Oldsmar Rentals

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795 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

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$343

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$275

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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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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$2,172

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

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$1,581

Westwinds Paradise - Private Pool - Steps from the sand!

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$921

Exclusive Isla Bonita - Private Pool - Steps from the sand

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$921

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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$476

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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$458

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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$423

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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$166

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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$172

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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$480

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

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$482

Waterfront Penthouse Condo on Intercoastal Across from Beach

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great views” Great place in a good location and awesome views of the intercoastal. Enjoyed sitting on the patio and watching the boats go by. Would definitely stay there again if i am in the area.

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$224

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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$292

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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$1,145

“Great cozy home away from home.” We stayed in the Orleans bungalo apartment on July 15-18. It felt like we were at home. The apartment had lots of character and charm. Loved sitting outside on the terrace watching the free entertainment across the street , was it called the ship wrecked bar? I especially loved beiing able to go to the back alley and washing clothes. (I hope it belonged to the cottages property, if not then oops!) We utilized the kitchen and the gas grill out back on the patio.Everything was great and this cottage had plenty of space for two families. We met my cousins from Texas in Flordia for a vaca. We drove from Oklahoma. The flat screens worked great. I have no complaints about this place. I just want to say to all you all snotty people leaving negative comments.... Quit complaining or find somewhere else to stay. What exactly do you think you are getting when you hear the word "cottages" it's not going to have a bell hop and a maid that cleans up your messes daily. Maybe some of you never lived in 100 year old homes and only used to a lavish lifestyle. Obviously you spent your time in doors. not us we were at the beach the majority of the day until almost 9pm every night. I enjoyed my stay there. It was a good 3 day stay for us despite the rainy weather. Yet we still had fun.

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$297

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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$434

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

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$198

Tropical Island Retreat-Private Waterfront

Tarpon Springs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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$344

3 bedroom / 2bath Large Condo on the Beach

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“SunSet Paradise condos” It was a nice condo - outside of the fact that the tv in the main room was non functional and when we texted the owner, we never got a reply Other than that - very good vacation!!!!

Responds fast! avg. 2 hours 7 minutes

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$287

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$205

Beach Front Condo In Indian Rocks Beach

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 41 minutes

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$210

Waterfront Island Pool Home with Hot Tub and Canoe!!

Tarpon Springs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$315

Surfside Villas - steps from the beach

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Amazing” Absolutely beautiful! Condo is great and the area is phenomenal, Tom is the perfect host! Definitely coming back

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$258

Beachside Efficiency in Treasure Island (Blue)

Treasure Island apartment

  • 1 bathroom
  • sleeps 2

“Perfect location” The location of this stay is just amazing for the price. It's not directly on the beach but it practically feels like it is because there it is less than one minute to get to the beach without crossing any major road. The place is small, but it worked perfectly for just 2 people. Doesn't have a stove or oven so you have to resort to fruits or microwave food but it's not a big deal as there are tons of restaurants nearby. Only issue we really had was that you could hear either the neighbors next door or the above us running around and banging but it wasn't for too long and wasn't too bad. We had ignored it pretty quickly if that helps. For longer stays, be sure to get toilet paper and possibly soap. Also there is no way to wash clothes so pack a lot if this is your only stay. I don't believe there was an outdoor shower to wash off the sand before going in, but honestly we could have just missed where it was. Overall, really nice place, can't beat the price for the location.

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$86

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