Guesthouses Hollywood

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395 guest houses

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Boat available

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Price per night from

$193

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Boat available

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Price per night from

$172

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Studio Vacation Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Boat available

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Price per night from

$172

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$745

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$573

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$1,775

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$487

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$1,775

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$916

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$745

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$1,145

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$687

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$745

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$745

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$745

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$745

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 29 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$630

Beautiful Large Studio Condo on the Lake

Orlando apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Boat available

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Price per night from

$228

BAYSIDE CONDO WITH BOAT

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

1 of 2 match: Rental types, Boat available

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Price per night from

$429

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Boat available

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Price per night from

$441

Weeki Wachee main river .Not a canal ,walk to Rogers park beach

Weeki Wachee house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Boat available

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Price per night from

$315

Luxury 2BR Suite at Vacation Village at Weston

Weston hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Boat available

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Price per night from

$1,144

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 21 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$1,498

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Rental types, Boat available

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Price per night from

$194

Entire Guest House- Sunset Hide A Way

Naples house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 22 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$594

4801 ML - Ideal Retreat Townhome Oasis with Pool

Kissimmee condo

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 40 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$106

1979 MD - Luxury 5BR, Private Pool, Near Disney

Four Corners condo

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 40 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$98

Renzzi Wynwood Apartments

Miami apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Boat available

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Price per night from

$229

Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks

Cortez cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 21 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$233

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 21 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$156

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 21 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$252

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 21 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$234

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$401

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 21 minutes

1 of 2 match: Rental types, Boat available

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Price per night from

$227

“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.

1 of 2 match: Rental types, Boat available

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Price per night from

$315

Sanibel Condo bike path Heated pool tennis court grill area short walk to beach

Sanibel Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Boat available

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Price per night from

$401

sunset hideaway

Davenport house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Boat available

1 of 2 filters match

Price per night from

$172

Westgate Town Center, Family Villa, 1 bed/1 sofa/Kitchenet 9min from Disney

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Rental types, Boat available

1 of 2 filters match

Price per night from

$112

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