Oldsmar Rentals

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158 Houses

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$195

Great rentals within 20 miles that match your search

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$92

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$205

Cottage Apartment Spring Bayou

Tarpon Springs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

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$149

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

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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$658

Coconut Beach House - Private Pool

Clearwater house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$824

Clearwater Beach Cabana - Private Pool

Clearwater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 26

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Price per night from

$1,712

Sunshine's Hideaway - Beachfront with Private Pool

Indian Rocks Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$1,447

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

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Price per night from

$1,580

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

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

AVALON- POOL VIEW IN A MODERN CONDO - Feel at Home and enjoy your stay

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 32 minutes

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$227

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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$315

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

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$160

Historic Old Northeast Coastal Decorated 1 Bedroom

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$144

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$84

TAMPA BAY WATERFRONT CONDO!

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$158

Woodside Village Condos

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$229

HIstoric home/apartment in the Heart of Tarpon Spr

Tarpon Springs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

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$149

SPACIOUS AFFORDABLE Golden Shores Condo - Indian Shores, FLORIDA

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Lovely vacation on the Gulf Coast” Jill and Peter were very friendly, accommodating hosts. They made sure we had everything we needed and gave us all the information to make us feel like locals to the Indian Shore. The apartment is impeccably clean and spacious. I would recommend this accommodation to anyone looking for a relaxing, sunny vacation on the Gulf Coast!

Responds fast! avg. 3 hours 46 minutes

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Price per night from

$95

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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Price per night from

$286

Cozy carriage apartment in Tarpon Springs

Tarpon Springs apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great stay in Tarpon Springs” What a gem of a place. We had two bedrooms, full kitchen, living area and sun deck. What more could you want! gulf beaches, restaurants etc are all nearby. Super clean with all the necessary amenities including beach chairs, towels etc. The neighborhood is super quiet with lots of old Florida charm. It was three of us traveling including a friend and my husband. We felt right at home! Would highly recommend this place.

Responds fast! avg. 43 minutes

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Price per night from

$149

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

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$482

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

beautiful condo with magnificent views of mandalay

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$153

Avalon at Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Location,Location,Location” Terrific get-a-way. Quiet, comfortable ,very clean, has everything you could want .Very close to other locations such as Tampa ,Dunedin. Beautiful beaches. Fabulous sunsets. .Great restaurants within walking distances. Condo has a beautiful pool. Truly a paradise . A must rental.

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$121

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

Indian Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$198

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.

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Price per night from

$217

Blue house

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$172

Casa Del Mar - Tampa/ Rocky Point

Tampa condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$228

Gulf Front Dreams - Beachfront with a pool!

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$1,184

Reef Club Luxurious 1st Floor Condo

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Spring break” We actually visited last April for spring break ....had a wonderful time with family and friends....would definitely love to stay again sometime....the condo was beautiful

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Price per night from

$286

Waterfront Breeze Condo - Waterfront with a pool!

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$592

Beach Front Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$447

Viewing 38 of 158
rentals in Oldsmar

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