Oldsmar Rentals

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800 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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$285

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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$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

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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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

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$953

Belle Harbor 407M Luxury Clearwater Beach Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$318

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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$206

Quiet Waterfront Home, Gulf-access

Tarpon Springs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$241

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

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

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$1,583

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

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

Waterfront Home away from Home

Dunedin apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 35 minutes

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$109

"Something Fishy" Beach Front Condo & Sunset Views

Indian Rocks Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$167

Sea Breeze 108 (Madeira Beach) Beautiful, Tranquil Beach Front Condo

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 33 minutes

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$247

Clearwater Beach Furnished Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$172

* Busch Gardens " Welcoming & Comfortable"

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Sunshine State Vacation Well Done!” We had an amazing time in this lovely Florida rental. I would highly recommend this place for families with kids. The house is clean and conveniently located near many fun things to do. Disney is only hour and fifteen minutes away which made easy for one day visit to Magic Kingdom! Host was friendly and resourceful. He was quick to respond to all of our questions and he offered advice on many great things to do in the area!

Responds fast! avg. 2 hours 59 minutes

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$179

Indian Shores Condo

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very good, lovely view, handy for beach” A nice location close to beach and with beautiful view over inland waterway. Well kept apartment with on-site facilities.

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$99

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$481

Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$483

SUNNY ALL DAY modern condo near Gulf of Mexico beaches

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“CLEARWATER'S BEST KEPT SECRET” The pictures sold me on this condo. It is exactly as it shows. Very clean, smells good. Great locations, all stores close on the same road as condo. Close to the beach. Owner kept in close contact throughout our pre-booking and stay. I will stay here again! Very, very nice.

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$172

Wonderful Belleair Beach Condo

Belleair Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$144

Dolphin House Short Walk To The Beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 50 minutes

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$359

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$293

EIKO BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK

Treasure Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

“Water, water everywhere” So very, very close to the beach. Very helpful agent. Had 11 people with plenty of room .awesome time.

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$688

HOME AWAY FROM HOME ..

Indian Rocks Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful stay in Indian Rocks Beach” My wife and I celebrated our 31st anniversary and stayed in Sharif and Sabine's condo 202 Reef Club 1000 Gulf BLVD. They bent over backwards to make sure our stay was incredible. They asked us to do a quick run through of the unit and if there was anything dirty or needed repair to call immediately. We called on a toilet issue and over the phone we repaired it within minutes. They also had beach chairs umbrella and toys to play with so we did not need to bring anything with us. We are looking forward to our next stay. I have business in Tampa and usually stay at a hotel. if this unit is open, it was less expensive and had tons more room.

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$1,148

Beach Dreams - Beach Cottage 2103

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great unit, perfect location” Been coming to Beach Cottage for over ten years and love the decor and location of Beach Cottage 2103. Indian Shores Vacation is the only place we think of for summer beach vacation.

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$435

**PERFECT FOR A FAMILY VACATION** 3Br Directly On The Beach

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$199

Tropical Island Retreat-Private Waterfront

Tarpon Springs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$345

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