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Swimming pool
Wireless Internet
Air conditioning
Private pool

Heated pool
Private indoor pool
Washing machine
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Fax machine
Pool or snooker table
Table tennis
Games room
Shared outdoor pool (heated)
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Video player
Climbing frame
Boat available
Fridge
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Freezer
Staffed property
Microwave
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible
Secure parking

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Beach or lakeside relaxation
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
Water sports
Horse riding
Fishing
Waterfront
Golf within 30mins drive
Lakefront

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363 Houses in Holiday with pools

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Location, Location, Water Veiw, Pool Home on Dead End Street! Beauitful Sunsets

Holiday house

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

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.

Match: Swimming pool

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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

All filters match

Price per night from

$172

Luxury waterfront Condo Rooftop Terrace

Clearwater house

3 bedrooms
3 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$567

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

1 bedroom
1 bathroom

sleeps 4

Match: Swimming pool

All filters match

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

All filters match

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

All filters match

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

Match: Swimming pool

All filters match

Price per night from

$179

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$126

Harborview Grande 602 Beautiful Condo Hardwood floors

Clearwater apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$1,417

Belle Harbor 603M Posh Pineapple

Clearwater apartment

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$344

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: Swimming pool

All filters match

Price per night from

$584

440 West Condos 1402-N Gorgeous Waterview Condo

Clearwater apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

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

All filters match

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

Match: Swimming pool

All filters match

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

All filters match

Price per night from

$1,492

Private Island Oasis on Gulf with Stunning Views

Hudson condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$172

Royal Marina | Avalon at Clearwater | Minutes to Clearwater Beach

Clearwater condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

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: Swimming pool

All filters match

Price per night from

$155

Lovely Tropical Sunlit bedroom

Clearwater house

1 bedroom
1 bathroom

sleeps 3

Match: Swimming pool

All filters match

Price per night from

$228

Mediterranean Lakefront Mansion

Tampa house

6 bedrooms
6 bathrooms

sleeps 20

Match: Swimming pool

All filters match

Price per night from

$1,140

Clearwater Beach Cabana - Private Pool

Clearwater house

7 bedrooms
4 bathrooms

sleeps 26

Match: Swimming pool

All filters match

Price per night from

$1,712

Luxury Florida Villa - Waterfront with Private Pool

Crystal Beach house

5 bedrooms
4 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$987

Clearwater Beach Waterfront - With Private Rooftop Terrace

Clearwater townhouse

3 bedrooms
3 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$476

Belle Harbor 404M Waterfront Condo

Clearwater apartment

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$206

Tarpon Woods Condo with Lake View

Palm Harbor condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$58

POOL VIEW modern condo near Gulf of Mexico Beaches. Retreat for two

Clearwater condo

1 bedroom
1 bathroom

sleeps 2

Match: Swimming pool

All filters match

Price per night from

$172

Relaxation at the Tropical Pool House

Tampa house

4 bedrooms
2 bathrooms

sleeps 12

Match: Swimming pool

All filters match

Price per night from

$446

BEACH-FRONT! July- Aug 2024 Availability!

Clearwater condo

1 bedroom
2 bathrooms

sleeps 4

Match: Swimming pool

All filters match

Price per night from

$84

Harborview Grande 507 Beachy and family-friendly

Clearwater apartment

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$1,052

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: Swimming pool

All filters match

Price per night from

$103

Woodside Village Condos

Clearwater condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Swimming pool

All filters match

Price per night from

$229

The Cobbles

Hudson villa

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 24 minutes

Match: Swimming pool

All filters match

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: Swimming pool

All filters match

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

All filters match

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

All filters match

Price per night from

$541

Villas of Clearwater Beach 8B Spacious Beach Condo

Clearwater apartment

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$265

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

All filters match

Price per night from

$280

Viewing 38 of 363
rentals in Holiday

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Holiday Rentals with Pools

Per night

363 Houses in Holiday with pools

Viewing 38 of 363rentals in Holiday

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Viewing 38 of 363
rentals in Holiday