Oldsmar Rentals

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1,552 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

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!

Price per night from

$572

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$207

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$201

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$205

440 West Condos 808-N Beautiful Water View

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$155

Lovely Tropical Sunlit bedroom

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$228

Quiet Waterfront Home, Gulf-access

Tarpon Springs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$241

Mediterranean Lakefront Mansion

Tampa house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

Price per night from

$1,140

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

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$192

Cottage Apartment Spring Bayou

Tarpon Springs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

Price per night from

$149

Nice mobile home by the canal

St. Petersburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$95

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$275

8 houses from beach and gulf in Clearwater beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$263

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

Indian Rocks Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$516

Sandy Shores Beach House - Beachfront Home

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$626

Sea Breeze Beach House - Private Pool

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“FANTASTIC PLACE.” We had a party of 10 and we still had plenty of room for everyone. The view was awesome we watched the dolphins play from the balcony. It was a little distance to the beach but quiet and away from all the traffic. Everything was in walking distance and convenient.Melissa was there right away to take care of any problems we had. My family and I had the best vacation and we would highly recommend.

Price per night from

$658

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

Price per night from

$1,581

Westwinds Paradise - Private Pool - Steps from the sand!

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$921

Exclusive Isla Bonita - Private Pool - Steps from the sand

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$921

Art's Beach Retreat

Belleair Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$287

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$476

Key West Style Beach House

Indian Rocks Beach townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$153

One bedroom Studio Apartment

Crystal Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

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

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

Price per night from

$217

Beautiful 2 bedroom condo,mins. drive to beach, pool

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$207

Alice's Beach Bungalows Private Oasis TI, FL

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Short vacation” Still on our short vacation. So far everything is perfect! Susan has been very helpful with any questions and has been there anytime we had needed her. Hot tub is great! Place is super clean and efficient.

Price per night from

$217

Belle Harbor 404M Waterfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$207

ADVENTURE ISLAND & Busch Gardens Home

Tampa house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

“Home away from home” The home was magnificent, very spacious, very clean, the decor was awesome!!!location is great we all loved it Mr Sidney was very nice the rental process was very easy. Thank you we will rent from you again.

Responds fast! avg. 2 hours 59 minutes

Price per night from

$190

Modern Studio, Designer Kitchen Walkable Downtown

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$132

Tarpon Woods Condo with Lake View

Palm Harbor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$58

Viewing 38 of 1,552
rentals in Oldsmar

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