Holiday Rentals

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230 Houses

Match: Heated pool

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Price per night from

$200

Geodesic Dome

Holiday apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Will and already have recomend to others.” Lots of fun places to see and eat at nearby. Sharon and Ralph made sure we had everything we needed.

Match: Heated pool

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Price per night from

$229

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

$160

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Heated pool

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Price per night from

$172

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Heated pool

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Price per night from

$84

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

$294

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

$103

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

$478

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

$582

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

$126

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

$343

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

$947

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

$842

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

$316

Private Island Oasis on Gulf with Stunning Views

Hudson condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$172

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

$154

Coconut Beach House - Private Pool

Clearwater house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$821

Clearwater Beach Cabana - Private Pool

Clearwater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 26

Match: Heated pool

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Price per night from

$1,706

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.

Match: Heated pool

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Price per night from

$655

Luxury Florida Villa - Waterfront with Private Pool

Crystal Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Heated pool

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Price per night from

$984

The Cobbles

Hudson villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 24 minutes

Match: Heated pool

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Price per night from

$172

Surfside Condos 204 Beachfront Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Surfsude Condo 204” The view was great....the condo was roomy enough for our family. Everything was good except needed more instruction on using TV in living room. Also needed more electrical outlets. We would stay here again. Had a great time.

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$54

Villas of Clearwater Beach 6B Almost Beachfront

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$271

“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

$286

Clearwater Beach Furnished Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$172

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

$478

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

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

$364

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

$65

Waterfront Island Pool Home with Hot Tub and Canoe!!

Tarpon Springs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Heated pool

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Price per night from

$314

Luxury 3BR GulfFront "Grateful to be at the Gulf"

Hudson apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 59 minutes

Match: Heated pool

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Price per night from

$99

Affordable Luxury Directly On The Gulf Of Mexico.

Clearwater apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

Match: Heated pool

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Price per night from

$172

Beautiful 2 bedroom condo,mins. drive to beach, pool

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$206

Belle Harbor 404M Waterfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

Match: Heated pool

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Price per night from

$206

Tarpon Woods Condo with Lake View

Palm Harbor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Heated pool

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Price per night from

$57

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