Oldsmar Rentals

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1,128 Houses

Dolphin Bay Retreat

Oldsmar house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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$287

Florida Blue House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$183

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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$286

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$327

La Rustic House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$389

Great rentals within 20 miles that match your search

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

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$161

Water view Bayfront 300 yards from Beach

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$295

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

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$153

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

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$568

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

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$201

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$206

Cottage Apartment Spring Bayou

Tarpon Springs apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 43 minutes

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$150

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$276

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

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$402

Key West Style Beach House

Indian Rocks Beach townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$153

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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$150

“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

Responds fast! avg. 2 hours 35 minutes

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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

"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

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

$150

La Buena Vida II at Captains Cove, Indian Shores, Florida - Come, relax, enjoy!

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very clean and comfortable. Walking distance to everywhere and a great view” Great place to stay. I felt very comfortable and relaxed, this place has a very beachy relaxing vibe in a prime location. You literally do not have to drive anywhere while you're here, everything I wanted was in walking distance!

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Price per night from

$173

Clearwater Beach Furnished Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$173

* 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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Price per night from

$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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Price per night from

$481

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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Price per night from

$224

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