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1,370 Houses

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Dolphin Bay Retreat

Oldsmar house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$287

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$195

Florida Blue House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$182

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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$286

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$327

La Rustic House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$389

Great rentals within 20 miles that match your search

One bedroom Studio Apartment

Crystal Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

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Price per night from

$115

Beachfront GULF Cottage at beautiful Sandy Shores on Gulf of Mexico

Indian Rocks Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$299

Beachfront GARDEN Cottage at beautiful Sandy Shores on Gulf of Mexico

Indian Rocks Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$217

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

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Price per night from

$161

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

REDUCED FOR APRIL!

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

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Price per night from

$171

Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$344

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. 36 minutes

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Price per night from

$138

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$218

Relaxation at the Tropical Pool House

Tampa house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$446

One Of The Last One Story Beach Houses

Indian Shores house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$328

Historic Old Northeast Coastal Decorated 1 Bedroom

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$144

Sunny Side Pavilion at the Avalon

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$95

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$84

SUNSHINE HOLIDAY

St. Petersburg manor house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$1,145

Beach condo

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$745

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

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Price per night from

$1,052

Seminole Vacation House Spacious Vacation House

Seminole house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 50 minutes

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Price per night from

$107

Tranquil by Belleair Beach/Largo

Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$166

PET-FRIENDLY, BEACH RENTALS IN PARADISE A

Indian Rocks Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Excellent!” We really enjoyed our stay in this clean, welcoming, homey, family-friendly vacation home. The owner was very sweet and greeted us personally when we arrived. We were close to a quiet sandy public beach and in a super location to explore many other fun spots. There is an excellent Thai restaurant within walking distance. There are beautiful views from the balconies, particularly when a thunderstorm is coming. Couldn't ask for anything more.

Responds fast! avg. 2 hours 43 minutes

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Price per night from

$229

TAMPA BAY WATERFRONT CONDO!

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

Charming Fully Furnished 3 Bedroom Townhouse

Clearwater townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$194

Water view Bayfront 300 yards from Beach

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$295

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

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Price per night from

$153

1BR Pool View Condo in Clearwater Florida

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Outstanding as usual.” Second year staying at the Avalon. Great location! About 5 miles to the beach one way, and about 6.5 the other way. Everything needed is within walking distance. Pool is great if the beach isn't your thing. Excellent workout room.

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Price per night from

$103

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$368

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$229

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$567

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$92

440 West Condos 508-S Gulf Front Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$480

Viewing 38 of 1,370
rentals in Oldsmar

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