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Villas in Holiday

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Holiday villas

Exterior
Boho Villa B

Villa in Drew Park

Boho Villa B
10.0 out of 10, Exceptional, (1)
"It was a great location for the game but everything else was driving distance which we used uber. Communication was not as prompt as I was hoping and it always seemed a recording not a actual person very clean and cute thanks "
United States
Brenda C.
$199 nightly
The price is $223
Dec 21 - Dec 22
Total with taxes and fees
Boho Villa B
Exterior
Family villa w/ pool, fire pit & games

Villa in Clearwater

Family villa w/ pool, fire pit & games
10.0 out of 10, Exceptional, (1)
"This house was one of the most amazing houses I’ve ever stayed in. The house had everything for my friends and I too have a great time."
United States
Esean C.
$387 nightly
The price is $434
Dec 17 - Dec 18
Total with taxes and fees
Family villa w/ pool, fire pit & games
Outdoor dining
Wilderness Escape, by Breathtaking Natl Park

Villa in Town 'n' Country

Wilderness Escape, by Breathtaking Natl Park
8.6 out of 10, Excellent, (16)
"Great little house on the edge of the state park. It’s quiet and relaxing, but also less than a mile from any convenience you need. We would stay again. "
United States
Scott W.
$330 nightly
The price is $370
Jan 12 - Jan 13, 2026
Total with taxes and fees
Wilderness Escape, by Breathtaking Natl Park
Exterior
Boutique Stay: Near Beach, PSP4, Billiard or PingPong, Fire Pit, Private Yard

Villa in Park Lake Estates

Boutique Stay: Near Beach, PSP4, Billiard or PingPong, Fire Pit, Private Yard
9.0 out of 10, Wonderful, (4)
"The property was well maintained. We were comfortable. Location was close to restaurants, grocery stores, beaches etc…"
United States
Vicki E.
$141 nightly
The price is $155
Dec 23 - Dec 24
Total with taxes and fees
Boutique Stay: Near Beach, PSP4, Billiard or PingPong, Fire Pit, Private Yard
Exterior
Quite Paradise near Gulf of Mexico, Salt/Heated pool!!!!!,Port Richey

Villa in West Port

Quite Paradise near Gulf of Mexico, Salt/Heated pool!!!!!,Port Richey
9.6 out of 10, Exceptional, (46)
"Very nice enjoyed our stay."
United States
Brian B.
$324 nightly
The price is $358
Dec 17 - Dec 18
Total with taxes and fees
Quite Paradise near Gulf of Mexico, Salt/Heated pool!!!!!,Port Richey
Exterior
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles

Villa in Largo

2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
2.0 star property
10.0 out of 10, Exceptional, (21)
"My best friend and I had a wonderful birthday get away here with our friends!! "
United States
Rebecca A.
$486 nightly
The price is $543
Dec 17 - Dec 18
Total with taxes and fees
2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles
Exterior
Boho Villa A

Villa in Drew Park

Boho Villa A
10.0 out of 10, Exceptional, (1)
"THANK YOU."
United States
Babette R.
$219 nightly
The price is $246
Dec 19 - Dec 20
Total with taxes and fees
Boho Villa A
Exterior
Beach theme 2-bed villa WiFi in Palm Harbor HONEYMOON ISLAND Pinellas trail

Villa in Lake St. George

Beach theme 2-bed villa WiFi in Palm Harbor HONEYMOON ISLAND Pinellas trail
$292 nightly
The price is $326
Dec 17 - Dec 18
Total with taxes and fees
Beach theme 2-bed villa WiFi in Palm Harbor HONEYMOON ISLAND Pinellas trail
Exterior
Boho- Minimalist villa

Villa in Drew Park

Boho- Minimalist villa
9.0 out of 10, Wonderful, (4)
"Great location within walking distance to the stadium. Super clean and comfortable."
United States
Melissa
$244 nightly
The price is $274
Dec 21 - Dec 22
Total with taxes and fees
Boho- Minimalist villa
Exterior
Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa

Villa in Allen's Ridge

Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa
3.0 star property
$2,598 nightly
The price is $2,643
Dec 22 - Dec 23
Total with taxes and fees
Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa
Outdoor dining
Vacation Villa in Tampa 17 Guest

Villa in Town 'n' Country

Vacation Villa in Tampa 17 Guest
2.0 star property
$829 nightly
The price is $930
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Villa in Tampa 17 Guest
Exterior
NEW! Villa Valentino Luxury 8BR Villa with Heated Pool

Villa in Allen's Ridge

NEW! Villa Valentino Luxury 8BR Villa with Heated Pool
2.0 star property
$2,581 nightly
The price is $2,874
Dec 22 - Dec 23
Total with taxes and fees
NEW! Villa Valentino Luxury 8BR Villa with Heated Pool
Exterior
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Villa in Town 'n' Country

Sleeps 6 Hot Tub Fenced Yard Cozy Chic
3.0 star property
2.0 out of 10, (4)
"We were supposed to check in by 3 PM, but when we showed up at 5 PM the cleaners of the house were still there and we had to wait and sit and wait in the driveway until 6 PM until they were finished cleaning. The house smelled like smoke and marijuana and wasn’t the cleanest. "
United States
Joseph
$438 nightly
The price is $477
Dec 17 - Dec 18
Total with taxes and fees
Sleeps 6 Hot Tub Fenced Yard Cozy Chic
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

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"Great visit and the Wyndham delivered as usual. "
caroline 4-night trip
Posted 1 day ago
Wyndham Grand Clearwater Beach

Find out more about Holiday

Holiday Villas information

Number of reviews
95
Accommodation
93 Villas
Lowest Price
$155
Highest Price
$2,643

Frequently asked questions

How much do villas in Holiday cost?
Rates for villas in Holiday range between $155 and $2,643 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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