Clearwater, FL Vacation Rentals

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Filtering by: Swimming pool

1,632 beach rentals in Clearwater with pools

Dog-Friendly 2BR, 2BA Clearwater House w/ Pool, 5 Miles from the Beach

Clearwater house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$125

3BR w/ Roof Deck on Waterway

Clearwater house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$208

Beautiful relaxing getaway close to the beach

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 3

“Beautiful condo, close proximity to beach, relaxing and lovely stay!!” We had such a lovely time at the condo. The owners are incredibly wonderful to communicate with and so gracious and attentive to needs. The place was spotless and beautifully decorated. It truly felt at home and was very convenient access to the beach area. Only less than 10 minutes drive. We had a wonderful stay, everything was in wonderful condition and we were extremely comfortable! The pool was lovely and a perfect temperature. And the condo was decorated in a beautiful way and was very lovely to stay in. Pamela and Kevin have truly made it a gorgeous and homey feel and we were so lovely to interact with and we had everything we could possibly need!! Thank you for a wonderful stay :)

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Price per night from

$81

Remodeled 2brms Condo. Fantastic location! 15 min from Clearwater beach

Clearwater apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 54 minutes

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Price per night from

$92

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

4 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$399

Surfside Condos 202 Beachfront Condo

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Wonderful !” This condo was perfect for what we needed. As only a couple, the master bedroom was wonderful with it’s king size bed and a sliding door to the deck . It has a great oceanfront view and we had awesome sunsets every night from our balcony. Our favorite beach walks were at sunset. We really enjoyed all the recliners on the love seat and couch. They have a large basket of beach towels we used every day. And Vacation Rental took good care of us , too. I would stay here again for sure!

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Price per night from

$188

Romance On The Beach! Great View of the Beach!

Clearwater apartment

/ 1 bathroom / sleeps 2

“Awesome Bungalow” This little bungalow is within walking distance of the beach. The owners did a beautiful job with the remodel. Nice little deck where you can drink coffee in the morning and enjoy a glass of wine while watching the sunset. This is a lovely unit and very quiet.

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Price per night from

$178

LUXURY for LESS ! Modern Comfort, Near Beaches, Shops, Restaurants

Clearwater condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 28 minutes

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Price per night from

$75

Clearwater Beach Waterfront Townhouse on the ICW

Clearwater townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 54 minutes

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Price per night from

$288

404 Dockside

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 11 minutes

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Price per night from

$145

Lavish 3BR Condo w/ Outdoor Patio, Hot Tub, Pool & Intracoastal Waterway View

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$203

beautiful condo with magnificent views of mandalay

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$91

Bay Harbor Condo in Clearwater Beach

Clearwater condo

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$231

Avalon at Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

“Location,Location,Location” Terrific get-a-way. Quiet, comfortable ,very clean, has everything you could want .Very close to other locations such as Tampa ,Dunedin. Beautiful beaches. Fabulous sunsets. .Great restaurants within walking distances. Condo has a beautiful pool. Truly a paradise . A must rental.

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Price per night from

$99

LUXURY 5*SUITE,3 BEDS,2 BATH,POOL,HOT TUB,WATER VIEWS.2019 /2020 RATES REDUCED

Clearwater condo

3 bedrooms / 2 bathrooms / sleeps 10

“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

Responds fast! avg. 3 hours 25 minutes

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Price per night from

$247

Clearwater Beach Cambria House

Clearwater house

3 bedrooms / 2 bathrooms / sleeps 6

“Perfect!” This place is perfect. Amazing location short walk to everything but far enough away from the busy area to be very peaceful.the cleanest rental place I have ever stayed, and stocked with everything you might need. Highly recommend a stay here for an amazing get away.

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Price per night from

$384

GulfSideSuite at 30 seconds Walk to the Beach. WOW

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 2

“Lovely apartment, location, beach access, owner,and manager” Really 30 seconds to beautiful white sand beach! The tides are gradual and can leave multitudes of shells or pristine sand. We walked several miles north and south on the beach whenever we wanted. This brought us to restaurants, Pier 60 and shopping. The intercoastal waterway is an easy walk across the road. The efficiency apartment had lovely private area outside to relax, comfortable bed and kitchenette, stocked with everything we needed, perfect for our 2 week stay,The owner and manager were easily contacted and super friendly. Community swimming pool and tennis courts are a quick walk. The pool was closed during our stay, bring your own rackets for tennis. We will try to return when we can.

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Price per night from

$202

IT'S WARM HERE! The Blue Heaven, AMAZING Beach Condo

Clearwater condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 18 minutes

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Price per night from

$259

YOUR HOME AWAY FROM HOME from CLEARWATER BEACH!!!

Clearwater condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$99

Special $189/Night!

Clearwater house

5 bedrooms / 3 bathrooms / sleeps 22

Responds fast! avg. 2 hours 42 minutes

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Price per night from

$218

Bay Harbor 401 4th Floor Condo with Panoramic Water View

Clearwater apartment

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$147

304 Island Key

Clearwater condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 11 minutes

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Price per night from

$149

Waterfront Studio on Clearwater Beach

Clearwater studio

Studio / 1 bathroom / sleeps 2

“Room C4!” We really enjoyed our trip to Clearwater! This condo is in a fantastic spot, within walking distance to everything. It has a cute little courtyard, pool, and a fantastic dock to fish off of and watch the dolphins swimming. It was just my husband and I staying so the room was ok. The pictures make it look bigger than it is. The room is very cute and charming and has a great view but it is very small and the bed is not comfortable at all. Good thing we weren't there just for the room! We would actually stay here again but mainly because the location location location! Also the owner was very nice and responded to all of our questions via email very quickly and helped us make arrangements for a late check in. We are hopefully planning on returning with our kids next time!

Responds fast! avg. 3 hours 16 minutes

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Price per night from

$134

Clearwater Beach Cottage w/ Pool Near Sugary Sand!

Clearwater house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$201

Luxury Clearwater Beach Villa w/ Waterfront Views!

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$181

Dock of the Bay - Beautiful Upscale Waterfront 2 KING BR/2BA Condo

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 35 minutes

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Price per night from

$270

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

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Loved this place” Absolutely gorgeous place. So clean and accomadated my family well. Had everything you needed!! Will be booking again!!

Responds fast! avg. 13 minutes

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Price per night from

$127

Affordable Luxury Directly On The Gulf Of Mexico.

Clearwater apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 43 minutes

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Price per night from

$87

Elegant Beach Front Penthouse on Desirable Belleair Beach, FL 2B/2B

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$168

Clearwater Beach 3-bedroom Waterfront Luxury Condo

Clearwater condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$150

PRIVATE POOL HOME IN THE HEART OF CLEARWATER!

Clearwater house

2 bedrooms / 2 bathrooms / sleeps 5

“Great!!!” My wife and I stayed here for our honeymoon and the stay was fantastic! The house was beautiful and John was very helpful!

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Price per night from

$213

Crescent Beach Club

Clearwater condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$304

(2024) Cozy Villa in Sunny Clearwater, Florida

Clearwater villa

2 bedrooms / 2 bathrooms / sleeps 4

“very comfortable” the villa was extremely clean and comfortable! A great place to rent with no inconvenience. Definitely a recommendation! Thank you!

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Price per night from

$111

2 BR/2 BA Waterfront Condo In The Heart of Clearwater Beach!!

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$139

Clearwater Beach Budget Beauty

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 6

“Great Waterview Getaway” We stayed here for a week at the end of May. The unit had a good supply of everything needed to make our stay easy and fun. The kitchen was easy to work in and had more dishes and pans than most places we have stayed in. Nice patio area, pool and view of the intercostal. Good restaurants close by. The staff was friendly and very helpful. Great sunrises too. Parking is ample for all guests.

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$158

New listing: Pool View In Avalon at Clearwater, Fully renovated !

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 27 minutes

Match: Swimming pool

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Price per night from

$98

404 Bay Harbor

Clearwater apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 11 minutes

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Price per night from

$160

Clearwater Beach Condo 3BR fits 6-10

Clearwater condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 21 minutes

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Price per night from

$229

Viewing 38 of 1,632
rentals in Clearwater

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