Villas Old Town

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3,287 villas

Big Bamboo is a magical adventure on an out-island tropical paradise!

Andros villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Boat available Smoking allowed

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Price per night from

$1,090

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Clothing Optional 420 Glamping Yurt for Couples with AC and Heat

Seville tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$114

Waterfront Fishing Dock HotTub FirePit Pond Deck C

Hanahan house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$253

“Perfect” Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back.

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$316

Water Street Carriage House

St. Augustine cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$217

The Tipsy Turtle Direct Oceanfront

Palm Coast house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 40 minutes

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$458

Seahorse Oceanfront with Balcony Sleeps 6 Kitchenette

Daytona Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 40 minutes

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$295

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$189

Responds fast! avg. 3 hours 34 minutes

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$1,606

❤️ The Funky Pelican Direct Oceanfront Retreat

Palm Coast house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 40 minutes

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$458

Saint Johns riverview

Astor apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$167

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$263

AWESOME INTRACOASTAL w/ BOAT DOCK and HEATED POOL

North Palm Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 3 hours 59 minutes

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$213

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$246

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$689

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

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$138

Private Island Rental with 19' Boat, Seabird Key

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Heaven On Earth!” From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from an outstanding outdoor kitchen, complete with state of the art grill, oven and microwave along with dinnerware, glassware etc. Not to mention the kitchen inside the house comes complete with all you need also. Even spices, just not food! The house itself is amazing and has a awesome stereo system so you can have music in the house, on the decks and on then beach! You can snorkel, swim, fish, sail, canoe, kayak, go tubing walk along the perfectely maintained tropical paths. From sunrise to sunset you day will be filled with beautiful scenerey, The view from the front porch is my favorite, I could sit there all day and have! This was our 7th trip and we had a extended stay of 10 glorious days, also our first trip with friends who loved it as much as we do! We've spent my birthday and our anniversary (back to back) here many of times and there is no place else we would rather be! The island is alive with hermit and land craps and Iguanna's and birds of all sorts. It's so funny to see a hermit crap go by with some sort of object he found as a shell. At night when you turn all the outside lights on it's like a magical transformantion! I can not say enough good things about Seabird Key. The owners and care takers do such a amazing job! Thank you for sharing this tropical paradise with us and we hope to be back again soon!

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$2,003

Paradise Creek Cottages with Van.

Andros Town cottage

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$458

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$158

The One Love Waterfront King Suite Clothing Optional 420 Friendly

Seville house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$143

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$201

Villa Westgate Lakes Resorts

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$167

Weekly 2 bedroom Apartment for 8 guest all amenities included

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 17 minutes

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$121

Westgate Lakes Resorts

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Boat available, Smoking allowed

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Price per night from

$224

Studio Vacation Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Smoking allowed, Rental types, Boat available

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Price per night from

$172

Gulf to Golf Tropical Cottage Villa

Naples villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Rental types, Smoking allowed

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Price per night from

$172

VillaDelSol:6Bedroom4Bath HeatedPoolHome

Davie villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$590

HGTV - The Blue Villa - Rewarded Luxury Clearwater

Clearwater villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 53 minutes

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$457

322 Ocean One

Hilton Head villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$210

2386 Lighthouse Tennis - 2 Bedroom near Harbour Town and Sea Pines Center

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Rental types, Smoking allowed

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Price per night from

$145

Renovated Villa, Lagoon & Golf Course Views, Onsite Pool/Tennis

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Rental types, Smoking allowed

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Price per night from

$120

“Great Vacation Experience” We loved pretty much everything. Beautiful island, nice and ample villa with appropriate equipment, great location directly at the lagoon - alligator included. Wonderful beach just a five minute walk away. We will always remember this amazing vacation experience!

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$165

2376 Lighthouse Tennis - Pet Friendly Villa, near Sea Pines Center

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$165

Oceanfront Palmetto Dunes Villa, 65 Ocean Lane-106 Windsor Place

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Rental types, Smoking allowed

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Price per night from

$195

490 Captain's Cove, 3 Bedroom PD Townhouse, 10/1/2022 Completed Renovation

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$295

6 Sailmaster Commons - 2 Bedroom Shipyard Condo

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$150

2115 Seacrest- Oceanfront Complex, Steps to the Sand

Hilton Head villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$220

123 Forest Beach Villas - 3 Bedroom Condo

Hilton Head villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$180

Viewing 38 of 3,287
rentals in Old Town

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