Best Villas in Holiday 2026

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Our top choices for Holiday villas

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

1. Villa IMPRESSA: Near Beach, Sleeps 6, Billiard/PingPong, Fire Pit, Private Yard

Park Lake Estates

Vicki E.

includes taxes & fees

16 Nov - 17 Nov

A covered entryway with a dark door, a small garden area with tropical plants, and a tiled floor.

2. Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

Oldsmar

Stephen W.

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a dining area, a refrigerator, and a painting on the wall.

3. 2-bedroom villa in tranquil Tampa with cool AC breeze

Carrollwood

Max r.

includes taxes & fees

30 Nov - 1 Dec

An outdoor wooden table with chairs and a large umbrella.

4. Wilderness Escape, by Breathtaking Natl Park

Town 'n' Country

Julie D.

includes taxes & fees

18 Nov - 19 Nov

A covered patio area with a table and chairs, a grill, and views of a red barn and a white house.

5. The Flo's house, Snowbird Winter Haven • Spacious 1800 sq ft Home with New Lanai

Lake Magdalene

includes taxes & fees

9 Nov - 10 Nov

A large green building with a covered patio area, a pool, and a waterfront view.

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

Town 'n' Country

Melinda B.

includes taxes & fees

22 Nov - 23 Nov

A covered outdoor area with wicker furniture, a pool, and a view of a lake and palm trees.

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

Clearwater

A R.

includes taxes & fees

11 Nov - 12 Nov

A single-story house with a garage, a well-maintained lawn, and a clear sky.

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

Clearwater

includes taxes & fees

14 Nov - 15 Nov

An outdoor pool area with a covered patio, bar stools, and Adirondack chairs.

9. 2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles

Largo

Jason D.

includes taxes & fees

8 Nov - 9 Nov

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Learn more about Holiday

Nestled along the Gulf Coast, this relaxed town offers pristine beaches and the stunning Anclote River Park for kayaking adventures. Locals recommend exploring the Suncoast Trail by bike and timing your visit to Holiday's lively seasonal festivals where seafood is always the star.

See all hotels in Holiday

A calm lake with a dock, a boat, and a building surrounded by trees.

Top reviews in Holiday

Outdoor patio furniture with metal chairs and a table, surrounded by a metal fence.

Fairfield Inn & Suites Holiday Tarpon Springs

Holiday

10/10 Excellent

Kevin

A balcony with a white sofa, a small table with drinks, and a potted plant.

Ivory Sands Beach Suites

Clearwater Beach

10/10 Excellent

sandra

A modern hotel with a prominent 'Comfort Inn & Suites' sign, a well-lit entrance, and a landscaped area with a small pool.

Comfort Inn & Suites New Port Richey Downtown District

New Port Richey

10/10 Excellent

This is a newer Comfort Inn and the room was well laid out with plenty of room for luggage. Additionally :black out blinds, a night light in the bathroom, microwave and small fridge meant that it was well equipped. The beds were comfy and the shower/bath worked well, although it could have been hotter! Breakfast was sausages, French toast, scrambled eggs and make your own waffles. Also there were pastries, muffins, cereal, oatmeal, toast, yoghurt and fruit. The breakfast area is larger and not...

Diana

A Hampton Inn & Suites hotel with a modern design, featuring multiple floors and a well-lit facade.

Hampton Inn & Suites Tarpon Springs

Tarpon Springs

10/10 Excellent

Daniel

A residential area with a house featuring a red-tiled roof, a driveway with parked cars, and a well-maintained lawn with palm trees.

Devon Shores

Clearwater Beach

10/10 Excellent

Another excellent stay at Devon Shores. I’ve stayed at a few hotels on Clearwater Beach, most high end ones and since discovering Devon Shores I won’t go anywhere else. The staff, facilities and cleanliness are all fantastic. Parking is included, beach/pool towels are included, coffee/tea is included, plenty toiletries are included, even the little touches like umbrellas available if needed are super appreciated.

Hayley

A modern hotel with a prominent sign, a covered entrance, and a well-maintained lawn.

Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

Oldsmar

10/10 Excellent

Andrew

A waterfront hotel with multiple floors, balconies, and a marina with boats.

ChartHouse Clearwater Beach Marina Hotel

Clearwater Beach

10/10 Excellent

Hotel is a great location, and extremely clean! We were on 8th floor, over looking marina which was great! We could see all the tour boats go in and out and even watch the dolphins! It was our tenth anniversary and the hotel put me in contact with a local balloon display company who they used themselves when they opened (Bubbly Balloons) who went in and decorated our room before we arrived. Highly recommend this hotel.

Ambet

A multi-story hotel with a swimming pool, a fenced area, and a clear view of the sky.

The J Hotel Dunedin near Honeymoon Island State Park, an Ascend Collection Hotel

Causeway

10/10 Excellent

Matt

A hotel exterior with a stone facade, large windows, and an outdoor seating area with orange cushions.

Hilton Garden Inn Tampa Suncoast Parkway

Lutz

8/10 Good

Geoffrey

An outdoor patio area with green chairs, a round table, and a built-in seating area with a fire pit.

SpringHill Suites by Marriott Tampa Suncoast Parkway

Land O' Lakes

10/10 Excellent

Robert

A multi-story hotel with a covered entrance, outdoor seating area, and a staircase leading to the upper levels.

The Grant Street Inn Dunedin Downtown Historic District, an Ascend Collection Hotel

Downtown Dunedin

10/10 Excellent

Philip

A hotel with a central courtyard, palm trees, and a well-lit entrance.

Holiday Inn Express Hotel & Suites Clearwater North-Dunedin by IHG

Downtown Dunedin

10/10 Excellent

Jemma

Frequently Asked Questions

How much do villas in Holiday cost?

Rates for villas in Holiday range between £163 and £941 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. Holidaying 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 accommodation 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.

Search Villas in Holiday

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Holiday villas

1. Villa IMPRESSA: Near Beach, Sleeps 6, Billiard/PingPong, Fire Pit, Private Yard

2. Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

3. 2-bedroom villa in tranquil Tampa with cool AC breeze

4. Wilderness Escape, by Breathtaking Natl Park

5. The Flo's house, Snowbird Winter Haven • Spacious 1800 sq ft Home with New Lanai

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

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

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

9. 2,100sqf Villa · KING Beds · Heated Pool · Game Room · GYM · Beach 2miles

Learn more about Holiday

Top reviews in Holiday

Fairfield Inn & Suites Holiday Tarpon Springs

10/10 Excellent

Frequently Asked Questions

How much do villas in Holiday cost?

Why book your villa in Holiday with Expedia?

How can I find cheap villas in Holiday?

What is there to do near my villa in Holiday?

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