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Longboat Key Cheap Rentals

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    Travelers to Longboat Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    23 Matching Rentals in Longboat KeyView all 94 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Whitney Beach 1451 / 28
    (1)Terrible
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Terrace
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    • Private Outdoor Pool (Heated)
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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. Distance to the Beach: 500 ft. 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    SUMMER- FURNISHED- 2 bedroom/ 1.5 bathroom unit is ready to go! Completely turn key, with bicycles,kayak and beach chairs! Amazing pool right on the Sarasota Bay! Great Kayaking right on the property! Private beach access on the Gulf of Mexico drive. The house has been totally remodeled with...
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Why stay with us? Sleeps 2 and small children. 1 bed, 1 Bath Cottages. One bedroom and 3 chairs. Dining table for 4 and outside patio for 4. We just update our cottage with New Queen bed, Linens, towels etc. We offer a full form mattress for children. Cottage available weekly or monthly in the...
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    Longboat Key, Florida 34228
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LONGBOAT KEY - Beautiful Gulf to Bay. Bayport Beach and Tennis Club is a rare find. This award winning, amenity-rich community at sea’s edge is situated in the middle of Longboat Key. A popular residential enclave of 136 homes on 27 acres of picturesque gardens. Bayport is bordered by the Gulf of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Patio
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    • Waterfront
    • Porch
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment. • 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Longboat Key Bayfront condo in Bay Isles1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
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    • Central Heating
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    Pet friendly
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    Reviewed April 30, 2017
    Enjoyed our stay in Bay Isles. The condo was very comfortable & the view of Sarasota day & night was awesome!! We would stay there again.
    Reviewed 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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    About this property
    Beautifully updated 2 bedroom, 2 bath Fairway Bay condo in double gated Bay Isles on South Longboat Key. Sweeping views of Sarasota Bay with downtown Sarasota in the distance from this 3rd floor unit with elevator. Fairway Bay has two heated pools, gym, tennis courts and access to the private,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Village of Longboat Key, 1 BR & 1 BA Comfortable Cottage Very Clean1 / 14
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Orchard is a Private Cottage. The garage is shared area, washer and dryer, beach chairs and 3 bikes for you to use. You have outside fire pit and lounge chairs. Housekeeping is off-site. Lawn service arrives in the am on Friday's The very quiet area in the North Village of Longboat Key, Fla. Enjoy...
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    Longboat Key, Florida 34228
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Beautiful, spacious 2/2 condo on Longboat Key available for 2016 season! Newly remodeled with designer kitchen, high-end appliances, and modern furnishings. Completely turnkey stocked with all essentials. Condo offers canal and bay views. Washer/dryer in unit. Community features three pools,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    ** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT **1 / 27
    (4)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Waterfront
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    • Ocean Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 14, 2018
    Location and proximity to the beach was great. The minuses were that the pool was often dirty with dead bugs. Also would be nice if unit had a screen door. Other units did...
    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...
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    About this property
    ** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT ** **SPECIAL MARCH 3-10 FOR $995 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Beachfront Unit 4, Cozy Getaway for two1 / 11
    (10)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 2018
    The location couldn’t be more perfect. Quiet and secluded beach. Your next door neighbors are locally owned beach houses so you won’t find the high rise hotels. The details of...
    Reviewed April 30, 2018
    Wonderful vacation. Everything was as good or better than expected. The beach was beautiful.I would recommend this place to anyone.
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    About this property
    Longboat Key Bargain on the beach. Our cozy get away on the beach is a favorite of many guests who enjoy the quiet beachfront. Just a simple beach hideaway for your next quiet stay at the beach It's neat studio apartment with patio and sandy beach at your door. The full size galley kitchen...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Waterfront
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Beach front condo in magnificent Longboat key. You will Love the the beautiful private Balcony with sensational beachfront views of turquoise Gulf waters. This unit is on the second floor with an elevator for easy access. The space is a roomy 1175 sqft with a full size kitchen living room...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Tranquility and rejuvenation is what you will find renting this apartment. This is an apartment, located on Longboat Key, between the bay and white sand beaches. With 1 bedroom, 1 bathroom, equipped kitchen and TV equipped living room, it can perfectly accommodate a couple. You do not need to leave...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tennis resort boasts gorgeous views of Mangrove wetland and is just a short walk from stunning gulf beaches! The community pool makes this a lovely family-friendly getaway. Find great bird-watching and wildlife viewing from the balcony, or stroll through Mangrove tunnels on the boardwalk....
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachfront Longboat Key Studio #11 / 6
    (7)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2018
    Studio #1 was very clean. It was perfect for my wife & I. We loved walking out the door & on being on the beach. It was just a few steps to the ocean. The beach was...
    Reviewed April 10, 2017
    Our second visit, stayed at this place again and will continue to do so. Everything you need is there. Always clean, right at beach and close to great places to eat. If you want...
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    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Spacious, bright Bayside PET-FRIENDLY town home with partial Bay view and lush tropical landscaping. Unit has Full Kitchen, 2 LARGE BEDROOMS and 2 1/2 BATHS. Enjoy the fishing pier, large pool, tiki bar/restaurant. Come enjoy our Tropical Paradise! First level is extended parking garage. Second...
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Longboat Key Retreat1 / 8
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    Comfortable Turn-Key Tropical Home is just a two-minute walk to the private sandy white beaches and dazzling blue waters of North Longboat Key. There is ten miles of sidewalks for your enjoyment to bike, jog, or walk as well as direct access from your backyard to Durante Park, a gorgeous Nature...
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    Longboat Key, Florida 34228
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • DVD Player
    • Sauna
    • Cable/satellite TV
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    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your family vacation in the two beds,two baths 1,503 sf spacious condo,fully turn key equipped waiting for you to move-in. All utilities are free including hi speed internet, Wi-Fi, three flat TV's, landline phone, in-unit washer and dryer. Condo unit 203 located on the 2nd floor,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ** DIRECT OCEAN FRONT SPECIAL MONDAY TO FRIDAY **1 / 27
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2018
    The view from the second floor balcony was wonderful. We were close to a Publix and not far from St Armand’s Circle. Good restaurants nearby. My friend had his birthday dinner...
    Reviewed September 23, 2017
    My husband and I had an enjoyable 3 night stay at this wonderful cozy conbo. We frequent Longboat Key to get our "beach fix" and have found a new favorite place. The...
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    About this property
    THE BEACH ON LONGBOAT KEY - One Bedroom Gulf Front Condo OCEAN FRONT SPECIAL 20% OFF WEEKDAYS ~ 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....
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    Location Information
    Longboat Key, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Spacious 2 Bedroom (King in MBR and Queen in Guest BR) and 2 bath unit with Gulf View (North side) - watch sunset go down over the Gulf. Well decorated and furnished with a screened in lanai. Walk out to pool, hot tub, Har-Tru tennis and Gulf. 2 month minimum rental. Gym on site. 1 mile walking...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Las Hermanas/Starfish #3 Beach front Longboat Key1 / 7
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Grill
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 26, 2018
    If you like to avoid the high-rise condos, this is your place. Close enough to "the circle" , Sarasota, and Siesta Key beach. But not so far as Bradenton Beach, where...
    Reviewed July 25, 2017
    We visited Las Hermanas again after three years. It was as beautiful as ever. This condo. is right on the beach and has every amenity you can think of. I have two teenage...
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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