Oldsmar Rentals

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1,407 Houses

Dolphin Bay Retreat

Oldsmar house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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$287

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$195

Florida Blue House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$183

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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$389

Great rentals within 20 miles that match your search

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$172

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$230

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$568

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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$344

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$92

440 West Condos 508-S Gulf Front Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$481

Intercoastal 209 Water View from this Charming Condo

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$5,197

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$1,228

440 West Condos 1408-N Gulf Front Condo with amazing views

Clearwater apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$179

Sunfish Flat Beachfront Condo 3 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,384

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$127

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,419

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$344

Belle Harbor 1105M Fabulous Luxury 11th Floor View at Belle Harbor

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$585

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$952

440 West Condos 1501-N Condo with a water view

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$847

Belle Harbor 407M Luxury Clearwater Beach Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$318

Bay Harbor 301 Beautiful Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$1,494

Elegant, Direct Ocean-Front Condo w180 degree view

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Just perfect!!!” I can't think of any way the condo could have been better. The view is PERFECT. Plenty of towels, blankets, kitchen items, Keurig coffee maker, toilet paper, paper towels, dishwasher detergent, beach chairs, toys, even a cooler, DVDs, games... everything was there. The only thing we couldn't find was a vase for flowers! We managed with a large water glass. We didn't use the pool so I can't comment on that. The beach was uncrowded and had fresh sand. The condo was super clean and bright. Even the exterior halls were hosed down each morning. Thank you so much Kay for a great vacation!

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$573

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$207

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$201

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$206

440 West Condos 808-N Beautiful Water View

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$155

Lovely Tropical Sunlit bedroom

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$229

Mediterranean Lakefront Mansion

Tampa house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

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$1,141

3br - Belleair beach vacation rental, 3bd/2bth

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$192

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$343

Cottage Apartment Spring Bayou

Tarpon Springs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

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$149

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$276

Beachfront 2br, 2 Bath condo-Directly on Beach! Beautiful Views Of The Gulf!

Indian Rocks Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$516

Sandy Shores Beach House - Beachfront Home

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$626

Clearwater Beach Cabana - Private Pool

Clearwater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 26

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Price per night from

$1,715

Viewing 38 of 1,407
rentals in Oldsmar

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