Oldsmar Rentals

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1,558 Houses

Dolphin Bay Retreat

Oldsmar house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$287

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$195

Florida Blue House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$182

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$286

Price per night from

$327

La Rustic House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$389

Great rentals within 20 miles that match your search

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.

Price per night from

$161

TAMPA BAY WATERFRONT CONDO!

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$171

Charming Fully Furnished 3 Bedroom Townhouse

Clearwater townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$194

Water view Bayfront 300 yards from Beach

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$295

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

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.

Price per night from

$103

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$287

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$368

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

Price per night from

$344

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

Price per night from

$480

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$1,227

Intercoastal 209 Water View from this Charming Condo

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$5,190

Mandalay Beach Club 603-P Beachfront Condo - One Month Minimum

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$355

Regatta Beach Club C1009 '90 day min stay with 2 week lead time'

Clearwater apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$118

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

Clearwater apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 50 minutes

Price per night from

$179

Sunfish Flat Beachfront Condo 3 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$1,382

Dunedin Garden Cottage Quiet Roof Terrace | Walk to Downtown Dunedin

Dunedin bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$329

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$1,417

440 West Condos 1508-S Walk to the Beach

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 50 minutes

Price per night from

$117

Bay Harbor 302 Radiant Water View of the Bay

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Great location, great condo, great price!” My family loved staying at bay harbor 302! The location was perfect, only a short 3-4 min walk to the pristine beaches. The condo was impeccable and much bigger than the pictures suggest. I cooked a lot of meals there and never did I lack anything I needed. The cooking skillets could have used an upgrade but they did the job. The bathrooms and kitchen were very up to date and clean. The bedrooms were a great size. The view from the balcony was wonderful and there was always a breeze when enjoying morning coffee or after dinner drinks. There were so many amazing restaurants within walking distance as well as great "touristy" shops. The reserved parking was great and we felt secure with having a gate at the entrance which required a code, The lobby door requiring a code, and a code for our condo door. Clearwater Beach Rentals were very accommodating and when we asked if we could check in a few hours early they made it happen. Everyone was very kind and we definitely plan on booking through them again. All in all our stay was wonderful!

Responds fast! avg. 50 minutes

Price per night from

$221

440 West Condos 1108-S Beautiful Water Views

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$124

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$126

Villas of Clearwater Beach 8A Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$219

Ocean Sands 504 Beachfront Studio Condo

Madeira Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

Price per night from

$131

440 West Condos 905-S View of Gulf of Mexico From Every Room

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$124

440 West Condos 1507-S Gulf Front Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$100

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$344

Regatta Beach Club 403N '90 day min stay with 2 week lead time'

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

Price per night from

$87

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

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$584

Viewing 38 of 1,558
rentals in Oldsmar

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