Villas Hollywood

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2,471 villas

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

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Price per night from

$510

Beautiful 2 Bedroom Condo on the Lake

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

River Island - North - East - West Villages at Orange Lake

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$246

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Beautiful Barrier Island Beach House with Pool, Spa and Dock - Walk 2 Beach!

Don Pedro Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$597

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$860

VIP island vacation home

Grant-Valkaria house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$431

Private Pool Home, SPECTACULAR Sunsets And Only Steps from the Beaches

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,148

Endless Summer - North Captiva Island 3 Bedroom 2.5 Bath, Sleeps 10 - Boat slip

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$573

Beautiful Large Studio Condo on the Lake

Orlando apartment

  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Bahia Beach Resort Little Harbor-Tampa, FL

Tampa studio

  • Studio
  • 1 bathroom
  • sleeps 4

“Perfect Vacation Relaxation Spot” The view from the room and balcony was gorgeous. Sitting on the balcony each morning sipping my coffee was heavenly. All of the amenities were close to the room and just short walks away. The property itself was well maintained and quiet while still being family friendly. The room was comfortable and a great home base at the end of our daily jaunts. Tampa, St. Petersburg, and Clearwater were very easy drives from the Inn. I can't wait to visit again.

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Price per night from

$138

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 42 minutes

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Price per night from

$1,377

Cottage By The Water With Boat Dock

Tarpon Springs cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

“Awesome-perfect in every way” We cannot say enough possitive things about this home and the hosts. We have come to Tarpon for 30 years but this is the first time we ve used flipkey and we will only use flipkey from now on. From the welcoming hug to the perfect ammenities throughout, you could not beat this offering. Location is beautiful and perfect to access anything. The hosts were so nice and they had paid attention to so many details, we were overwhelmed. They had lots of suggestions and a great notebook filled with menus and things to do. Plus hints on specials, fishing and the area. As we ended our trip they even greeted us with a weather report--there was a storm headed our way. Thank you both for making sure this was the best time we ve ever had in this, our favorite, Florida location.

Responds fast! avg. 45 minutes

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Price per night from

$138

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$1,148

Stella Maris-Beachfront, Ultimate Privacy, Spectacular Shelling, Sunset Views!

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$975

Lattitude Adjustment- Private Beachfront Home with Fishing Dock, Sunrises

North Captiva Island house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$916

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$744

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

Old Palm Waterfront Vacation Rental Home

Sebastian house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Wonderful house in great location” What a wonderful, well equipped home in such a great location. Both in the house and surroundings there is so much room to sit, walk, run and explore! All our family met here, 3 couples and 17 month twin boys and it was ideal! The porch at the back was just perfect for everyone, a wonderful safe area for the boys to play and comfortable chairs for us all to relax without a mosquito in sight! Open living room and kitchen was easy to work in with a delightful dining room where we could eat in the evenings. Good size bedrooms and bathrooms, the master suite is incredible and huge! The house is very easy to baby proof also, we took a couple of extra safety gates to keep our little guys from getting into mischief! And I have to mention the peacocks, they just stroll around everywhere, surprised us once or twice, but are very friendly and amazing birds. The location is great, there is a huge Publix , Dunkin Donuts and plenty other stores close by. I think if you want a peaceful, relaxing weekend, week or long vacation this is the home to rent. Bill Clark, the owner, was there to meet us and show us round and was on hand if we had any questions. We really look forward to going back soon!

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Price per night from

$372

Treehouse Old Homosassa/River Safaris (waterfront)

Homosassa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$258

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$488

Responds fast! avg. 30 minutes

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$114

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

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Price per night from

$273

EIKO BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK

Treasure Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

“Water, water everywhere” So very, very close to the beach. Very helpful agent. Had 11 people with plenty of room .awesome time.

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Price per night from

$688

Luxury Beach Front Villa with Pool, Captiva Island

Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Sunset Dreams - Tropical Paradise” What a wonderful place! We just returned and we miss it very much already. As my wife puts it, "it was like being in another world!" She's become an overnight ornithologist and marine biologist. The owners went well above the standard of what a normal property rental would be. From furnishings, to decor, to kitchen utensils, and appliances; they blow every rental property we've ever seen right out of the water. The home is immaculate. And the island itself has endless things to do. We've already booked for next year!

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Price per night from

$644

Island Beach cottage rental w/king+2bikes+smartTV

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$224

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

St. Pete Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$334

Amazing Condo at the Naples Bay Resort Cottages

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$320

Tropical Bliss: Lazy River, 5 Pools, Bar, 2 Restaurants, Cabanas!

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$458

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$148

Luxury 5 Bedroom Modern Home with heated pool

Coral Gables villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$2,065

Beach Dreams " Sweet Dreams Villa"

Anna Maria Island villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$515

Weekly 2 bedroom Apartment for 8 guest all amenities included

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 17 minutes

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Price per night from

$121

“Great place, good value!” This was our first time renting a house from an owner. We had a great experience. The owner Mary was very helpful and she even called us right after we checked-in to make sure that everything met our standards and we had what we needed. The unit is very clean, quiet and had everything we needed for our stay. The resort is in a great location and has easy access to expressway I-4 and 417. It takes less than 10 minutes to get to Disney and the Espn World Sport Center. We also enjoyed walking around Old Town in the evenings. We really enjoyed our stay in this unit. Thank you Mary for letting us stay there.

Responds fast! avg. 3 hours 31 minutes

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Price per night from

$109

Immaculate Spacious Villa

Orlando villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$218

Valencia

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$184

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Price per night from

$115

Bianco Sands - 1 Bedroom 1 Bath: By Beachside Management

Siesta Key villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$251

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$274

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