Holiday Rentals with Pools

Updating...

age 0-16
363 Results

Relevance

Price: low to high

Price: high to low

Reviews

363 Houses in Holiday with pools

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

All filters match

Price per night from

$229

Great rentals within 20 miles that match your search

Dunedin Relax in our Updated condo

Dunedin house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

All filters match

Price per night from

$89

CLEARWATER GETAWAY HOME 3BED 2BATH WITH POOL

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

All filters match

Price per night from

$482

Belle Harbor 509M Stunning Luxury Condo with Panoramic Water View.

Clearwater condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$337

440 West Condos 1708-N Stunning 17th Floor Gulf View Condo

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$335

Harborview Grande 306 Waterfront 3 Bedroom 2 Bath Condo

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$446

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$479

"Aqua Villa" 3 bed 2 bath w/ Heated Pool by TPA Airport

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$957

Bay Harbor 501 Beautiful 5th Floor 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

$887

DESIGNER APARTMENT

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$86

Beachy "Margaritaville Pool home", 3 BR, 2 Bath

Clearwater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$488

Brightwater Blue 158-4 3 Floors of luxury with beautiful water views

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$5,200

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

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$201

Gulf Belleair Beach Condo 325 Condo located on Belleair Beach

Belleair Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$133

Stunning Waterfront Townhome With Private Rooftop Deck

Clearwater townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$259

Brightwater Point Condo 106 Amazing Water View Condo

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$563

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

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$121

THE VIEW IS AMAZING!!!!!

Hudson condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$155

Paradise on the Gulf of Mexico 1/1 6th floor condo

Hudson condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

All filters match

Price per night from

$104

Aqualea at Hyatt Regency, Clearwater Beach FL

Clearwater apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Match: Swimming pool

All filters match

Price per night from

$345

Condo Minutes From Clearwater Beach

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Swimming pool

All filters match

Price per night from

$172

Landmark Tower 1707 Charming 17th Floor Oceanfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$137

Match: Swimming pool

All filters match

Price per night from

$1,893

Memorial Day Getaway Savings

Clearwater house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 22

Match: Swimming pool

All filters match

Price per night from

$603

Home away from Home? Paradise in the Sun? Why not call it both! Pool now HEATED!

Tarpon Springs house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Swimming pool

All filters match

Price per night from

$259

NEW High End Keys Style - Private Resort - Huge Dock, Pool, Spa, + More

New Port Richey house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$345

Clearwater Vacation Beach 1B|R Condo fits 4ppl

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 28 minutes

Match: Swimming pool

All filters match

Price per night from

$138

Mandalay Beach Club 705P Beachfront - Mandalay Beach Club Condo

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$455

440 West Condos 1404-N 14th Floor Panoramic Water Views

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$377

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$160

Sereno Del Sol 213 Beach Access at Sereno Del Sol

Belleair Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$162

Harborview Grande 402 Panoramic 4th Floor Water View

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$256

Gorgeous Waterfront Grand Venezia Resort in Clearwater FL MLB Training

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Swimming pool

All filters match

Price per night from

$574

Crescent Beach Club 12E-N 12th Floor Beach Front Views

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$2,600

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$1,214

Mandalay Beach Club 706 SM Beachfront - Mandalay Beach Club Condo

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$6,429

Crescent Beach Club 9B Amazing 9th Floor Beach Front View

Belleair condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 50 minutes

Match: Swimming pool

All filters match

Price per night from

$5,200

Viewing 38 of 363
rentals in Holiday

×

Also consider