A beach with people standing and facing the ocean, with their arms raised. There are two suitcases on the sand.

Villas in Holiday

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  • Upfront pricing

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Holiday villas

A single-story house with a garage and a front yard.

1. Boutique Stay: Near Beach, PSP4, Billiard or PingPong, Fire Pit, Private Yard

Boutique Stay: Near Beach, PSP4, Billiard or PingPong, Fire Pit, Private Yard
Park Lake Estates
9.2 out of 10, Wonderful, (5 reviews)
"The property was well maintained. We were comfortable. Location was close to restaurants, grocery stores, beaches etc…"
United States
Vicki E.
$208 nightly
The price is $230
Sep 28 - Sep 29
Total with taxes and fees
Boutique Stay: Near Beach, PSP4, Billiard or PingPong, Fire Pit, Private Yard
An outdoor wooden table with chairs and a large umbrella.

2. Wilderness Escape, by Breathtaking Natl Park

Wilderness Escape, by Breathtaking Natl Park
Town 'n' Country
9.0 out of 10, Wonderful, (28 reviews)
"Comfy beds. Clean and roomy."
United States
Julie D.
$245 nightly
The price is $275
Sep 28 - Sep 29
Total with taxes and fees
Wilderness Escape, by Breathtaking Natl Park
A large green building with a covered patio area, a pool, and a waterfront view.

3. Sleeps 40! 13BR•Heated Pool•Waterfront Resort•Spa

Sleeps 40! 13BR•Heated Pool•Waterfront Resort•Spa
Town 'n' Country
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful price! Great location! HUGE! You feel like you’re in the middle of nowhere but close to everything in the city. Definitely a retreat location."
United States
Melinda B.
$898 nightly
The price is $1,011
Sep 30 - Oct 1
Total with taxes and fees
Sleeps 40! 13BR•Heated Pool•Waterfront Resort•Spa
An aerial view of a swimming pool with lounge chairs and a covered area with a striped roof.

4. Relaxing home Mini-Golf/ heated pool 2/2

Relaxing home Mini-Golf/ heated pool 2/2
Largo
10.0 out of 10, Exceptional, (3 reviews)
"Zarko went above and beyond to accommodate our requests. We really enjoyed the heated pool after a day at the ball diamond. The beds were comfortable and the kitchen was well equipped. I would stay here again if we were in Clearwater Beach or the surrounding area. Thanks again Zarko for an amazing stay. "
Canada
Kim M.
$321 nightly
The price is $361
Sep 29 - Sep 30
Total with taxes and fees
Relaxing home Mini-Golf/ heated pool 2/2
A single-story house with a garage, a well-maintained lawn, and a clear sky.

5. Heated Pool~Spa~Mini Golf~Fire Pit~Game Room

Heated Pool~Spa~Mini Golf~Fire Pit~Game Room
Clearwater
$609 nightly
The price is $685
Sep 28 - Sep 29
Total with taxes and fees
Heated Pool~Spa~Mini Golf~Fire Pit~Game Room
A single-story house with a beige exterior, a front door, and a satellite dish.

6. Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic
3.0 star property
Town 'n' Country
2.0 out of 10, (6 reviews)
"This place was double booked. I never received any type of communication from the property then had to find a place to stay because I wasn’t told it was double booked until I showed up and there was people already in the house. I do NOT recommend this place. "
United States
Savanah
$352 nightly
The price is $379
Sep 28 - Sep 29
Total with taxes and fees
Sleeps 6 Hot Tub Fenced Yard Cozy Chic
A poolside bar area with a clear view of a swimming pool, lounge chairs, and a tropical landscape.

7. The Belleair Estate - Breathtaking Waterfront Home w/ Heated Pool

The Belleair Estate - Breathtaking Waterfront Home w/ Heated Pool
Clearwater
9.6 out of 10, Exceptional, (55 reviews)
"Great stay"
United States
A R.
$942 nightly
The price is $1,054
Sep 28 - Sep 29
Total with taxes and fees
The Belleair Estate - Breathtaking Waterfront Home w/ Heated Pool
An outdoor pool area with a covered patio, bar stools, and Adirondack chairs.

8. 2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles

2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Largo
10.0 out of 10, Exceptional, (41 reviews)
"Wonderful property. We had an outstanding time staying here. We especially liked that it was close to grocery, food , and other retail locations."
United States
Michael D.
$553 nightly
The price is $620
Oct 27 - Oct 28
Total with taxes and fees
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Holiday Hotel Reviews

Sailport Waterfront Suites

Sailport Waterfront Suites

10/10 Excellent
"We had a great stay!! Everything was perfect!! Recommend to my friends and family 100 %"
Lanora 1-night trip
Posted 10 hours ago
Sailport Waterfront Suites

Find out more about Holiday

Holiday Villas information

Number of reviews
82
Accommodation
86 Villas
Lowest Price
$230
Highest Price
$1,054

Frequently asked questions

How much do villas in Holiday cost?
Rates for villas in Holiday range between $230 and $1,054 per night. Whatever your budget, you'll find a place that fits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your villa in Holiday with Expedia?
Expedia makes it easy to find your ideal villa in Holiday. Vacationing with the kids? Use our helpful filters to search for stays with amenities like a pool. If you have a certain budget, choose how much you want to spend and the star rating of the property. We'll help you find the right stay that suits your style and taste.
How can I find cheap villas in Holiday?
With Expedia's user-friendly filter tool, locating cheap villas in Holiday is easy. To find accommodations that are gentle on your bank balance, narrow your search by star rating, amenities and budget.
What is there to do near my villa in Holiday?
The ideal travel accessory is a well-planned schedule. Anclote River Park is a top place to start your sightseeing in Holiday.

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