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Clearwater Holiday Vacation with Pools

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663 rentals in Clearwater.
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BEAUTIFUL HARBORVIEW GRANDE, vacation rental in Clearwater

BEAUTIFUL HARBORVIEW GRANDE

Clearwater Beach
3 bedrooms
2 bathrooms
Sleeps 8
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Private Rooftop Terrace with Hut Tub and Stunning Ocean Views !!, vacation rental in Clearwater

Private Rooftop Terrace with Hut Tub and Stunning Ocean Views !!

Clearwater Beach
4 bedrooms
3 bathrooms
Sleeps 13
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Waterfront Beachhouse Steps Away from Nation's #1 Beach, vacation rental in Clearwater

Waterfront Beachhouse Steps Away from Nation's #1 Beach

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 8
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Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico, vacation rental in Clearwater

Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico

Clearwater Beach
2 bedrooms
1 bathroom
Sleeps 5
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Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand., vacation rental in Clearwater

Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand.

Clearwater Beach
3 bedrooms
1 bathroom
Sleeps 10
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Great for Groups! Sleeps 16! Pets Welcome, Pool, vacation rental in Clearwater

Great for Groups! Sleeps 16! Pets Welcome, Pool

Clearwater Beach
4 bedrooms
4 bathrooms
Sleeps 16
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Newly Remodeled Clearwater Beach Condo! 15th Floor 2BR/2Bath, vacation rental in Clearwater

Newly Remodeled Clearwater Beach Condo! 15th Floor 2BR/2Bath

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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A perfect place for a couple, Mango Tango Cottage, vacation rental in Clearwater

A perfect place for a couple, Mango Tango Cottage

Clearwater Beach
1 bedroom
1 bathroom
Sleeps 2
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RENOVATED IN 2017  -  1 BEDROOM, 1 BATH, 750 SQ FEET CONDO, vacation rental in Clearwater

RENOVATED IN 2017 - 1 BEDROOM, 1 BATH, 750 SQ FEET CONDO

1 bedroom
1 bathroom
Sleeps 4
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Waterfront Top Floor, Pet Friendly, W/D, Pool, Marina View, 2 King Beds, Balcony, vacation rental in Clearwater

Waterfront Top Floor, Pet Friendly, W/D, Pool, Marina View, 2 King Beds, Balcony

Clearwater Beach
3 bedrooms
2 bathrooms
Sleeps 8
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SOOOO MUCH OUTDOOR SPACE TO ENJOY, WATER IS GREAT.  VERY SPACIOUS CONDO, vacation rental in Clearwater

SOOOO MUCH OUTDOOR SPACE TO ENJOY, WATER IS GREAT. VERY SPACIOUS CONDO

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Beachcomber Beach House, vacation rental in Clearwater

Beachcomber Beach House

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Cozy Cottage Clearwater, vacation rental in Clearwater

Cozy Cottage Clearwater

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Gulfside and water view on Clearwater beach. 50 steps to the white sand., vacation rental in Clearwater

Gulfside and water view on Clearwater beach. 50 steps to the white sand.

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Dolphin Views |  500 Steps To Sugary White Sands | ActivePur Air Purifier, vacation rental in Clearwater

Dolphin Views | 500 Steps To Sugary White Sands | ActivePur Air Purifier

Clearwater Beach
3 bedrooms
2 bathrooms
Sleeps 6
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MAGNIFICENT BEACHFRONT 2 BED 2 BATH CONDO-POOL, ON THE BEACH, vacation rental in Clearwater

MAGNIFICENT BEACHFRONT 2 BED 2 BATH CONDO-POOL, ON THE BEACH

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Key West Style Home. Covered Porch w/GULF VIEW. all Beach Gear. 30 Secs to Sand!, vacation rental in Clearwater

Key West Style Home. Covered Porch w/GULF VIEW. all Beach Gear. 30 Secs to Sand!

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 7
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Condo.Ocean front.Famous Sandpearl Resort & Spa, vacation rental in Clearwater

Condo.Ocean front.Famous Sandpearl Resort & Spa

Clearwater Beach
1 bedroom
1 bathroom
Sleeps 4
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Clearwater Beach Luxury Condo, vacation rental in Clearwater

Clearwater Beach Luxury Condo

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 8
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Right on the BEACH!    Exclusive Lighthouse Towers,  Sand Key,  Clearwater Beach, vacation rental in Clearwater

Right on the BEACH! Exclusive Lighthouse Towers, Sand Key, Clearwater Beach

1 bedroom
2 bathrooms
Sleeps 4
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BEACHFRONT Weekly Rental, vacation rental in Clearwater

BEACHFRONT Weekly Rental

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 5
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Beachfront Corner Penthouse, Water Views Every Window., vacation rental in Clearwater

Beachfront Corner Penthouse, Water Views Every Window.

2 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Townhome on Brightwater Drive, vacation rental in Clearwater

Waterfront Townhome on Brightwater Drive

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 6
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BEACH VIEW! Charming Cozy Cottage. Best Location 1BR/1BA Deck,Patio.,Beach Gear!, vacation rental in Clearwater

BEACH VIEW! Charming Cozy Cottage. Best Location 1BR/1BA Deck,Patio.,Beach Gear!

Clearwater Beach
1 bedroom
1 bathroom
Sleeps 4
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Luxury Beachfront Penthouse, 53' Beachfront Balcony, 3 bdrm, 2400 sf , 4th floor, vacation rental in Clearwater

Luxury Beachfront Penthouse, 53' Beachfront Balcony, 3 bdrm, 2400 sf , 4th floor

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 8
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Beach-Front Paradise w/ Water Views at Every Window, vacation rental in Clearwater

Beach-Front Paradise w/ Water Views at Every Window

2 bedrooms
2 bathrooms
Sleeps 5
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1BR/1BA NEW Coastal Boutique Cottage. HGTV Worthy! Sleeps 4. Steps to Beach!, vacation rental in Clearwater

1BR/1BA NEW Coastal Boutique Cottage. HGTV Worthy! Sleeps 4. Steps to Beach!

Clearwater Beach
1 bedroom
1 bathroom
Sleeps 4
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NEW - Waterfront Townhome w/Elevator/Boat Slip/ Pool/ - BEST LOCATION !, vacation rental in Clearwater

NEW - Waterfront Townhome w/Elevator/Boat Slip/ Pool/ - BEST LOCATION !

Clearwater Beach
4 bedrooms
4 bathrooms
Sleeps 10
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Famous Sandpearl Resort King Penthouse-Direct Ocean Views From Every Room, vacation rental in Clearwater

Famous Sandpearl Resort King Penthouse-Direct Ocean Views From Every Room

Clearwater Beach
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Avalon at Clearwater, vacation rental in Clearwater

Avalon at Clearwater

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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LUXURY 5*CONDO WATER FRONT,3 BEDS,2 BATH,POOL,HOT TUB,,WI-FI,POOL/BEACHES OPEN, vacation rental in Clearwater

LUXURY 5*CONDO WATER FRONT,3 BEDS,2 BATH,POOL,HOT TUB,,WI-FI,POOL/BEACHES OPEN

Clearwater Beach
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury condo overlooking gorgeous pool, vacation rental in Clearwater

Luxury condo overlooking gorgeous pool

2 bedrooms
2 bathrooms
Sleeps 6
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Luxury Waterfront Condo on Clearwater Beach. 3 Bedrooms, 2 Full Baths, Sleeps 8, vacation rental in Clearwater

Luxury Waterfront Condo on Clearwater Beach. 3 Bedrooms, 2 Full Baths, Sleeps 8

Clearwater Beach
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Waterfront, 3 BR/3 BA, Water Views, Walk to All, vacation rental in Clearwater

Luxury Waterfront, 3 BR/3 BA, Water Views, Walk to All

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 8
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BEST SOCIAL DISTANCE Caladesi House, CLEARWATER PRIVATE BEACH AREA, PRIVATE POOL, vacation rental in Clearwater

BEST SOCIAL DISTANCE Caladesi House, CLEARWATER PRIVATE BEACH AREA, PRIVATE POOL

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 5
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Stunning NEW 2BR/2BA Executive Beach Home Steps to Sand. Loaded w/Everything!, vacation rental in Clearwater

Stunning NEW 2BR/2BA Executive Beach Home Steps to Sand. Loaded w/Everything!

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 4
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Sun West Palms - Suite 203 - 3 Bed Room - 3 Bathroom., vacation rental in Clearwater

Sun West Palms - Suite 203 - 3 Bed Room - 3 Bathroom.

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 8
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The Beachy Bungalow is Rolling Back it's Prices, BOOK NOW!!!, vacation rental in Clearwater

The Beachy Bungalow is Rolling Back it's Prices, BOOK NOW!!!

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 4
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Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach, vacation rental in Clearwater

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A perfect view from your balcony...just the right amount of sand, sea and sky, vacation rental in Clearwater

A perfect view from your balcony...just the right amount of sand, sea and sky

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Cottage Clearwater Bch, Heated Pool, 2/2 Tangerine Dream, vacation rental in Clearwater

Cottage Clearwater Bch, Heated Pool, 2/2 Tangerine Dream

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 5
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Amazing Beachfront Getaway!, vacation rental in Clearwater

Amazing Beachfront Getaway!

Clearwater Beach
2 bedrooms
2 bathrooms
Sleeps 6
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Townhome on the water with Private Entrance, 3 King Beds - NOT a high rise Condo, vacation rental in Clearwater

Townhome on the water with Private Entrance, 3 King Beds - NOT a high rise Condo

Clearwater Beach
3 bedrooms
4 bathrooms
Sleeps 10
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Water Views From Every Window--Right on the Beach!, vacation rental in Clearwater

Water Views From Every Window--Right on the Beach!

2 bedrooms
2 bathrooms
Sleeps 4
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Easy one minute walk to #1 beach!, vacation rental in Clearwater

Easy one minute walk to #1 beach!

Clearwater Beach
3 bedrooms
2 bathrooms
Sleeps 6
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2 Bedroom cottage, Sleeps 6; 5 minutes to Beach, vacation rental in Clearwater

2 Bedroom cottage, Sleeps 6; 5 minutes to Beach

2 bedrooms
2 bathrooms
Sleeps 6
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Orange Blossom-Key Lime Cottage-2 Pools-Clwtr Beach, vacation rental in Clearwater

Orange Blossom-Key Lime Cottage-2 Pools-Clwtr Beach

Clearwater Beach
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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3 Bed / 3 Bath Luxury Waterfront Condo. Sleeps Up To 8., vacation rental in Clearwater

3 Bed / 3 Bath Luxury Waterfront Condo. Sleeps Up To 8.

Clearwater Beach
3 bedrooms
3 bathrooms
Sleeps 8
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Royal Paradise - Avalon at Clearwater | Minutes to Clearwater Beach, vacation rental in Clearwater

Royal Paradise - Avalon at Clearwater | Minutes to Clearwater Beach

2 bedrooms
2 bathrooms
Sleeps 6
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Cozy and Friendly - Only 75 Steps to Clearwater Beach, vacation rental in Clearwater

Cozy and Friendly - Only 75 Steps to Clearwater Beach

Clearwater Beach
2 bedrooms
1 bathroom
Sleeps 5
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About Clearwater
If you've been looking for the perfect Gulf Coast destination with well-maintained beaches and ample family-friendly activities, set your sights on Clearwater, Florida. With beautiful beaches, Clearwater vacation homes right on the water, and numerous festivals, this is a beach town you'll want to revisit year after year.
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About Clearwater
If you've been looking for the perfect Gulf Coast destination with well-maintained beaches and ample family-friendly activities, set your sights on Clearwater, Florida. With beautiful beaches, Clearwater vacation homes right on the water, and numerous festivals, this is a beach town you'll want to revisit year after year.
Clearwater Climate
Like much of Florida's Gulf Coast, Clearwater is known for its hot, humid summers and pleasantly mild winters. The area's busiest seasons for tourism include spring and summer, when temperatures reach the upper 80s and several inches of rain fall each month. Clearwater vacation homes continue to be popular through the fall and winter, when temperatures remain in the 70s and much less rain falls.
How to Get Around Clearwater
Getting to Clearwater is easy, since several airports serve the area. The most convenient option is the St. Pete - Clearwater International Airport, which is just a 25-minute drive from most Clearwater vacation homes. Tampa International Airport, a larger facility with more daily flights, is just a 30-minute drive from Clearwater. Once you're in town, it's easy to get around without a car. To get to most major attractions in downtown Clearwater, rely on the Jolley Trolley. On the beach itself, most sights are within easy walking distance. You can also hop on the Suncoast Beach Trolley to reach several neighboring communities.
Top Things to Do in Clearwater
For most visitors, Clearwater Beach is a necessary first stop. This popular beach has everything you need, from cabanas to umbrellas, along with plenty of space to sunbathe or swim. Nearby, Sand Key Park offers a more low-key destination for families, with playgrounds, walkways, and picnic areas. You'll see plenty of fish in the Gulf, but to get up close and personal with some of the most fascinating species, head to the Clearwater Marine Aquarium. Here you'll see everything from dolphins to stingrays to turtles. If you're visiting Clearwater during Major League Baseball's spring training season, don't miss your chance to see your favorite teams play at Bright House Networks Field. In the evening, get your friends together or take your date to Ruth Eckerd Hall, a much-loved concert venue in the heart of Clearwater.
Can't-Miss Clearwater Events
In the spring, start the season off with the Firestone Grand Prix, which takes off on the seaside course in neighboring St. Petersburg. You'll experience a weekend of races and an entire week of fun and excitement. Later in the spring, catch the Tampa Bay Blues Festival, a major event for blues fans for over two decades. Along with the genre's best live performers, you'll find great food and plenty of sunshine. In the fall, make your way to the Clearwater Super Boat National Championship and Seafood Festival, which boasts competitions that will get your heart racing and some of Clearwater's best seafood. October brings the Clearwater Jazz Holiday to town, which includes four days of jazz greats and warm weather.