Oldsmar Rentals

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424 Houses

Flamingo Bungalow Beautiful Tampa Retreat

Oldsmar apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$195

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$286

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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Price per night from

$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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Price per night from

$345

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$92

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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Price per night from

$206

Quiet Waterfront Home, Gulf-access

Tarpon Springs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$241

Mediterranean Lakefront Mansion

Tampa house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

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Price per night from

$1,142

Beachfront - Indian Shores - Inquire summer special BOGO

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$276

8 houses from beach and gulf in Clearwater beach

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$263

Sandy Shores Beach House - Beachfront Home

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$627

3 Palms Retreat - Beachfront

Indian Rocks Beach house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

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Price per night from

$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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Price per night from

$923

Art's Beach Retreat

Belleair Beach villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$287

Key West Style Beach House

Indian Rocks Beach townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$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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Price per night from

$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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Price per night from

$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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Price per night from

$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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Price per night from

$286

"Something Fishy" Beach Front Condo & Sunset Views

Indian Rocks Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$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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Price per night from

$247

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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Price per night from

$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

Beautiful Beachfront Condo on the FL Gulf Coast

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful family beach vacation condo” The condominium is a great place to stay. All the amenities you need to enjoy a relaxing family vacation. There is an picturesque view of the beach on the balcony and a large pool to enjoy. The location of the condo is convenient to shopping and restaurants. Carol (the owner) is always very helpful and accessible if you have any questions about your stay. We have found a new place to stay on our summer vacation and can't wait to visit again next year!

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Price per night from

$241

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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Price per night from

$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

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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$173

beautiful condo with magnificent views of mandalay

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$153

Wonderful Belleair Beach Condo

Belleair Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$144

Oceanfront 1400 sq ft Condo at Beach Cottage One! Private Beach, Big Pool

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“We had a great vacation at this condo.” My family has been visiting indian rocks beach for nearly two decades, and we continue coming back to this resort and specifically, Martin's condo. It is always kept updated and we had a nice relaxing stay. It has WiFi for the kids and has a picture perfect view of the beach, ocean, sunsets and pool deck. You won't be disappointed.

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$246

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$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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Price per night from

$688

Clearwater Beach 3-bedroom Waterfront Luxury Condo

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$366

Sunsets, Cocktails and Memories!

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Spacious and beautiful” My girlfriends and I just finished our stay for the third year in a row. This is an outstanding condo. With four or five of us, there is plenty of room. The private spiral staircase to the beach is great! No waiting for the elevator with everyone else. We love sitting on the porch early in the morning and again at sunset. Spectacular views! Also you can visit the Suncoast Seabird Sanctuary which is about 1/2 block to the south. Would highly recommend this condo. We hope to be back again next year.

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Price per night from

$383

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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Price per night from

$1,148

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