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Longboat Key Vacation Rentals

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    Travelers to Longboat Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 11
    5 of 5 bubbles (6) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 6
    5 of 5 bubbles (5) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 17
    4.5 of 5 bubbles (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 12
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed April 17, 2017
    Our family really enjoyed our stay. The beach is at your doorstep and the view just amazing. The condo as you can see from the pictures is well equipped and very conformable. We...
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    1 / 25
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Ocean Views
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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... View all property information
    Location Information
    Longboat Key, Florida 34231
    5 of 5 bubbles Reviewed November 28, 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!!! Will...
    5 of 5 bubbles Reviewed April 12, 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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    1 / 7
    5 of 5 bubbles (12) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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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    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed December 10, 2016
    Beautiful view, great accommodations. Wonderful hosts. Couldn't ask for better. The place was very clean and well furnished with everything needed for a 2 week stay (except...
    5 of 5 bubbles Reviewed August 17, 2016
    My husband and I really enjoyed our stay. The place really felt like home. It was cozy, comfortable and clean. We especially loved the beach being steps away from the back door as...
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    1 / 37
    5 of 5 bubbles (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
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    • 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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed July 3, 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 / 7
    5 of 5 bubbles (10) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 3 weeks ago
    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 have...
    5 of 5 bubbles Reviewed February 3, 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 will be...
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    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
    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... View all property information
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    Longboat Key, Florida 34228
    1 / 18
    4.5 of 5 bubbles (3) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    *** OCEAN FRONT SPECIAL FROM $99/NIGHT *** OCEAN FRONT SPECIAL 20 % OFF * MAY 17-20 , JUNE 11-15 , JUNE 27-30 ~ 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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed March 18, 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 two...
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    1 / 18
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • 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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    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed August 10, 2015
    What a Villa, one of the best I have had the pleasure of staying in during my 15th visit to Florida. Many mod cons, some a little too modern for me, so that's where your teenage...
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    1 / 18
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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
    Location Information
    Longboat Key, Florida 34228
    4 of 5 bubbles Reviewed May 9, 2016
    We needed three rooms with three bathrooms. There was one couple with a toddler, one couple and one adult. The unit was clean and spacious. The kitchen could have been better...
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    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Multi-level 4 bed/3 bath home w/elevator just a short walk to the beach NOW AVAILABLE DUE TO CANCELLATION! We have reduced our seasonal rate on this property by $2000 so if you are still looking for a March 2017 rental....this is a real deal! If you are looking for a spacious home that provides a... View all property information
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    Longboat Key, Florida 34228
    1 / 13
    3.5 of 5 bubbles (3) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    About this property
    Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key. Unique Bungalow Canal Home on the North End of Longboat Key. QUICK WALK TO THE BEACH ! If you have been putting off writing the next great American novel due to the lack of a peaceful setting then this quaint canal home... View all property information
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    Longboat Key, Florida 34228
    1 / 21
    4.5 of 5 bubbles (21) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
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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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed January 30, 2017
    > We spent a week at La Playa on Longboat Key, Florida, in Unit 103A, a Gulf-front, ground floor unit with 2 bedrooms, 2 baths, full kitchen, and laundry in unit. It had a king...
    5 of 5 bubbles Reviewed October 9, 2016
    The shopping is just a short drive or bike ride away. There are lots of great restaurants close by. Sarasota has some fun, crafty areas and there is an outdoor craft fair on...
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Sauna
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    • Pet-friendly
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    • x
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    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    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... View all property information
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    Longboat Key, Florida 34228
    1 / 19
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Spacious 2 Bedroom (King in MBR and Queen in Guest BR) and 2 bath unit with Gulf View (North side) - watch sunset go down over the Gulf. Well decorated and furnished with a screened in lanai. Walk out to pool, hot tub, Har-Tru tennis and Gulf. 2 month minimum rental. Gym on site. 1 mile walking... View all property information
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    Longboat Key, Florida 34228
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    • x
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    About this property
    Whitney Beach 145 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. Community pool. Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this... View all property information
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    Longboat Key, Florida 34228
    1 / 8
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | 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
    5 of 5 bubbles Reviewed April 8, 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. Joan...
    3 of 5 bubbles Reviewed September 9, 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 to...
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    1 / 12
    4 of 5 bubbles (6) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • ?
    • x
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    • x
    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... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 bubbles Reviewed August 4, 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...
    3 of 5 bubbles Reviewed June 30, 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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    1 / 9
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • 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
    Location Information
    Longboat Key, Florida 34228
    4 of 5 bubbles Reviewed June 29, 2015
    I had to go to a work-related meeting in nearby Parrish, FL so I decided to rent a beach condo for a few days in order to mix work with leisure. I was traveling with my spouse...
    5 of 5 bubbles Reviewed May 2, 2014
    We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    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... View all property information
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    Longboat Key, Florida 34228
    1 / 28
    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Beach Castle Resort BC6 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Beautiful Gulf View unit, all updated. Screened in lanai overlooking the gulf - wake up, take your coffee/tea and gaze out over the pristine waters of the gulf. Awaken each morning to the view from... View all property information
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    Longboat Key, Florida 34228
    3 of 5 bubbles Reviewed May 9, 2016
    Stayed in unit 6 of at Beach Castle Resort the week of 4th of July. It was a last minute vacation opportunity and this was one of a very few units available on Longboat Key. We...
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    1 / 15
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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
    5 of 5 bubbles Reviewed March 26, 2017
    A beautiful and luxurious beach front property with private beach access and a lovely and whimsical outdoor shower. Our family enjoyed an incredible and memorable vacation!
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    1 / 23
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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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... View all property information
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    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed January 3, 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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    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    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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    Longboat Key, Florida 34228
    1 / 31
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed December 9, 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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    1 / 30
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Seascape 103 - Condo 3 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. You'll enjoy the feel of an old-fashioned Florida beach vacation in this quiet, secluded 8-unit complex nestled on the shores of the Gulf of Mexico at the north end of Longboat Key. This is the definition of... View all property information
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    Longboat Key, Florida 34228
    1 / 13
    3 of 5 bubbles (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... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 bedroom deluxe unit with King bed, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the beach. Plenty... View all property information
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    Longboat Key, Florida 34228
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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... View all property information
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    Longboat Key, Florida 34228
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    One bedroom unit with King bed, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the gorgeous turquoise waters of the Gulf of Mexico. Sun, swim, walk the shoreline on this one of a kind beach with sand that is soft it will soothe your feet.... View all property information
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    Longboat Key, Florida 34228
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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... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note that the minimum stay is one month beginning on the first day of a month and ending on the last day. For rentals including February or March, the minimum stay is three months. This is the largest two bedroom apartment in the Beachplace condo complex and is located on the top floor... View all property information
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    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed September 25, 2016
    Thank you Melissa and Peter for handling a difficult situation. Our reservation which was made Feb. 2016 was changed 6 days before our arrival in Sept. due to some repair work on...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    * DIRECT BEACH FRONT * * SPECIAL From $99 * June 27-29 Aug 13-18 Sep 4-7 Sep 19-23 . . 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 tastefully... View all property information
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    Longboat Key, Florida 34228
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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
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    Longboat Key, Florida 34228
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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... View all property information
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    Longboat Key, Florida 34228
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    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 sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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,... View all property information
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    Longboat Key, Florida 34228
    5 of 5 bubbles Reviewed 3 weeks ago
    Enjoyed our stay in Bay Isles. The condo was very comfortable & the view of Sarasota day & night was awesome!! We would stay there again.
    5 of 5 bubbles Reviewed November 30, 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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    Enjoy your family vacation in the two beds,two baths 1,503 sf spacious condo,fully turn key equipped waiting for you to move-in. All utilities are free including hi speed internet, Wi-Fi, three flat TV's, landline phone, in-unit washer and dryer. Condo unit 203 located on the 2nd floor,... View all property information
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    Longboat Key, Florida 34228
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    637 Norton - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people. Live the Florida lifestyle in this beautiful, comfortable 4 bedroom, 3 bath private home located in the Sleepy Lagoon on the quaint end of Longboat key. This home sleeps 8 people. Offering a... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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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    Longboat Key, Florida 34228
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    Enjoy a relaxing getaway in our exclusive Zilli Villa. This tranquil two bedroom gem is perfect for a romantic honeymoon, family vacation or a restful week long retreat. It is a fabulous home one of a kind. There is nothing like Long Boat on the Gulf other than Naples. Spread the Word Zilli... View all property information
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    Longboat Key, Florida 34228
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    ***ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT!*** This 2400 sq ft four bedroom private home located in the exquisite Country Club Shores neighborhood, offers coastal access with its own dock, an enclosed pool overlooking the waterfront, and a gorgeous gourmet kitchen and... View all property information
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    Longboat Key, Florida 34228
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    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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    Longboat Key, Florida 34228
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    Two Month Minimum Rental Required by Condo Association. This gulf-front Longboat Harbour Towers, sixth floor condo(4401 Gulf of Mexico Drive)has panoramic views of the Gulf of Mexico with NEW KITCHEN, BATHROOMS, AND WINDOWS. The sunny, cheerful interior encourages relaxation from the time you... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    The home is a cottage located in historic Longbeach Village in the North end of Longboat Key, Florida. The home is near both the beach and the intercoastal waterway, with some water views. The beautiful Longboat Key beach is walking distance, about five blocks away.<BR><BR>We purchased the home... View all property information
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    Longboat Key, Florida 34228
    Longboat Key Flight and Weather Info
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    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.