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Longboat Key Vacation Rentals

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    Travellers to Longboat Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 89 Rentals in Longboat Key
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    Las Hermanas/Starfish #3 Beach front Longboat Key1 / 7
    (15)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Beachfront Studio #1 Longboat Key1 / 6
    (9)Excellent
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Las Hermanas/Starfish #2 Beachfront Longboat Key1 / 7
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Beachfront Unit 4, Cozy Getaway for two1 / 11
    (13)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 June 11, 2019
    Want to get away for a week? This place is perfect if you are a beach lover. We went last week and were very happy with the recently renovated studio apartment with full...
    Reviewed May 2, 2019
    Very nice. Love the immediate access to the beach. Limited kitchen supplies, which was ok for us, but we would have loved grill utensils
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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 stay at the beach. It's a neat studio apartment with patio and sandy beach at your door. The full size galley kitchen supplies...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 2
    ZILLI VILLA1 / 25
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2019
    Best kept secret I Florida. Steps from the beach and very private. Everything you need for the perfect vacation get away. We will be back.
    Reviewed June 12, 2019
    I and my family have been vacationing at Zilli Villa on Longboat Key for 5 years and plan on returning for many more. Beautiful oceanfront 2 bedroom home directly on one of the...
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    About this property
    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
    Zilli Ocean Front 1011 / 44
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Patio
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 5, 2018
    Do you want to walk right out onto the beach ? Then this is the place you want to be. Our second year staying here. Multiple upgrades & our communication with the Zilli team...
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    About this property
    This is our newest addition and being updated from floor to ceiling literally as I type this ask for PDF to see the amazing new look . In addition see below to get a feel for our brand and where we are taking this property . It is part of the Zilli Collection each with the Zilli touch of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    225* BEACH FRONT APARTMENT *1 / 19
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Patio
    • Waterfront
    • Wi-Fi
    Suitability
    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
    ~ DIRECT BEACH - OCEAN FRONT ~ . Longboat Key - Ocean Front Condo ** SPECIAL ** August - September ~ Beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get. ~ We offer the lowest...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Charming Beach House in Longboat Key/ pool/pet/dock1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2018
    We enjoyed our stay so much at this cute, cozy house. The house has all the amenities needed and was comfortable and very clean. The neighborhood was very quiet and has private...
    Reviewed October 25, 2017
    This house is a great place for vacation. We enjoyed all amenities provided. The house is fully equiped with everthing you need. Thank you very much.
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    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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Outrigger Resort unit #31 / 18
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 2, 2018
    This 3 bedroom, 3-1/2 bathroom, 2 floor condo exudes lovely old Florida charm. Completely remodeled and very spacious, the condo is very quiet as are the beach and pool. Close...
    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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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Steps to the Sand! Longboat Key 2 Bed 2 & 1/2 Bath Gulf Front Condo with Den.1 / 28
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Sauna
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2019
    Fantastic location, the view from the lanai out to the beach is excellent, spectacular sunsets every night. The condo was very well appointed, the beds were super comfortable...
    Reviewed July 15, 2018
    Really clean, comfortable place for our family of 5...two king beds with own bathroom and a comfy pull out sofa for a young child. All matresses were temperpedic and nice...
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    About this property
    Newly Renovated in November 2016 our unit features direct gulf views from the living room, kitchen and master bedroom. Brand new appliances and fixtures throughout including in unit washer and dryer. Each bedroom has a flat screen TV, king size bed and an on-suite bathroom. The den has a queen...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Renovated Beachfront Condo with Spectacular Ocean View unit 4031 / 28
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 13, 2018
    My wife and I headed to the beach to get away from it all. Her one requirement was a view of the water from our room. This condo definitely had that. It was wonderful to watch...
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    About this property
    Welcome to Paradise! View! View! View! A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit 403. Whether you want a relaxing visit enjoying the relaxation of all of the comforts of home with stunning views of...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
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    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Family friendly townhouse condominium with wonderful amenities all around! Cedars East Tennis Resort Just updated for your vacation comfort! -2 BR, 2.5 Bath – 1440 square feet -Partial Bay views out of Kitchen and 2nd bedroom windows -King sized bed in master with huge closet, two sinks and...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
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    • Washer
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can’t get closer to a private beach without the beach front price tag! Longboat has monthly rentals but will rent for less , and block the time , please contact us !! This remodeled, spacious bungalow is nestled in a waterfront community on Longboat Key, just minutes to the beach. From a...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for beachfront paradise ? It doesn't get better than Club Longboat . This spacious condo comfortably sleeps 6 within 3 separate bedrooms. With wide sliding doors off the master and living area, amazing sunsets color the room and invite you to the beach. Relax or dine on the over sized...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for beachfront paradise ? It doesn't get better than Club Longboat . This spacious condo comfortably sleeps 6 within 2 separate bedrooms and a queen pullout sofa. This newly remodeled condo is beautifully updated with coastal feel , including a new kitchen with white cabinetry, Quartz...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Life on the island doesn't get better than this ! This spacious recently renovated condo on beautiful Longboat Key is uniquely situated steps between the spectacular crystalline beach and the expansive active bay ! In the morning watch the sunrise and the boats head out from the bay side as you...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    ~ The Beach on Longboat Key ~ * OCEAN FRONT DLX STUDIO  *1 / 28
    (4)Very good
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Patio
    • Cable/satellite TV
    Suitability
    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
    ~ BEACH FRONT DLX STUDIO ~ * This complex is a two story building with only 14 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 you see is what you get, direct beautiful Ocean views.The...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bathroom, Sleeps 3
    Zilli Tower 5031 / 23
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Parking
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The Condo was well equipped for cooking,relaxing,and just having a terrific vacation. easy access to beach,pool and other amenities. Shopping and restaurants very short drives...
    Reviewed May 14, 2019
    We have stayed there twice and going back for 3rd and 4th times next year. Condo is lovely , beach is terrific and quiet. Owners are super to work with. Can't miss. Jim Peterson
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    About this property
    Zilli Tower 503 is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection . Each with the Zilli touch of amazing view, decor, ( not typical wicker furniture , silly beach artifacts 40 year old flooring etc 1 SIZE fit all .) We...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Housekeeping Included
    • Wi-Fi
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ~STUDIO APARTMENT - DIRECT BEACH FRONT ~ ~ Beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get. ~ We offer the lowest rates in this resort compared to all the other units and we...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious multi-level 4 bed/3 bath home w/elevator just a short walk to the beach with private deep water dock! If you are looking for a spacious home that provides a sense of being in an exclusive gated community, is very quiet and tranquil and has access to one of the most beautiful beaches in...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Away to Paradise! Unit 301 with 180 degrees unobstructed Mexican Gulf View. Beachfront condos on Florida's gulf coast. This is a corner condo so you have a more space and side window view. A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Beach front condo in Longboat Key1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Housekeeping Included
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautiful, newly renovated Gulf-front sunny unit with vaulted ceilings and spectacular views. The open floor plan of living room, dining room, kitchen and den offer full views of the sparkling turquoise water, blue sky and white sandy beach. Newly renovated with beautiful wood floors...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Castle in the Sky Near Beach and Tennis1 / 13
    (57)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Hot Tub
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    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2017
    We stayed in this lovely home in Holmes Beach for a month with another couple. It was immaculately clean and beautifully appointed. Furnishings were tastefully selected with a...
    Reviewed January 22, 2017
    Home was clean and spacious, kitchen was well-equipped, kids had their own room and the resort was close to restaurants and the beach AND the weather in January was awesome...
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    About this property
    ++++++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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Sauna
    • Washer
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    • Ocean Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing totally furnished 5 Star beech front time share rental Property with PARTIAL ocean view. 2-bedrooms and 2-baths. Sleeps six comfortably: king size bed, two twin beds, and queen size sleep sofa. Wonderful free amenities. Check things out on line by looking up the Veranda Beach Club for...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Balcony
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    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit is a two bedroom condo available for rent during April 11-18, 2020 (Saturday...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Find your tropical oasis in sought after LONGBOAT KEY. Wake to sunrises over your dock overlooking Sarasota Bay and catch the sunset sinking into the Gulf of Mexico-. Enjoy Serenity in this lovely home, or By Bike or Car Minutes to St. Armands' Circle or jump into your Boat; down the Deep Water...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1/1 $165 DIRECTLY ON THE BEACH(SEPT. OPENINGS 4 OR MORE NIGHTS)1 / 24
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed July 21, 2018
    We absolutely loved Kim’s condo. The location was outstanding and the condo was beautiful. We loved everything about being here. Nothing like waking up and sitting on balcony...
    Reviewed May 12, 2018
    Booked this resort because of all the great reviews it gets,and the reviews were right!A very relaxing atmosphere,our 1 bedroom condo was clean,well equipped and spacious on the...
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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. Contact owner before booking. If you need dates that are not open or a...
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    Location Information
    Longboat Key, Florida 33312
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Beautiful, spacious 2/2 condo on Longboat Key available immediately! 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, tennis,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
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    • Terrace
    • Private Garden
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    About this property
    Savor warm Gulf breezes while resting lavishly in this full unobstructed Gulf-front view upscale condominium complex located directly on the Gulf of Mexico providing SPECTACULAR VIEWS AND BREATH TAKING SUNSETS !! New designs were created using South Beach style with a twist of rustic and...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Beautiful two story condo with views of the Gulf of Mexico. This condo includes a dining room, full kitchen, deck overlooking the Gulf of Mexico, housekeeping, free breakfast every Monday morning. The feeling of a private beach home with the benefits of a condo, including full access to a pool, hot...
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    Longboat Key, Florida 34228
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Beachfront Condo, 1 Bedroom + Other (See Description), 1 Bath, (Sleeps 2-4) This condo is REALLY right on the beach. The large balcony is 'punched out' from the building providing an unobstructed view of both up and down the beach for miles, unlike virtually all other condos on the Key. (No screen,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Longboat Key Bayfront condo in Bay Isles1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 12 is a two bedroom condo available for rent 4-13 thru 4-20 2019 (Saturday to...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    1400 sq ft free standing villa Our villa has 2 bedrooms, 2 bathrooms, living/ dining room, full kitchen and two bonus rooms. It is located on the bay which comes into the center of the community and features a marina - manatees and dolphins have been known to stop by! .Our unit is close to the...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    GULF FRONT - ON THE SAND SPECTACULAR GULF VIEWS AND SUNSET VISTAS Watch dolphins and gorgeous sunsets from your private covered balcony of this spacious condo on beautiful Longboat Key FL. Miles of unobstructed 180 degree views from all rooms. Fourth floor (of 5) corner unit. Elevator. Whether...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    The spectacular view of Sarasota Bay is magnificent during the day and in the evening the skyline lights of Bradenton and Sarasota are on full display. Thus, every room has water views that provide a sense of beauty and tranquility. This bay to gulf property is a 4 minute walk to beach. This unit...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Stunning, newly renovated 3BR/3BTH home on preferred southern end of Longboat Key. Luxury interior design features cozy, oversized Restoration Hardware furniture, high-end linens, fully appointed gourmet kitchen, large master bath with Jacuzzi overlooking canal, and more. Whether it's a fun day a...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 10 is a one bedroom condo available for rent during week 14 April 6 - 13...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Little Gull Cottages is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 13 is a two bedroom condo available for rent during week 12 (Saturday...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Smoking allowed
    About this property
    This is a spacious house, located in Halyard Lane on Longboat Key, close to St. Armands Circle (3 miles) and private beach (0.5 miles). With 3 bedrooms, 2 bathrooms, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is...
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
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    About this property
    Lovely 2 bedroom/2 bath first floor Gulf front condo community with half a mile of beach! walk-out with screened in lanai and lush garden views. Just steps away from the beach, tennis courts, and two pools. Fully furnished with 3 flat screen TV’s, WiFi and cable. Master bedroom with king size bed...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Kick your shoes off, put on a pair of flip-flops, and walk down to the sparkling bay 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. Up to 8 guests can spend days at the beach, swimming in the...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 11 is a one bedroom condo available for rent during 3-23 thru 3-30 and 4-13...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Cozy ,well furnished and appointed, 1 bedroom condo on Sarasota Bay.Longboat Harbour is a gated community situated mid island,which has 4 pools, beach house, gym, games room, library, boat launch, shuffleboard,tennis court, seawall walking paths,BBQ, and is directly across the road from 10 miles of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1
    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 vacations 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.

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