Guesthouses Tampa

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1,436 guest houses

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Boat available Waterfront

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Price per night from

$173

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Beachcomber Beach Casita | Steps to The Sand

Clearwater studio

  • Studio
  • 1 bathroom
  • sleeps 2

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$110

Unit #102 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$342

Unit #113 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$278

Unit #110 Sand Cay Beach Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$278

Unit #211 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$278

180° Waterfront Indian Rocks Beach Home- Boat & Dog Friendly- Dreamy Views!!

Indian Rocks Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$235

Family Favorite Sea Isles- Indian Rocks Beachfront and Sunsets Galore!!

Indian Rocks Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$232

XL Family Sized Beachfront on Redington Beach! Huge Pool and Hot Tub!

North Redington Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$307

Unit #103 Sand Cay Beach Resort Gulf Front

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$342

Top Floor- 5 Star - Indian Rocks Beachfront Fan Favorite!!

Indian Rocks Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$279

Sugar Sand Sanctuary - Beach Condominium

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$134

Beachcomber Beach House | Steps to The Sand

Clearwater house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful Vacation Stay!” I was a bit nervous to go online and book a vacation home, worrying it would not be as pictured or described but I was extremely happy with the beach house and the wonderful service from Belloise Realty! We had an amazing family vacation and the house was so nice and clean and was just as pictured on the site. We will defiantly use Belloise again in the future as well as request this specif house when visiting Clearwater again!

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$189

*1979 Windsor at Westide - Amazing 5bd Villa

Four Corners condo

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 40 minutes

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$148

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$195

Sarasota Waterfront and Marina Community with Tikki Bar and Grill

North Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$102

Unforgetable Waterfront Cottage Retreat

Hudson cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

“Great place to stay!” I often stay in vacation rentals for family visits, and this place in Hudson Florida was perfect. Pet birds on the fantastic dock; awesome TV; washer and dryer! When they say it has everything -- they mean it!! Thank you!

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$202

35 Steps to the Sea at Runaway Bay 112

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$132

Waterfront Island Pool Home with Hot Tub and Canoe!!

Tarpon Springs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$317

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$345

Welcome to Olympus - Fishermans Paradise - 2BR/1BA

Ruskin lodge

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$207

52 Foot Ocean Oasis Houseboat Clearwater Beach

Clearwater boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$310

Waterfront Paradise in Destination Hudson, FL

Hudson house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$179

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, Waterfront, Boat available

2 of 3 filters match

Price per night from

$138

Watch the sunset every night over the Gulf of Mexico

New Port Richey condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$146

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

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Price per night from

$181

PRIVATE BEACH OPEN** Beachfront bungalow 4BR *Htd POOL*Pet

Indian Shores house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“A wonderful place to be!” Our rental was right on the pool/beach. It was perfect! Gorgeous pool and the beach - beautiful, private - everything you could want. The cottages were spacious, clean and kitschy. They had everything you needed. You could tell good people stayed there as everything was well kept and stocked. The owner, Liz, was lovely and even though we had no pets, every pup there was well behaved and everyone was respectful of the rules. The people staying at the other cottages were wonderful and had stayed there before. Obviously Liz knows what she’s doing . My parents also stayed with us and both of them loved the place. The beds were very comfortable which doesn’t always happen in rentals. Hoping to see you next year! Cheers!

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$489

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.

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$138

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$437

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 26 minutes

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$1,380

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$158

West Village Condo, Family-Friendly Orange Lake Resort!

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$353

West Village Condo, Family-Friendly Orange Lake Resort!

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$287

West Village Condo, Family-Friendly Orange Lake Resort!

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$221

Fabulous Beach House 3BR, SPACIOUS, Beach breezes!

Indian Shores house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$430

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$489

Palm Harbor Waterfront, Game room, Kayaks and more

Palm Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$458

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

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Boat available

2 of 3 filters match

Price per night from

$744

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