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Villas in Longboat Key, FL

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    1 / 17
    6 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    About this property
    Our condo is a third floor unit, which we are currently renovating. It will be a fully furnished, 3 bedroom, (one king bed, two twin beds, one queen sofa bed, one full sofa bed) 2 bath condo with a lovely Gulf front view from the living room and balcony. You will have direct Gulf of Mexico beach... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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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... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 28
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Children's Pool
    • Ocean Views
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    About this property
    3 MONTH MINIMUM Elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool. Stunning mirrored and... View all property information
    Location Information
    Longboat Key, Florida 34228
    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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    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    **ONE WEEK MINIMUM RENTAL HOME** This casual beach home is just the right place to enjoy a laid-back, toes-in-the-sand vacation! Nestled on the shores of the Gulf of Mexico at the north end of Longboat Key, it's the perfect spot for relaxing days on the beach, followed by fabulous sunsets and... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    Location Information
    Longboat Key, Florida 34228
    1 / 10
    5 of 5 stars (15) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    ****Please go to longboatbeachcom .**** for more information. ***I DO NOT ACCEPT BOOKINGS ONLINE THROUGH TRIPADVISOR*** I will email you a quote from my booking program. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit.... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 5 August 2015
    We were traveling with some friends and enjoyed our stay at this condo. It was clean and close to the beach. The condo is right across the street from the public beach access. We...
    5 of 5 stars Reviewed 1 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...
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    1 / 23
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    THE BEACH ON LONGBOAT KEY - One 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 beach atmosphere. A heated pool overlooks the Ocean. The pictures of the beach and... View all property information
    Location Information
    Longboat Key, Florida 34231
    5 of 5 stars Reviewed 29 December 2015
    We thoroughly enjoyed our time in your beautiful condo on Longboat Key. The weather was perfect and the condo was absolutely lovely. You’ve done a beautiful job decorating – we...
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    About this property
    We just purchased this property and completely remodeled it. It has a new kitchen with granite counter tops, stainless appliances, and wine cooler. All new furniture and a 48 in TV in the living room and new central A/C. It is located in the middle of longboat key with shopping and restaurants in... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 41
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed 19 March 2015
    Casa Del Mar is located in a beautiful part of Long Boat Key. The beach is beautiful and F15 condo was only steps away from the beach. There were plenty of lounge chairs on the...
    5 of 5 stars Reviewed 4 July 2014
    This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a brand...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Balcony
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    • Air Conditioning
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    About this property
    Perfect holiday apartment that is continually renovated. Building was completely renewed in 2008. With 103 sq. m. and balcony, accommodation for up to 5. With all imaginable furnishing, e.g. full HD TV, free Pay TV in a great quality in every room, CD stereo system, Blu Ray DVD, High Speed... View all property information
    Location Information
    Longboat Key, Florida
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
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    • Porch
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    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
    Location Information
    Longboat Key, Florida 34228
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Ocean Views
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    About this property
    This exclusive beach house is located on the waters edge, directly on the Gulf of Mexico on prestigious Longboat Key. When you open the back door, walk out onto the pristine private beach and into the warm waters of the Gulf. This modern luxury property is newly renovated and has all the amenities,... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 28
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
    • Private Garden
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    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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 2 weeks ago
    We really enjoyed our stay at this wonderful cottage. It is extremely well equipped and features everything you need for a great beach holiday, It is in a very quiet and nice...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    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 1100 sqft with open floor plan. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen with stainless steel... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Waterfront
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    • Pet-friendly
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    About this property
    Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 28
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 7 October 2015
    Better than I had hoped! Lovely second floor condo, well furnished and perfectly located. I arrived on a Thursday. Ian in the office was very pleasant and helpful. My unit was...
    4 of 5 stars Reviewed 14 August 2015
    I did not stay in this unit. I was in 220, and my mother in law in 215. 215 was a larger floor plan than 215, but had the same # of bedroom/bathrooms. In this complex, some...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Secluded 2-bedroom private home with open floor plan including living room, dining area and well-equipped kitchen. Screened in lanai facing canal, gardens and active wildlife. One king bedded room and one queen bedded room with abundant closet space. Two newly renovated baths, washer/dryer,... View all property information
    Location Information
    Longboat Key, Florida 34228
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    We offer two beautiful completely renovated in October 2015 1 Bedroom / 1 Bath apartment in the Beachcomber condo. Unit 303 and 401. Welcome to the Longboat Key Sarasota’s most enjoyable vacation spot ever. If you are ready to relax and enjoy life with our rental apartment is waiting for you.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining area. Quiet upscale residential neighborhood. Two minute walk to a quiet clean... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Roomy one story villa with views of Bayou , pool and steps to private beach. Private beach conservancy offers tennis, shuffleboard, bocci ball, cabanas, grills and private beach chairs. Large master suite with roomy walk in closet. Bonus small bedroom with twin bed and dresser and hall bath.... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 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... View all property information
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    Longboat Key, Florida 34228
    1 / 26
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. View all property information
    Location Information
    Longboat Key, Florida 33312
    5 of 5 stars Reviewed 2 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 6 May 2014
    Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This Exclusive Beachfront Condo Requires a Minimum, 3 Month Rental and Condo Board Application & Acceptance. Private Beach at your doorstep, behind the Gate at Longboat Key Club, with unbelievable views of the Sunset over the Gulf. 24/7 Concierge on premise. Minutes from Internationally... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Holiday paradise on the stunning Florida west coast on the island of Longboat Key. Stunning, elegant and luxurious complex. For selfcatering there is the kitchen with all necessities and modern devices. Of course, there is a washing machine and dryer avialable. First-class furnishing. Safe and... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy one of the best views of Sarasota Bay in the entire complex from this one bedroom, one bath second floor unit. Completely redecorated with new tile throughout, new furniture, and flat screen LCD TV's in both the living room and the bedroom, this end unit provides a higher degree of privacy... View all property information
    Location Information
    Longboat Key, Florida
    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 View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 13
    4.5 of 5 stars (23) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    ++++++Rated ' EXCELLENT' digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence. TOP 5 REASONS TO VACATION AT THE... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed 1 January 2016
    This is a very spacious condo that is fully equipped and easily accommodated the 8 of us. Great AC, 3 tvs, bicycles, bbq pit, etc. Close to the beachand includes access to a...
    5 of 5 stars Reviewed 20 July 2015
    We were really happy to rent Castle in sky after looking at many travel sites. We found nothing that could hold 9 women on Longboat Key unless we wanted to pay twice as...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Longboat Key 2 Bedroom 2 Bath Condominium at Seaplace (2 month minimum stay) This newly remodeled and updated, 2 bedroom 2 bath, open living area condominium is tastefully decorated and in immaculate condition. A two month minimum stay is required. Luxury vacation rental properties like Seaplace... View all property information
    Location Information
    Longboat Key, Florida 34228
    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... View all property information
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    Longboat Key, Florida 34228
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    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    All amenities including laundry. Grocery delivery available. Walking distance to private Longboat Key Beach, Durante Park (playground, nature trails, and mangroves) and fine dining and corner store. Condo is on the Sarasota Bay access canal, which leads to Gulf of Mexico. Ideal for boating,... View all property information
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    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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, &... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Offering a beautiful view of the gulf, but more economical than the other Gulffront condominiums at the Beach Castle Resort, the owners have spared no expense in renovating this condo.BEautifully decorated with a Florida flair! All the bathrooms have been remodelled and there is granite... View all property information
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    Longboat Key, Florida
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    1 / 31
    5 of 5 stars (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ***20% Discount for remaining available dates in 2015*** 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... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 6 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 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 few...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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. See my units website: AwayToParadise 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
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Designer'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 & 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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    Longboat Key, Florida 34228
    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ONE MONTH MINIMUM RENTALS ONLY. NO WEEKLY RENTALS. ONE OF LONGBOAT KEY'S BEST KEPT SECRETS! Longbeach is located at the north end of the island, right on the Gulf of Mexico. This quiet community offers a pool and two tennis courts. This charming 2nd floor walk-up has been lovingly furnished... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 17
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
    5 of 5 stars Reviewed 4 August 2015
    This unit was the absolute best! I couldn't handpicked it any better, in relation to its location/proximity to parking, beach access, pool access, etc. We could sit on the...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The perfect island getaway, located on the southern tip of Longboat Key with a beautiful beach and pool area. This deluxe unit features approximately 1700 square feet with a 52’ long, open beachfront lanai. The views cannot be beat! The beach is great and the pool and hot tub inviting too! The... View all property information
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    Longboat Key, Florida 34228
    1 / 1
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Located in a beach to bay resort absolutely beautifully landscaped with a private beach, large pool, tennis courts, fishing pier on the bay and many more wonderful assets. This ground level condo with no 2nd level has its own outdoor patio making it very private. Renovated in June 2015 this condo... View all property information
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    Longboat Key, Florida 34228
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    Ocean Beach Front Special From $99/night Special Studio ~ 10% Off April 2 - April 30 . This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what... View all property information
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    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Charming 1 bedroom 1 bath canal front unit. On canal with dock in the Back yard. A beautiful Beach, amazing 35 acre park, great restaurants All within a five minute walk. Great space in an amazing place! Everything you Need to relax for a long weekend, a week, a month, or a winter, or summer... View all property information
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    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.