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Longboat Key Cheap Vacation Rental Deals

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    Travellers to Longboat Key are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    22 Matching Rentals in Longboat KeyView all 88 rentals
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    Private condo in serene setting  beach and bay1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Cute 1br condo on the water on north Longboat Key. Small one story complex with only 8 units so very private. Boat dock and kayak launch right outside and great fishing from the dock. Washer and dryer inside the unit. Easy 3-4 minute walk to the beach or easy drive to Holmes Beach and Anna Maria...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whitney Beach 145 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. Community pool. Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    About this property
    MONTHLY- FURNISHED- 2 bedroom/ 1.5 bathroom unit is ready to go! Completely turn key, with bicycles,kayak and beach chairs! Amazing heated 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house is located on Longboat Key, outside of the city of Sarasota, on the west coast of Florida. There is an airport in Sarasota, as well as in Tampa, which is a little over an hour away. Longboat Key is pretty and green, and is linked, by bridge, to Anna Maria Island on the north, and to St....
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    Longboat Key, Florida 1234
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
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    • Private Garden
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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
    • Air Conditioning
    • Waterfront
    • Porch
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Washer
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    • Waterfront
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 - WINTER RENTAL/FURNISHED - 3 month minimum - This lovely unit located in Windward Bay Association has just been purchased and is now for rent! The home is a one bedroom/bath/ - ground floor unit...totally turn key and ready for you! The new owners are putting a fresh coat of paint inside,...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    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 / 17
    (3)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2016
    We stayed at this unit for two weeks and found it an ideal place to stay overlooking the Gulf of Mexico on Longboat Key. The studio unit is cozy, but did not feel cramped with...
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    About this property
    ** OCEAN FRONT 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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    Charming, quiet, beach side cottage with garage.  Avoided  IRMA damage.1 / 13
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Housekeeping Included
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2017
    Lovely, pleasant, clean, comfortable home. The house was so well supplied. It had everything we needed. Really nice lanai with comfortable patio set where we enjoyed our coffee...
    Reviewed 6 February 2017
    Nicely decorated.Quiet, very clean, and great floor layout. Beds were perfect. The lanai is awesome.200 yards to fine beach. Internet was fast and we streamed movies on the...
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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. High speed internet and digital TV. Quiet upscale residential...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kick your shoes off, put on a pair of flip-flops, and walk down to the private bay side beach during your stay at this 2-bedroom, 2.5-bathroom vacation rental condo in Longboat Key! The condo is ideally located in the Cedars East community and has a view of the clear blue Sarasota Bay. Up to 6...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beachfront Unit 4, Cozy Getaway for two1 / 11
    (7)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 15 October 2017
    Wow! From the moment we walked in till the day we walked out, we loved this place! It was the perfect size for us and only steps to the beach right off the patio. Beach...
    Reviewed 9 March 2017
    It was so nice to walk out onto the patio, sit and enjoy a glass of wine and watch the sunset or take a few more steps right out onto the beach. There's a table with umbrella...
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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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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Pet Friendly on Longboat Key1 / 25
    (23)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Nice and clean dog friendly condo. Public beach access is directly across the road. Fabulous screened-in balcony to enjoy dinner and watch the sun set over the Gulf. Lots of...
    Reviewed 23 December 2017
    We have stayed in this owner's Siesta Key condo this past summer and enjoyed the area that we decided to come back and rent the Longboat Key Pet Friendly Condo. We brought our...
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    About this property
    ****Please go to longboatbeachcom .**** for more information. I will email you a quote from my booking program. Condo was updated July 2016, so pictures are current. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beachfront Longboat Key Studio #11 / 6
    (6)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Our second visit, stayed at this place again and will continue to do so. Everything you need is there. Always clean, right at beach and close to great places to eat. If you want...
    Reviewed 12 September 2016
    We love the place,was very clean.Had all the amenities.Loved having the beach at our doorstep.We will definitely come back.
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    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
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    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Gull is the perfect resort for complete relaxation in this lovely cottage on Longboat Key. We are offering week 37 of this timeshare. (Sept 16-23) Unit 10 is on the Bayside is fully equipped; has a four poster beds and wood burning fireplace. You won't find another resort quite like this...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, 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
    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2015
    We rented both the Luxury Log Cabin and the Tree House next door. Only complaints were in the Log Cabin - they need to put up drape/curtain in loft bedroom for those guests as...
    Reviewed 30 June 2015
    Cons:1. In the picture of the kitchen, it shows a crock pot and salt/pepper shakers. Neither were provided, so don’t plan on a crock pot meal like I did! And bring your own...
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    About this property
    Orchard is a Private Cottage. 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 Very quiet area in the North Village of Longboat Key, Fla. Enjoy other...
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit is booked until August 2018, unfortunately, there is no availability prior to August 2018 Please refer to my website (google white sands of Longboat Key, FL) for more pictures and details! Unit was renovated in 2016! This fully furnished 2 bed/2bath townhouse (bay side unit 113, refer...
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    Longboat Key, Florida 34228
    Holiday Rental House - 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
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Vacation Rental: Seaplace, a gulf-side community on south Longboat Key. This stunning turnkey furnished 2 bed, 2 bath 4th floor unit (elevator provided) provides everything you need to enjoy a beach vacation. Amazing amenities include gated entry, lush landscaping, recreational trails, on-site...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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