Oldsmar Rentals

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626 Houses

Secluded Tuscany Home Oasis, 1.5 acre Pool home

Oldsmar house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$285

La Rustic House

Oldsmar house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Heated pool

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Price per night from

$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.

Match: Heated pool

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Price per night from

$161

Water view Bayfront 300 yards from Beach

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Heated pool

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Price per night from

$295

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.

Match: Heated pool

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Price per night from

$104

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$345

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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Price per night from

$92

440 West Condos 508-S Gulf Front Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$481

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$127

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$345

Belle Harbor 1105M Fabulous Luxury 11th Floor View at Belle Harbor

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$585

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$953

440 West Condos 1501-N Condo with a water view

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$847

Belle Harbor 407M Luxury Clearwater Beach Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$318

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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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

Match: Heated pool

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Price per night from

$206

440 West Condos 808-N Beautiful Water View

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$155

Nice mobile home by the canal

St. Petersburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Heated pool

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Price per night from

$96

Exclusive Isla Bonita - Private Pool - Steps from the sand

Indian Rocks Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$923

“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.

Match: Heated pool

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Price per night from

$287

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.

Match: Heated pool

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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!

Match: Heated pool

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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

Match: Heated pool

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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

Match: Heated pool

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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!

Match: Heated pool

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Price per night from

$172

Clearwater Beach Furnished Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$172

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.

Match: Heated pool

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Price per night from

$99

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$481

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

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Heated pool

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Price per night from

$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.

Match: Heated pool

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Price per night from

$172

Cove Cay Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Heated pool

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Price per night from

$54

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

Match: Heated pool

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Price per night from

$246

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.

Match: Heated pool

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Price per night from

$688

Clearwater Beach 3-bedroom Waterfront Luxury Condo

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Heated pool

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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.

Match: Heated pool

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Price per night from

$382

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.

Match: Heated pool

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Price per night from

$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.

Match: Heated pool

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Price per night from

$435

single family home one level, all one family homes community

New Port Richey house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Heated pool

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Price per night from

$66

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