Oldsmar Rentals

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244 Houses

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$195

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$286

Great rentals within 20 miles that match your search

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$229

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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Price per night from

$92

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$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

$205

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$343

Cottage Apartment Spring Bayou

Tarpon Springs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

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Price per night from

$149

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$275

8 houses from beach and gulf in Clearwater beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$263

Sandy Shores Beach House - Beachfront Home

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$626

Exclusive Aqua Escape - Beachfront with a pool!

Indian Rocks Beach house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$2,172

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.

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Price per night from

$658

Coconut Beach House - Private Pool

Clearwater house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$824

Beach Paradise Beach House - Private Pool

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$2,634

Clearwater Beach Cabana - Private Pool

Clearwater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 26

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Price per night from

$1,712

Luxury Florida Villa - Waterfront with Private Pool

Crystal Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$987

Exclusive Isla Bonita - Private Pool - Steps from the sand

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$921

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$476

Key West Style Beach House

Indian Rocks Beach townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$153

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

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Price per night from

$190

Indian Shores beach front complex

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$137

Modern Studio, Designer Kitchen Walkable Downtown

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$132

Tarpon Woods Condo with Lake View

Palm Harbor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$58

Beach front condo on Redington Shores

Redington Shores condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$134

Swedish owned Spacious Condo with view over beach

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$264

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

1 Bedroom Madeira Beach Cottage

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$155

Alice's Beach Bungalows 2 bedroom

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A perfect spot for us and for our golden retriever!” What a great place to enjoy the beauty of Treasure Island. The bungalow that we stayed in was wonderful...clean, a well stocked kitchen, beach towels, a great backyard. Susan, the owner, was also great to work with on every level. She was attentive, often checking in on us to make sure all was going great with our stay. She was also responsive to our rental needs and responded immediately if we had a question, etc.. She also embraced our golden retriever and he, too, immediately became fast friends with Susan. This bungalow is literally a block from the beach, a short walk over the bridge to John's Pass and close to grocery shopping, lots of great restaurants right on the beach, etc.. A great experience and we will definitely plan to stay at this bungalow again!

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Price per night from

$315

Paradise Golf Beach apt close to Downtown Clearwater (Florida Dream)_

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$160

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$228

X Alice's Beach Bungalows 2 bdrm 500' to Beach!

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$373

Florida Waterfront Seasonal Rental

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$144

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

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

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

Viewing 38 of 244
rentals in Oldsmar

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