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

Find Hotels with a Pool in Holiday, FL from CA $137

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Check availability on Holiday Hotels with a Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Holiday hotels with a pool

A swimming pool with a no diving sign, lounge chairs, and a lifeguard on duty sign.
Room
A hotel dining area with multiple tables and chairs, a counter with food and beverage options, and large windows providing natural light.
A hotel room with a large bed, two bedside lamps, a wooden nightstand, a desk, and a chair.

1. Fairfield Inn & Suites Holiday Tarpon Springs

Fairfield Inn & Suites Holiday Tarpon Springs
Holiday
  • Dive into poolside paradise with premium loungers and sun-dappled waters at this serene hotel retreat.
CA $151
CA $170 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites Holiday Tarpon Springs
A backyard with a swimming pool, lounge chairs, and a patio area.
A modern living room with a blue sofa, a flat-screen TV mounted on the wall, and a decorative vase with dried flowers.
A kitchen with wooden cabinets, a stainless steel microwave, a toaster, a stove, and a refrigerator.
A modern living room with a flat-screen TV, a dining area with chairs, and a large window.

2. Sunny Oasis by Tarpon - Heated Pool, Hot Tub & Playground

Sunny Oasis by Tarpon - Heated Pool, Hot Tub & Playground
Holiday
CA $185
CA $377 total
includes taxes & fees
Nov 16 - Nov 17
Sunny Oasis by Tarpon - Heated Pool, Hot Tub & Playground
A poolside view with a glass of drink, a covered seating area, and a view of the sunset over a body of water.
A modern living room with a sectional sofa, a small round table, and a bar area with stools.
A fire pit with two Adirondack chairs, a stone fire surround, and a view of a body of water with lights in the background.
Private kitchen

3. Lakefront Paradise, with Heated Private Pool.

Lakefront Paradise, with Heated Private Pool.
Tahitian Development
  • Lakefront paradise offers families private pool enjoyment while viewing wildlife from the water.
CA $243
CA $609 total
includes taxes & fees
Oct 26 - Oct 27
Lakefront Paradise, with Heated Private Pool.
A rectangular swimming pool with clear blue water, surrounded by a black fence.
A lifeguard tower with a flat roof, multiple windows, and a metal railing.
A beach with umbrellas, beach chairs, and people swimming in the water.
A hammock on a wooden deck overlooking a lake with houses in the background.

4. GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!

GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!
Holiday
CA $248
CA $752 total
includes taxes & fees
Oct 18 - Oct 19
GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!
A covered outdoor swimming pool with a slide, lounge chairs, and a patio area.
A bedroom with a bed, a nightstand, a dresser, a ceiling fan, and a sliding glass door leading to a pool area.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.
A modern kitchen with white cabinets, a central island with bar stools, a ceiling fan, pendant lights, and a large window with blinds.

5. Coastal Family Retreat – Heated Pool, Fire Pit & Fun!

Coastal Family Retreat – Heated Pool, Fire Pit & Fun!
Holiday Lakes West
CA $227
CA $624 total
includes taxes & fees
Oct 22 - Oct 23
Coastal Family Retreat – Heated Pool, Fire Pit & Fun!
A covered outdoor seating area with a pool in the background.
A kitchen with granite countertops, a stainless steel sink, and a coffee station.
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.
A modern kitchen with white cabinets, a granite countertop, and a built-in microwave. There are two brown chairs and a small table with decorative items.

6. Luxe Retreat with Resort-Style Backyard w/Heated Pool • Fire Pit • Near Beaches

Luxe Retreat with Resort-Style Backyard w/Heated Pool • Fire Pit • Near Beaches
Holiday
CA $251
CA $688 total
includes taxes & fees
Oct 20 - Oct 21
Luxe Retreat with Resort-Style Backyard w/Heated Pool • Fire Pit • Near Beaches
A swimming pool with a glass enclosure, outdoor seating, and a white building with large windows.
A dining area with a table and chairs, large windows, and a view of a swimming pool.
A modern kitchen with white cabinetry, stainless steel appliances, and a coffee maker.
A dining area with a dark wooden table, four upholstered chairs, and a vase with red flowers.

7. Cozy Canal-Front Getaway•Heated Pool•Relaxation•Fishing•Beaches Nearby

Cozy Canal-Front Getaway•Heated Pool•Relaxation•Fishing•Beaches Nearby
Holiday Lake Estates
CA $252
CA $684 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Canal-Front Getaway•Heated Pool•Relaxation•Fishing•Beaches Nearby
A swimming pool with a tiled deck, a building with a blue facade, and a clear sky.
A modern kitchen with a central island, a dining area with yellow chairs, and a living space with a blue sofa.
A modern reception area with a wooden panel wall, a crescent moon design, and a counter with computers.
A hotel room with a large bed, a wooden nightstand, a desk, and a chair. There is a window with curtains, a wall-mounted lamp, and a patterned wall.

8. Comfort Inn & Suites New Port Richey Downtown District

Comfort Inn & Suites New Port Richey Downtown District
New Port Richey
  • Escape to a sparkling oasis at this downtown hotel with a refreshing outdoor pool experience.
CA $123
CA $137 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites New Port Richey Downtown District
A pool area with a pathway leading to a building, surrounded by potted plants and palm trees.
A Hampton Inn & Suites hotel with a modern design, featuring multiple floors and a well-lit facade.
A hotel room with a flat-screen TV, a desk, a chair, a sofa, and a window with curtains.
A gazebo with a view of the water, surrounded by palm trees.

9. Hampton Inn & Suites Tarpon Springs

Hampton Inn & Suites Tarpon Springs
Tarpon Springs
  • Dive into poolside paradise with sunny Florida skies and Gulf breezes at this refreshing Tarpon Springs retreat.
CA $156
CA $176 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Tarpon Springs
A hotel with a swimming pool, outdoor seating, and palm trees.
A bar area with wooden chairs, a counter with bottles, and a TV mounted on the wall.
A hotel room with a bed, a desk with a television, a chair, a nightstand with a lamp, and a view of the outdoors through the window.
A lobby with a leather sofa, two armchairs, a wooden coffee table, and two lamps.

10. Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South
Tarpon Springs
  • Soak up the sun at this tranquil hotel pool retreat with comfortable lounge chairs and beautiful landscaped gardens.
CA $113
CA $128 total
includes taxes & fees
Oct 25 - Oct 26
Quality Inn & Suites Tarpon Springs South
View all properties

Choose what matters most at hotels with a pool in Holiday

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Holiday Hotel Reviews

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"Excellent visit aside from the Club Wyndham sales people constantly pestering you every single time you leave to tour the "club" side for a free 1 week vacation to any destination of your choice"
James 4-night trip
Posted 1 hour ago
Wyndham Grand Clearwater Beach
Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

10/10 Excellent
"This hotel was great. Clean, helpful staff, decent breakfast spread and very close to the beach! The area feels safe, lots of people walking and it’s walking distance to the Main Street where all the restaurants are. We enjoyed staying here and I appreciate the fact that the hotel rooms were not outdated and everything was in great shape. I’ve had a bad experience recently with another hotel chain, and was hesitant with my stay here; but thankfully I am satisfied and would return to this hotel if I’m ever in Clearwater again."
Fabiana 4-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott Clearwater Beach
Gulfview Hotel on the Beach

Gulfview Hotel on the Beach

8/10 Good
"What a great hidden gem! I am so glad that I gave them a shot. The pool and hot tub were clean, as well as the rest of the grounds. There is direct Beach Access, Super Clean Property. This is an older property and if you look hard you will see a little maintenance needed here and there, but it was immaculately clean and the staff was fabulous. We were greeted with a big smile and pleasant conversation every time we came and went! Our room had a beach view and a great little balcony that you could watch the sunrise/sunset from! I would definitely stay here again."
Susan 3-night trip
Posted 3 hours ago
Gulfview Hotel on the Beach
Hyatt Regency Clearwater Beach Resort and Suites

Hyatt Regency Clearwater Beach Resort and Suites

10/10 Excellent
"We had a great stay"
Karine 4-night trip
Posted 6 hours ago
Hyatt Regency Clearwater Beach Resort and Suites
Opal Sands Resort

Opal Sands Resort

10/10 Excellent
"This hotel was absolutely gorgeous! Located right near pier 60. It had a beautiful pool and hot tub, Beach access, Beach bar, Restaurants. The rooms were amazing with balconies over looking the ocean. We had a great time and will deff be back!"
Julia 2-night trip
Posted 9 hours ago
Opal Sands Resort
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

8/10 Good
"The beach chairs cost to much and the guys took your chair even if your had a towel on it"
William 2-night trip
Posted 9 hours ago
Hilton Clearwater Beach Resort & Spa
Shephard's Beach Resort

Shephard's Beach Resort

10/10 Excellent
"Tons of Activities, close to private beach access and walking distance to shops and public access beach."
Erica 2-night trip
Posted 13 hours ago
Shephard's Beach Resort
DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

10/10 Excellent
"wonderful very clean great staff and great restaurant"
Cynthia 1-night trip
Posted 2 days ago
DoubleTree by Hilton Tampa Rocky Point Waterfront
Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

10/10 Excellent
"We had an adventure. Our original hotel had a fire and we were forced to find different accommodations that evening. Our hostess found us a room at your hotel and took care us. We enjoyed the hot tub, pool and beach area. It was great. Thank you again for taking such great care of us."
Anonymous traveller 2-night trip
Posted 3 days ago
Pelican Pointe Clearwater Beach Hotel

Frequently asked questions

What are some accommodations with pools in Holiday?
Wyndham Grand Clearwater Beach: Hotel, 2-minute walk from Pier 60 Park. Features 3 restaurants, an outdoor pool, and a full-service spa. Hyatt Regency Clearwater Beach Resort and Suites: Resort, 3-minute walk from St. Petersburg - Clearwater Beaches. Offers a children's pool, an outdoor pool, and 2 restaurants. Hilton Clearwater Beach Resort & Spa: Resort, 1-minute walk from Pier 60 Park. Provides a private beach, 2 outdoor pools, and 3 restaurants. Fairfield Inn & Suites by Marriott Clearwater Beach: Hotel, 3-minute walk from St. Petersburg - Clearwater Beaches. Features daily, an outdoor pool, and complimentary wireless internet access. The Westin Tampa Bay: Hotel, 8-minute walk from Tampa Bay. Offers a private beach, an outdoor pool, and complimentary bicycles.
What is there to see and do in Holiday?
The picturesque setting of Anclote River Park and Lake Conley showcase the area's natural beauty. Discover sights such as Key Vista Nature Park during your stay. You'll also discover lots of options for restaurants in Holiday.
When is the best time to book a hotel with a pool in Holiday?
Taking into account the local weather in Holiday is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 64°F. Average annual precipitation for Holiday is 42 inches.

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