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Cottages in Longboat Key, FL

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    All 75 Rentals in Longboat Key
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    Travellers to Longboat Key are booking January dates now. Secure your holiday rental today, and have the perfect trip.
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    $1,085
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    1 / 11
    5 of 5 stars (4) Excellent
    Studio / 1 Bathroom / Sleeps 2
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    $1,363
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    1 / 7
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    1 / 13
    4.5 of 5 stars (22) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    1 / 14
    5 of 5 stars (6) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
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    Amenities & Details
    • Water Views
    • DVD Player
    • Refrigerator
    • Waterfront
    • Balcony
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS On beautiful tropically landscaped Longboat Key, Florida you will find the natural beauty. Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position. ENJOY THE... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 9 August 2014
    Everything was perfect for 2 people. Nice decor, room set-up and proximity to beach. Quiet, mostly private feel (except for renovations being done next door). easy to arrange the...
    5 of 5 stars Reviewed 22 July 2014
    My husband and I enjoyed everything about our stay in this beautiful condo. Not only did we have a nicely decorated room inside, but our view was amazing outside. We were able to...
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    $234
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Water Views
    • Air Conditioning
    • Shared Tennis Court
    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to your home away from home! Spread out in this beautifully remodeled 3 bedroom top floor unit, soaking in the water views and privacy of the small community of Longboat Landing. Whether you stay for a few nights, weeks, or months, there is plenty to see and do in between long bouts of... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 14 July 2014
    We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
    5 of 5 stars Reviewed 10 July 2014
    Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
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    $3,212
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    1 / 5
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
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    Amenities & Details
    • Parking
    • Towels Provided
    • Private Outdoor...
    • Private Garden
    • Ocean Views
    • Air Conditioning
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Nestled among majestic palms and tropical landscaping, this Country Club Shores home is situated on a deep sailboat water with 113 feet of waterfront, and offers outstanding boating opportunities - all just two houses away from Sarasota Bay! Southern exposure on the canal side provides year-round... View all property information
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    Longboat Key, Florida 34228
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    $177
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    1 / 23
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Internet Access
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Water Views
    • Washer
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    *** SPECIAL From $119 per night *** August 3-8 , Aug 16-28 , Aug 31-Sep 4 , Sep 10-12 The Beach on Longboat Key - New 1 Bedroom Gulf Front Condo # 225 This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual... View all property information
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    Longboat Key, Florida 34231
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    $274
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    1 / 5
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Water Views
    • Stereo System
    • Internet Access
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This spectacular two bedroom condominium sits directly fronting on the Gulf in the middle of Long Boat Key. It was recently renovated from floor to ceiling and is beautifully decorated with warm, rich colors. The kitchen has stainless appliances, granite countertops and custom dark polished wood... View all property information
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    Longboat Key, Florida 34228
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    $1,646
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Children's Pool
    • Wi-Fi
    • Shared Tennis Court
    • Ping Pong Table
    • Ocean Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Million Dollar unobstructed ocean views. Right on the beach. Top floor.About a mile north from St Armand Circle.The condo has 2 bedrooms and 2 baths. Kitchen has granite and the place has everything you need.Just bring your clothes and food.Beautiful patio to enjoy the sunset views.Wi-Fi is... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $136
    / Night
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    1 / 18
    Studio / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Water Views
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    *** Ocean Beach Front Special ~ From $99/night or $350/4 nights *** Aug 2-5 , Aug 9-11, Aug 14-26 , Aug 31-Sep 4 , Sep 7-13. This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and... View all property information
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    Location Information
    Longboat Key, Florida 34228
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    $267
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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Water Views
    • Shared Tennis Court
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Groundfloor Beachfront! From large living and dining area with open kitchen just step outside to your private patio and walk right out to the BEACH (25 seconds!) Magnificent condo with open floor plan, very comfortable for 4-5 people. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen,... View all property information
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    Longboat Key, Florida 34228
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    $1,508
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    1 / 21
    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • Satellite TV
    • Patio
    • Water Views
    • Internet Access
    • Waterfront
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This one-bedroom, ground floor walk-out, has fantastic full gulf views and is only steps to the beach. It features a bright beach decor that will make your vacation in paradise truly memorable. The screened lanai is practically perched upon the sand! An added bonus is that it is a corner unit... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 27 November 2014
    Very clean appartment, well equipped kitchen for self catering, with all the kitchen utensils spotlessly clean, very good position on the beach. Quite and very peaceful. Would go...
    5 of 5 stars Reviewed 13 June 2014
    I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
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    $265
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    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Sauna
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Water Views
    • Hot Tub
    • Satellite TV
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    !!!!SUMMER SPECIAL!!!! JULY & AUGUST 2015 - ONLY 1,000 USD/WEEK OR 1,750 USD FOR 2 WEEKS Feel at home in this spacious waterfront condominium on Longboat Key with luxurious amenities, including heated pool and hot tub with views of the Sarasota Bay, tropical gardens, private boat dock and four... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 10 April 2015
    All 'first" for us. First time on Longboat Key, first time at spring training and first time using Tripadvisor/Flipkey. And the property - first rate : ). The location was great...
    5 of 5 stars Reviewed 16 October 2014
    The condo was spotless and well equipped with all of our vacation needs. The rooms are spacious and the view is stunning. We will never stay anywhere else when we go to Florida...
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    $185
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    1 / 17
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • DVD Player
    • Central Heating
    • Dishwasher
    • Refrigerator
    • Balcony
    • Microwave
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to the Longboat Key Sarasota's most enjoyable vacation spot ever. See my unit's on: AwayToParadise If you are ready to relax and enjoy life with our rental home is waiting for you. Up to 4 person private accommodation in our 1 Bedroom / 1 Bath island-side unit completely renovated,... View all property information
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    Longboat Key, Florida 34228
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    $203
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    1 / 9
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Patio
    • Stereo System
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful 2 bedroom condo for rent by owner on Sand Cay beach. Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. Please read our reviews, you won't be dissapointed! The condo is unit 208 at the... View all property information
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    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars 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...
    5 of 5 stars Reviewed 2 May 2014
    We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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    $309
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    1 / 20
    4.5 of 5 stars (16) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • DVD Player
    • Water Views
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    La Playa is a small 21-unit resort property of privately-owned condominiums available exclusively for weekly rentals twelve-months per year. Located on spectacular Longboat Key, a short drive from Sarasota on the wide sand beaches of the Gulf of Mexico, La Playa offers privacy and direct beach... View all property information
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    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed 8 July 2015
    management did a great job, from reservation to placing deposit, calling on day of arrival to make sure someone would be available for any last minute questions! clean unit, we...
    5 of 5 stars Reviewed 18 June 2015
    LaPlaya Condos are located literally on the beach. The condos are very clean and were perfectly suited for 2 adults and 2 teenagers. This area is not over crowded. Great...
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    $165
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Satellite TV
    • Private Fishing...
    • Air Conditioning
    • Shared Tennis Court
    • Watersports Nearby
    • Internet Access
    • Waterfront
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $343
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    1 / 16
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • DVD Player
    • Satellite TV
    • Waterfront
    • Washer
    • Air Conditioning
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front... View all property information
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    Longboat Key, Florida 34228
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    $267
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    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Dryer
    • Satellite TV
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Water Views
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the... View all property information
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    Longboat Key, Florida 34228
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    $199
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Stereo System
    • Ocean Views
    • Satellite TV
    • Water Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Doctor's hidden home: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. Wi-Fi & Cable TV Our Venetian Villa is nestled on the placid Longboat Key. With a short drive from the airport, Ringling Museum, St.... View all property information
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    Location Information
    Longboat Key, Florida 34228
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    $293
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Internet Access
    • Stereo System
    • Air Conditioning
    • DVD Player
    • TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
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    Location Information
    Longboat Key, Florida 34228
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    $369
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Washer
    • Waterfront
    • Satellite TV
    • Water Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Florida's SeaHorse Beach Resort on Longboat Key is located on the white sand beaches of the Gulf of Mexico. From the moment you arrive, the friendly and professional staff will welcome you to this Premier property where you can experience a panoramic view of the Gulf from your suite, or while... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $451
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    1 / 24
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Private Outdoor...
    • Refrigerator
    • Dryer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the beautiful turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Rate... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $261
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Washer
    • Water Views
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $1,920
    / Week
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Private Outdoor...
    • Private Fishing...
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • DVD Player
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $280
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    1 / 39
    5 of 5 stars (5) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Washer
    • Satellite TV
    • Stereo System
    • DVD Player
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    At our beautiful low-rise resort, located directly on the beach, our two-bedroom condominium is fifty paces from the pool and a private beach of soft white sand. 15F in popular Casa del Mar provides a spacious living room/home theatre (46 inch plasma TV & BlueRay Player), vaulted ceilings, and a... View all property information
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    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars 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 the...
    5 of 5 stars 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 brand...
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    $232
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    1 / 20
    4 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Waterfront
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our gulf front condominium has a beautiful view of the Gulf of Mexico not only from the balcony, but from the living room as well. We also have two other condos in this same resort that rent at lesser rates than shown below. We only recently purchased this condo, but in 2013 we replaced all the... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 20 May 2015
    I was celebrating my 30th wedding anniversary. I could not of picked a better place. The rental was super clean had everything you can imagine there for use. I will definitely...
    5 of 5 stars Reviewed 24 October 2014
    This place was very clean and updated. The extra amenities such as the cooler's and ice packs was a huge plus. We had plenty of bedding, and towels and bathroom stuff. It’s not a...
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Waterfront
    • Sauna
    • Air Conditioning
    • Shared Tennis Court
    • Children's Pool
    • Staffed Property
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    December Deal - $3000/26 nights Dec 2 - December 27 + tax & fees from listing. PACK YOUR SWIMSUIT & SMILE - THE REST IS HERE: Take the wooden walkway to swim in warm gentle azure gulf waters Walk softly past sea turtle nests & shell on your own private gulf beach Watch dolphins, shore... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 15 April 2015
    The two balconies and lanai overlooking the fabulous Gulf of Mexico provide a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably...
    5 of 5 stars Reviewed 30 November 2014
    Club Longboat is a wonderful development with excellent property managers. I stayed at Ed's condo from August thru October of 2014. Even during the 'low season', this area is just...
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    $259
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    5 of 5 stars (4) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Staffed Property
    • Internet Access
    • Ocean Views
    • Water Views
    • Waterfront
    • Air Conditioning
    • Housekeeping...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. View all property information
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    Location Information
    Longboat Key, Florida 33312
    5 of 5 stars Reviewed 3 July 2014
    My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at...
    4 of 5 stars 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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    $2,057
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • There Are Tennis...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Three bedroom cottage available weekly or monthly in the sought after North Longboat Key Village where resident peacocks visit daily. New beds, Linens, towels etc. Also available on VRBO #702686 Offered fully equipped unit reflecting its own unique style of a beach getaway in paradise, full of... View all property information
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    Longboat Key, Florida 34228
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Shared Tennis Court
    • Air Conditioning
    • Stereo System
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This updated, 2 bedroom and 2 bath condo has sweeping views of the Gulf of Mexico with spectacular sunsets and a quiet beach that stretches for miles. At the north end of Longboat Key, there are plenty of restaurants, shopping and cultural activities nearby. Other amenities include a heated pool,... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $245
    / Night
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Tennis Court
    • Water Views
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our condo has everything you will need for a relaxing vacation on the beach. The island of Longboat Key... ... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine.... View all property information
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    Location Information
    Longboat Key, Florida 4725
    From
    $549
    / Night
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our luxury vacation home will comfortably accomodate up to 12 guests and is located on a deepwater canal and has a dock suitable for a boat up to 30 feet in length. Beautiful Longboat Key beach is less than a 10 minute walk from the house and world-class shopping and dining at the famous St.... View all property information
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    Longboat Key, Florida 34228
    From
    $480
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    1 / 31
    5 of 5 stars (12) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Deck
    • Water Views
    • DVD Player
    • Satellite TV
    • Waterfront
    • Stereo System
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 7 July 2015
    This is my 2nt time renting this property and I highly recommend it. It is the perfect place to relax & unwind. Beach is great & Ramona makes the whole renting process easy...
    5 of 5 stars Reviewed 4 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 few...
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    $27,426
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    1 / 237
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Shared Tennis Court
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Water Views
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
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    Longboat Key, Florida 34228
    From
    $826
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $229
    / Night
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    1 / 41
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Stereo System
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
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    Longboat Key, Florida 34228
    From
    $4,800
    / Month
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Watersports Nearby
    • Water Views
    • Game Room
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. Fully furnished kitchen, washer and dryer (in unit), dedicated parking for 1 car directly in front of unit, with additional guest parking. Master Bedroom has a king sized bed, flat screen TV, en... View all property information
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    Longboat Key, Florida 34228
    From
    $195
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    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Stereo System
    • Patio
    • Dryer
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $13,713
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Waterfront
    • Stereo System
    • Air Conditioning
    • Shared Tennis Court
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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
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    Longboat Key, Florida 34228
    From
    $7,542
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 5
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Children's Pool
    • Shared Tennis Court
    • Wi-Fi
    • Waterfront
    • Sauna
    • Staffed Property
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 MONTH MINIMUM Elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool. Stunning mirrored and... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 21 November 2014
    This is a beautiful condo with lovely furnishings and every resort amenity one could ask for. Lots of walk in closets, flat screens, Jacuzzi tub, large rooms and great views...
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    $2,880
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Staffed Property
    • Shared Tennis Court
    • Ping Pong Table
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    • TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment. • Very private and quiet first floor, 1600 ft. unit with lush garden views. • Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom. • Guest bedroom with... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $2,400
    / Week
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    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Hot Tub
    • Water Views
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Large Gated Home on waterway - White Sand Beach only steps away. Our vacation home is spacious and beautifully furnished with 3 bedrooms and a large loft with sleeper-sofa, 3 full bathrooms, sleeps uo to 8 people, Perfect for families or couples. The home has a fully equipped gourmet kitchen with... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 29 May 2015
    We stayed here from may 9 to 16 with my 2 kids (3.5 and 2 years old), husband and my parents. The house was more than we could ask for. Plenty of room, very nicely decorated...
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    $1,220
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    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Linens Provided
    • Private Garden
    • Grill
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom 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... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $185
    / Night
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    1 / 18
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • There Are Tennis...
    • Wi-Fi
    • Watersports Nearby
    • Satellite TV
    • Elevator/Lift access
    • Children's Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to the Longboat Key Sarasota's most enjoyable vacation spot ever. If you are ready to relax and enjoy life our rental home is waiting for you. Up to 4 person private accommodation in our 1 Bedroom / 1 Bath island-side unit completely renovated, remodeled and refurbished in 2014, with new... View all property information
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    Location Information
    Longboat Key, Florida 34228
    From
    $151
    / Night
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    5 of 5 stars (13) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (13) Make Enquiry
    Amenities & Details
    • Water Views
    • Satellite TV
    • Stereo System
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Housekeeping...
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    ****Please go to www.longboatbeach.com .**** for more information. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best view in the building A large shopping plaza, Avenue of the Flowers, is behind the complex, offering... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 2 August 2015
    I can't say enough good things about this darling condo we stayed at here in Longboat Key. The view from the balcony is beautifull. Looking at the other units here, I think...
    5 of 5 stars Reviewed 18 April 2015
    Very nice condo!! Clean and has everything you would need for a comfortable stay. Fantastic access to the beach. Beautiful and clean beach. Love that the beach is not crowded at...
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    $1,363
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    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Watersports Nearby
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    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 in a residential area. One block to the grocery and the trolley stops right in front to take you to St Armands... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 20 May 2015
    We booked this unit last minute having never been to Longboat Key before. We were looking for peace and relaxation and we found it in this adorable 1 bedroom unit. Clean and fresh...
    5 of 5 stars Reviewed 3 May 2015
    Everything you could want in a vacation rental. We wanted to be right on the beach and this place offers that and more. Great kitchen,stocked with everything you need. Beach...
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    $1,190
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    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Water Views
    • Waterfront
    • Private Fishing...
    • Watersports Nearby
    • Air Conditioning
    • Internet Access
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 25 April 2015
    Lovely, well appointed, spotlessly clean beach house with tasteful decor and everything to make our stay comfortable and relaxed. Everything tastefully and thoughtfully done...
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    $207
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    1 / 10
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Stereo System
    • Private Outdoor...
    • Internet Access
    • Water Views
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    == Up to 25% discount on the regular resort rate == Special rates and discounts are available depending on time and length of stay. 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... View all property information
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    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 15 July 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 be...
    5 of 5 stars Reviewed 23 June 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 the...
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    $1,166
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    1 / 27
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Patio
    • Satellite TV
    • Refrigerator
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom one bath very affordable cottages are available weekly or monthly in the eclectic Longbeach Village where resident peacocks visit daily. New Beds, Linens, Towels etc.. Also available on VRBO #706230 Offered FULLY FURNISHED with each unit reflecting its own style of a beach getaway... View all property information
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    Location Information
    Longboat Key, Florida 34228
    Beachfront condos and bayside villas – your vacation rental on Longboat Key

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

    Longboat Key - the upscale coastal vacation destination

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

    Cultural treasures along Sarasota Bay

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

    Waterfront dining

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

    Visitor reviews aid vacation rental selection

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