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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$285

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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

One bedroom Studio Apartment

Crystal Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

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$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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$300

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$172

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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$161

Take a step closer to paradise! SEAGATE – Apt. 302

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Would love to return several times a year....near perfect!” The condo was beautiful, well appointed and maintained. Located on a nearly perfect beach. It appears we were the first tenants after hurricane Irma. My only complaint was the AC didn't work for the 1st half. The property manager seemed to be doing all she could to remedy the situation My only recommendation is that maintenance should probably have checked it out along with everything else after the storm. I would still highly recommend this to anyone wanting to experience a beach vacation in a great location and in a wonderful condo. The owner is great to work with also.

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$345

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$84

SUNSHINE HOLIDAY

St. Petersburg manor house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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$1,148

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$1,054

Seminole Vacation House Spacious Vacation House

Seminole house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$107

Tranquil by Belleair Beach/Largo

Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$167

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

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$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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$104

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$287

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

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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$5,200

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$1,229

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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$1,385

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,420

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$127

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$345

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

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$585

Belle Harbor 407M Luxury Clearwater Beach Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$318

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$953

440 West Condos 1501-N Condo with a water view

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$847

Bay Harbor 301 Beautiful Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$1,495

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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Price per night from

$206

Viewing 38 of 1,407
rentals in Oldsmar

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