Holiday Rentals with Pools

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363 Houses in Holiday with pools

Match: Swimming pool

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Price per night from

$201

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.

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Price per night from

$229

Great rentals within 20 miles that match your search

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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Price per night from

$172

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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Price per night from

$161

Water view Bayfront 300 yards from Beach

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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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.

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Price per night from

$103

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$567

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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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: Swimming pool

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Price per night from

$480

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$1,227

440 West Condos 1408-N Gulf Front Condo with amazing views

Clearwater apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Responds fast! avg. 50 minutes

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Price per night from

$179

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$1,417

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

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Price per night from

$126

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

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$584

Belle Harbor 603M Posh Pineapple

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$344

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$951

440 West Condos 1501-N Condo with a water view

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$845

Belle Harbor 407M Luxury Clearwater Beach Condo

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$318

Bay Harbor 301 Beautiful Waterfront Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$1,492

Private Island Oasis on Gulf with Stunning Views

Hudson condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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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

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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

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Price per night from

$155

Lovely Tropical Sunlit bedroom

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$228

Mediterranean Lakefront Mansion

Tampa house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 20

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Price per night from

$1,140

Coconut Beach House - Private Pool

Clearwater house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$824

Clearwater Beach Cabana - Private Pool

Clearwater house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 26

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Price per night from

$1,712

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$401

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: Swimming pool

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Price per night from

$54

Brightwater Point 105 Grand Water Views

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect in every way!” Perfect location; beautiful condo; everything we needed. If I could have a negative comment it would be that the couch was a little uncomfortable. I can't say enough about how perfect; we have made arrangements to return!

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$1,045

Bay Breeze House Waterfront home with pool

Clearwater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$541

Island Key Condos 303 Large Balcony overlooking Bay

Clearwater apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Amazing” We were first time renters and we're very anxious. We couldn't have been more impressed. There was so much space and the condo was spotless. The area was quiet and the apartment block was spotless. The pool was heated and spa was hot. The staff in the office were so nice and helpful made us feel really valued. Will definitely be returning and would highly recommend the rental company.

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$280

Villas of Clearwater Beach 2B Renovated condo that is just Steps to the beach an

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$210

Villas of Clearwater Beach 6B Almost Beachfront

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

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Price per night from

$272

“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: Swimming pool

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Price per night from

$287

“Harbor View Grande Suite # 707 Excellent 5 Star *****” A Big Thank you to the owners and Staff of 707. The accommodations where beyond our expectations. The décor was professionally done and the Suite was spotless upon arrival. The champagne was a special treat and all the beach chairs, umbrellas, coolers for our use was that extra touch. Harborview is centrally located to all shops and restaurants. The balcony views from sunrise to sunset was truly magnificent. Highly recommend to all friends and relatives. Will definitely return. Thanks again. Anthony David

Match: Swimming pool

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Price per night from

$269

Comfy Cozy Cul de Sac Home in Beacon Woods East

Hudson house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$134

Clearwater Beach Furnished Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming 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: Swimming pool

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Price per night from

$480

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