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5,051 guest houses

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Toaster Waterfront

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Price per night from

$173

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Rental types Toaster Waterfront

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Price per night from

$230

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Tropic Terrace #9 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace #5 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace Resort #27 - Beach View Suite

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$154

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$383

Regatta Beach Club 414S '90 day min stay with 2 week lead time'

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$104

Dunedin Garden Cottage Quiet Roof Terrace | Walk to Downtown Dunedin

Dunedin bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$330

Tropic Terrace #55 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace #54 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace Resort #59 - Beach View Penthouse

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$258

Tropic Terrace #40 - Beachfront Resort

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$208

Tropic Terrace #41 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$184

Tropic Terrace #37 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$154

Tropic Terrace #15 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace #29 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$236

Tropic Terrace #35 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$154

Bay Watch #5 - Weekly Beach Rental

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$100

Tropic Terrace #44 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Toaster

2 of 3 filters match

Price per night from

$165

Tropic Terrace #49 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace #18 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$117

Tropic Terrace #32 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$166

Chateau 1E - On the Beautiful Belleair Beach

Belleair Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$160

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$1,230

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$1,420

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$127

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$953

Bay Harbor 301 Beautiful Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$1,496

440 West Condos 808-N Beautiful Water View

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$155

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$1,054

Brightwater Point 105 Grand Water Views

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect in every way!” Perfect location; beautiful condo; everything we needed. If I could have a negative comment it would be that the couch was a little uncomfortable. I can't say enough about how perfect; we have made arrangements to return!

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$1,047

Island Key Condos 303 Large Balcony overlooking Bay

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing” We were first time renters and we're very anxious. We couldn't have been more impressed. There was so much space and the condo was spotless. The area was quiet and the apartment block was spotless. The pool was heated and spa was hot. The staff in the office were so nice and helpful made us feel really valued. Will definitely be returning and would highly recommend the rental company.

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$280

Bay Harbor 501 Beautiful 5th Floor Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$888

Harborview Grande 306 Waterfront 3 Bedroom 2 Bath Condo

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$446

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$479

Brightwater Point Condo 106 Amazing Water View Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$563

Belle Harbor 509M Stunning Luxury Condo with Panoramic Water View.

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

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Price per night from

$337

440 West Condos 1404-N 14th Floor Panoramic Water Views

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Rental types, Waterfront, Toaster

2 of 3 filters match

Price per night from

$377

Viewing 38 of 5,051
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