Oldsmar Rentals

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1,070 Houses

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$195

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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$286

Great rentals within 20 miles that match your search

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

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$230

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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$345

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

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$1,230

Intercoastal 209 Water View from this Charming Condo

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$5,201

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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$1,386

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,420

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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$586

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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$1,496

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

Mediterranean Lakefront Mansion

Tampa house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

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$1,142

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

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$192

Nice mobile home by the canal

St. Petersburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$96

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$276

8 houses from beach and gulf in Clearwater beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$263

Sandy Shores Beach House - Beachfront Home

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$627

Coconut Beach House - Private Pool

Clearwater house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$826

Sunshine's Hideaway - Beachfront with Private Pool

Indian Rocks Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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$1,450

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

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$1,584

Exclusive Isla Bonita - Private Pool - Steps from the sand

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$923

Art's Beach Retreat

Belleair Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$287

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$402

Key West Style Beach House

Indian Rocks Beach townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$153

“If I had only one word to describe this house, it would be Zen.” My husband & I stayed here with my three teenagers (13, 16 &' 18) over spring break. Paul answered my emails immediately when I had a few questions prior to our arrival. There was a manual that covered everything you could possibly need to know about the appliances, pool, local attractions, etc. . The home was beautiful, spotless, well-equipped and peaceful. There was plenty of space for everyone to have his/her own room. I liked that the kids could share the upstairs bath and we had our own master suite. It was easy to cook meals because everything you could possibly need to prepare them is there. The Publix grocery store is minutes away. The kids loved the pool and we enjoyed sitting outside in the evening. Getting around is simple and nothing we wanted to do was very far. Even getting to Clearwater Beach only took about 40 minutes (in heavy spring break traffic). I would not hesitate to stay here again.

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$287

3 bedroom, 2 bath home, just steps to the beach

Treasure Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“What a great week we had” We recently had a family reunion at this beach house. There were eight of us and there was plenty of room. The house was a wonderful place and we really enjoyed morning coffee around the island in the kitchen and s'mores in the evening on the back deck around the fire pit. Several times we grabbed a glass of wine and walked to the beach to watch the sunset and even saw a few dolphins. The area seemed to have a lot of events happening nearby, sand sculptures on the beach, shopping at a restored fishing village with several unique shops, bands on the sands and fireworks. The oversized wrap around deck added extra room to what already felt like a spacious house. The house is beautiful and we look forward to vacationing there again.

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$459

Tampa TreeHouse

Tampa house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Perfect Vacation Home!” This is the perfect vacation rental!! Clean, comfortable and well furnished. Close to beaches, entertainment and dining. The owner has all the bases covered and goes the extra mile to help with anything you need. I highly recommend this property for your vaction and am already planning our 2015 stay! Thanks again Javier!

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$424

Waterfront Home away from Home

Dunedin apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$109

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Exceptional” We just returned from a 4 week stay at another/similar condo in this same building, same owner. The unit was clean, comfortable, spacious and located in close proximity to everything we needed (i.e. Beach, supermarket, restaurants, shops). John (owner) was more than accomodating with helping us get online (wifi) and being flexible with our schedule. The Gulf view was great and the building was relatively quiet considering it was Spring Break month. Will definitely be returning.

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$240

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

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$286

Viewing 38 of 1,070
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