we needed. Easy access to gulf from back porch. Publix was close by to pick up a...
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    About this property
    Escape to Paradise with Incredible Sunsets and Balmy Breezes direct on the Gulf of Mexico with its beautiful White Sand Beaches stretching for miles. Private and very quiet, and features two bedrooms with a king size bed in the master suite and a queen size bed in the second bedroom, two full...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful condo right on the beach. AwayToParadise*com1 / 24
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Satellite TV
    • Washer
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2014
    If you think that Florida off-season cannot be enjoyable, think again! We have just spent 2 weeks in September, stayed in #303 and had a fabulous vacation. Below are some...
    Reviewed 20 August 2014
    It was the best vacation in last 20 years! Property location was great, just a few steps away from the beach and nice swimming pool. Unit was very clean, newly renovated...
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    About this property
    We offer two beautiful Gulf front, renovated 1 Bedroom / 1 Bath apartment in the Beachcomber condo. Unit 303 and 401. See our unit's info on AwayToParadise com We offer 2 units 303 and 401 in Beachcomber condo and Gulf v Condo located right on the beach across the street from shopping malls...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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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    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 30 June 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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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Longboat Key Retreat1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Parking
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2017
    We had a wonderful stay at this pet friendly condo. Everything was exactly what we expected from the description. Waking up to a view of the ocean made every day blissful...
    Reviewed 9 September 2016
    Located on it's own in very quiet area we did not feel safe as no other people about. House was not as clean as it should have been lots of bugs etc. well equipped, not as near...
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    About this property
    Comfortable Turn-Key Tropical Home is just a two-minute walk to the private sandy white beaches and dazzling blue waters of North Longboat Key. There is ten miles of sidewalks for your enjoyment to bike, jog, or walk as well as direct access from your backyard to Durante Park, a gorgeous Nature...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2016
    We needed three rooms with three bathrooms. There was one couple with a toddler, one couple and one adult. The unit was clean and spacious. The kitchen could have been better...
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Grill
    • Parking
    • Air Conditioning
    • 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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    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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    • 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise Cottage ~ RA569791 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 December 2016
    My husband and I, along with two other couples, just spent the most relaxing five days at Paradise Cottage. The name suits the house well. It was great. The house is very clean...
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    About this property
    Located between the nearby sandy white beaches and Sarasota Bay, enjoy plentiful water sports, fishing and relaxation. Paradise Cottage is a lovely vacation home located on Longboat Key between Sarasota and Anna Maria Island. The wonderful unit is just a 5min walk from the stunning white beaches...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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)
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Honeysuckle Cottage1 / 12
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2015
    We rented both the Luxury Log Cabin and the Tree House next door. Only complaints were in the Log Cabin - they need to put up drape/curtain in loft bedroom for those guests as...
    Reviewed 30 June 2015
    Cons:1. In the picture of the kitchen, it shows a crock pot and salt/pepper shakers. Neither were provided, so don’t plan on a crock pot meal like I did! And bring your own...
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    About this property
    1bed 1Bath Cottages Available Now For Summer Fun. Refurbished, new linens. Old Florida at it's best. Stroll or ride bike in one of the most quaint villages on the gulf coast of Florida. Keep an eye out for the Peacocks. One bedroom one bath cottage all new beds, Linens, towels etc. Cottage...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Location Information
    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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    • 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...
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Housekeeping Included
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet area in Longboat Key Village area, on Broadway. Short walk to white sandy beach, relax in the morning on the patio area. 2 large family rooms with Flat screen TV's, full kitchen with everything you need for making nice meals. Washer and dryer, king, queen, and 2 twins, 2 queen pull out sofa...
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • Balcony
    • Washer
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bath cottage all new beds, Linens, towels etc. Cottage available weekly or monthly in the Lovely North Longboat Key Village where resident peacocks visit daily. Sit out on your porch in the evening and relax or dine out at many of the water front restaurants. Offered FULLY FURNISHED with each...
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    Location Information
    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 25 September 2016
    Thank you Melissa and Peter for handling a difficult situation. Our reservation which was made Feb. 2016 was changed 6 days before our arrival in Sept. due to some repair work...
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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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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, 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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    Location Information
    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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    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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    * 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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    Longboat Key Beachfront  - Inn on the Beach 1-2071 / 20
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Inn1-207 SAVE $700 PER WEEK THIS AUGUST AND SEPTEMBER. $1400 per week reduced from $2100. 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Longboat Key Bayfront condo in Bay Isles1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 30 April 2017
    Enjoyed our stay in Bay Isles. The condo was very comfortable & the view of Sarasota day & night was awesome!! We would stay there again.
    Reviewed 30 November 2016
    We enjoyed our stay in the condo . a beautiful condo . wonderful location . recommend this condo when staying at Longboat Key.
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    Beautifully updated 2 bedroom, 2 bath Fairway Bay condo in double gated Bay Isles on South Longboat Key. Sweeping views of Sarasota Bay with downtown Sarasota in the distance from this 3rd floor unit with elevator. Fairway Bay has two heated pools, gym, tennis courts and access to the private,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Seascape Unit 1031 / 30
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 3 January 2016
    The Beachcomber was a great place for a family vacation. I slept in the in wall bed, it was just as cozy as the one back home. The private beach was pleasant. Also, the grocery...
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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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    Beach front condo in Longboat Key1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The quiet, pristine, white sand beaches of north Longboat Key await you at Silver Sands, a small, friendly AAA 3-Diamond resort set among tropical gardens on a sugar sand beach with panoramic views of the Gulf's turquoise waters. You'll find the on-site management friendly and...
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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 6 Quick View
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    VRBO 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...
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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 4 Quick View
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    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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    LONGBOAT KEY CANAL FRONT, SUMMER SPECIAL1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    'Very Welcoming & Peaceful' - several times quoted from our Guests Book. Best value on Longboat Key... Longboat Key is one of the most beautiful and secure barrier islands off of the west coast of Florida. Our townhouse is within a short walk to a nature lovers paradise - a 32 acre park which is...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spacious 2400 sqft 3 bedroom Spanish style house with a beautiful huge fully Italian tiled sunken living room. The house has large glass windows making it bright and well lit. The panoramic view of the canal is visible from all the areas including the 2 bedrooms. living room and dining room. You...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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    ***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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    Reviewed 19 March 2015
    Casa Del Mar is located in a beautiful part of Long Boat Key. The beach is beautiful and F15 condo was only steps away from the beach. There were plenty of lounge chairs on...
    Reviewed 4 July 2014
    This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a...
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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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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    6 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    About this property
    Looking for tropical seclusion on a private island? Gorgeous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private Island Polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and...
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    Longboat Key, Florida 34228
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 18
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    About this property
    Amazing totally furnished 5 Star beech front time share rental Property with PARTIAL ocean view. 2-bedrooms and 2-baths. Sleeps six comfortably: king size bed, two twin beds, and queen size sleep sofa. Wonderful free amenities. Check things out on line by looking up the Veranda Beach Club for...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Light, nicely decorated and well appointed condo in a small friendly two floor / 12 unit building located on bay side of Island and mere steps from private beach. Everything is provided for your stay. Located mid-island - a walk to nearby shops and terrific restaurants. Heated pool, fishing dock, &...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    Paradise Cottage is a lovely vacation home located on Longboat Key between Sarasota and Anna Maria Island. The wonderful unit is just a 5min walk from the stunning white beaches on the Gulf of Mexico. Your vacation home has 3 bedrooms and 2 baths and sleeps up to 7 people. The fully equipped...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Find your tropical oasis in sought after LONGBOAT KEY. Wake to sunrises over your dock overlooking Sarasota Bay and catch the sunset sinking into the Gulf of Mexico-. Enjoy Serenity in this lovely home, or By Bike or Car Minutes to St. Armands' Circle or jump into your Boat; down the Deep Water...
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    Longboat Key, Florida 34228
    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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    • Children's Pool
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    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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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Previous
    Beachfront condos and bayside villas – your holiday rental on Longboat Key

    Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family holiday condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family holidays, select rentals offer flexibility and value for holidays at the beach.

    Longboat Key - the upscale coastal holiday destination

    This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

    Cultural treasures along Sarasota Bay

    Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

    Waterfront dining

    Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat.Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

    Visitor reviews aid holiday rental selection

    You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.

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