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2,195 guest houses

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Rental types Waterfront Secure parking

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Price per night from

$172

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Rental types Waterfront Secure parking

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Price per night from

$230

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Nice mobile home by the canal

St. Petersburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$96

Condo on the Key

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$207

*** Isla Del Sol Paradise ***

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$172

Surfside Villas - steps from the beach

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Amazing” Absolutely beautiful! Condo is great and the area is phenomenal, Tom is the perfect host! Definitely coming back

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$258

Casa Del Sol Tampa Luxury Condo at Sailport

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$229

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$178

Luxury Romantic Oceanfront Siesta Beach Condo #304

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“What a View!” This is a very nicely decorated 1 bedroom and bath on Siesta Key Beach. You have an unobstructed view of the beach the minute you look into the condo. There's a great view from the bedroom as well! Very easy walk fo the beach..chairs and umbrella provided as well as all the amenities of home. We'd stay here again!

2 of 3 match: Rental types, Waterfront, Secure parking

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$184

Luxury water views condo in a resort style complex with lots of amenities

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Excellent Holiday Getaway!” My husband and I stayed at this beautiful condo for a week in October 2013 and it was absolutely beautiful. It was exactly what we were looking for. Beautiful birds to see right at your door step. This luxury condo is very close to downtown which was good for night life and great food. I would recommend this condo to anyone. Also the owner Sabina was very welcoming which made us feel as if we were right at home!

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$201

Comfort, Peace and Privacy (Whole House)

Groveland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$138

Waterfront Breeze Condo - Waterfront with a pool!

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$593

Clearwater Beach Furnished Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$172

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$803

Wonderful Belleair Beach Condo

Belleair Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$144

Sunsets, Cocktails and Memories!

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Spacious and beautiful” My girlfriends and I just finished our stay for the third year in a row. This is an outstanding condo. With four or five of us, there is plenty of room. The private spiral staircase to the beach is great! No waiting for the elevator with everyone else. We love sitting on the porch early in the morning and again at sunset. Spectacular views! Also you can visit the Suncoast Seabird Sanctuary which is about 1/2 block to the south. Would highly recommend this condo. We hope to be back again next year.

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$382

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$246

BEAUTY ON THE BEACH! Crescent Arms 601S FULL FRONT VIEW

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$314

Fabulous 3B Condo Bahama Bay Resort

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Loved it!” It was perfect accommodations for our family. We loved the resort. Also being from the Bahamas we loved the theme of the resort.

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$230

Fabulous 3B Condo Bahama Bay Resort 10 min Disney

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$230

Florida Waterfront Seasonal Rental

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$144

Casa Del Mar in Apollo Beach

Apollo Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$1,032

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

Ruskin lodge

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$207

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$84

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$206

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$92

“If I had only one word to describe this house, it would be Zen.” My husband & I stayed here with my three teenagers (13, 16 &' 18) over spring break. Paul answered my emails immediately when I had a few questions prior to our arrival. There was a manual that covered everything you could possibly need to know about the appliances, pool, local attractions, etc. . The home was beautiful, spotless, well-equipped and peaceful. There was plenty of space for everyone to have his/her own room. I liked that the kids could share the upstairs bath and we had our own master suite. It was easy to cook meals because everything you could possibly need to prepare them is there. The Publix grocery store is minutes away. The kids loved the pool and we enjoyed sitting outside in the evening. Getting around is simple and nothing we wanted to do was very far. Even getting to Clearwater Beach only took about 40 minutes (in heavy spring break traffic). I would not hesitate to stay here again.

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$287

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$688

Spacious clean quiet home facing the Boca Ciega Bay in Isla del Sol

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$167

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$192

Luxury Florida Villa - Waterfront with Private Pool

Crystal Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$989

Charming Lake Front Apartmeant near Disney and Attractions

Clermont apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$98

FS223236 - Champions Gate Resort - 8 Bed 5 Baths Villa

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$533

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$278

Luxury and Spacious Waterside Getaway Walking Distance to Everything

Clearwater townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$803

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$161

Tampa TreeHouse

Tampa house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Perfect Vacation Home!” This is the perfect vacation rental!! Clean, comfortable and well furnished. Close to beaches, entertainment and dining. The owner has all the bases covered and goes the extra mile to help with anything you need. I highly recommend this property for your vaction and am already planning our 2015 stay! Thanks again Javier!

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$423

A Lakeside Luxury

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Outstanding Villa in a beautiful surroundings.” We are a family of 5, stayed at the this Lakeside Luxury Villa for 9 weeks total. The house is so beautiful with all that is needed when staying with kids. Very spacious house and lots of things to do, table tennis, soccer game and Playstation game console where everybody can play. Giant TV with hundreds of satelite tv-channels. The pool area is simply fantastic, big south facing screen and large pool - sitting out there and watch the sunset is so lovely. We have rented lots of houes before in Florid and this is simply the best one we have rented. The house is close to supermarkets, mall, Disney and all kinds of activities and shopping. Do spare the words: This house is beautiful, with outstanding surroundings. Grade: 10 out of 10. Best Wishes for great stays. Stefan

2 of 3 match: Rental types, Waterfront, Secure parking

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Price per night from

$308

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