The Best Hotels with a Pool in Holiday, FL from ￥16,973 in 2026

Q: 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.

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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.

1. Fairfield Inn & Suites Holiday Tarpon Springs

Holiday

Dive into poolside paradise with premium loungers and sun-dappled waters at this serene hotel retreat.

￥19,009 total

includes taxes & fees

Nov 15 - Nov 16

A house with a swimming pool, outdoor seating, and a piano.

2. Family-Friendly Home w/Heated Pool Near Beaches

Holiday

￥74,354 total

includes taxes & fees

Nov 10 - Nov 11

A rectangular swimming pool with clear blue water, surrounded by a black fence.

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

Holiday

￥89,066 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a glass enclosure, outdoor seating, and a white building with large windows.

4. Canal‑Front Oasis w/Heated Pool Close to the Beach

Holiday Lake Estates

￥74,354 total

includes taxes & fees

Nov 10 - Nov 11

A covered outdoor seating area with a pool in the background.

5. Luxe Retreat | Pool, Fire Pit, Pet-Friendly Near Beaches | Sleeps 8

Holiday

￥75,400 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a tiled edge, surrounded by lounge chairs and a barbecue area, under a covered patio.

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

Holiday

￥41,921 total

includes taxes & fees

Nov 11 - Nov 12

A poolside view with a glass of drink, a covered seating area, and a view of the sunset over a body of water.

7. Lakefront Paradise, with Heated Private Pool.

Tahitian Development

Lakefront paradise offers families private pool enjoyment while viewing wildlife from the water.

￥70,092 total

includes taxes & fees

Nov 19 - Nov 20

A covered outdoor swimming pool with a slide, lounge chairs, and a patio area.

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

Holiday Lakes West

￥69,108 total

includes taxes & fees

Nov 16 - Nov 17

A poolside area with lounge chairs, a view of palm trees, and a clear sky.

9. Tropical Waterfront Oasis with Heated Pool & Private Fishing Dock: 3 bdrm 2 bths

Park Place

￥74,790 total

includes taxes & fees

Nov 20 - Nov 21

10. Waterfront Escape, Heated Pool, Private Dock, Gulf Access, near Island Beaches

Baileys Bluff Estates

￥86,492 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Choose what matters most at hotels with a pool in Holiday

Breakfast included

Hot tub

Top Holiday Hotel Reviews

Fairfield Inn & Suites Holiday Tarpon Springs

Holiday

10/10 Excellent

The stay was great and the room was spacious with a King size bed and a large bathroom. The area was quiet and easy to sleep. The breakfast in the morning was hot with a lot of options. There was plenty of parking and a great accommodating staff at the front desk both morning and night. It's in a great location and easy to get to as well.l The stay was great for the few days we were there. The only thing was the bed was made a little funky one day with a blanket being made over the bed and...

Paige

A swimming pool with a tiled deck, a building with a blue facade, and a clear sky.

Comfort Inn & Suites New Port Richey Downtown District

New Port Richey

10/10 Excellent

Hotel & room was clean!! Staff were friendly & great!! Staff seemed to enjoy their jobs. This was the best hotel we stayed at during our 2 week roadtrip. After our mishap at the beach, we were low in spirits. We got back to the hotel late at 11pm & we were so surprised to see our room had been cleaned. All the other hotels we stayed at you had to request for a cleaning service. They even put a mini Easter basket with treats in our room. I know to others this may not be much, but it lifted my...

Kayoua

A swimming pool with a water fountain, surrounded by palm trees and outdoor seating with umbrellas.

Holiday Inn Express & Suites Trinity by IHG

Trinity

10/10 Excellent

Anonymous traveler

A swimming pool area with lounge chairs and an umbrella, surrounded by a building with multiple windows and a tiled roof.

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

Downtown Dunedin

10/10 Excellent

Gary

A swimming pool with a brick patio, lounge chairs, and a white fence with signs.

Hampton Inn & Suites Tampa Northwest/Oldsmar

Oldsmar

10/10 Excellent

The staff was friendly, the room was clean and comfortable - AND quiet! The only thing I noticed that they may want to change is when the lobby restrooms are cleaned. Both days this was during breakfast, which is of course the busiest time. This also happened while our seminar was going on, which meant when we had a break, the only restroom available to us was out of order. Other than that, this was one of the best hotel stays I've had in a long time. Continental breakfast had ample...

Anonymous traveler

A hotel with a swimming pool, outdoor seating, and palm trees.

Quality Inn & Suites Tarpon Springs South

Tarpon Springs

10/10 Excellent

Jeanie

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

Wyndham Grand Clearwater Beach

Clearwater Beach

10/10 Excellent

Ernesto

A clear blue pool with a pool ladder, surrounded by lounge chairs and umbrellas, with a building in the background.

Holiday Inn Express & Suites Port Richey by IHG

Port Richey

10/10 Excellent

elbojpb

An outdoor swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a covered seating area.

Residence Inn Tampa Suncoast Parkway at NorthPointe Village

Lutz

10/10 Excellent

Beware DOG FRIENDLY...I don't travel with my dogs and didn't hear any here thanfully. It's a Very nice place NO PARKING FOR TRUCK WITH TRAILERS. Place is full I got the last room which is a condo practically very nice place. Bed is superb TV swivels so can watch on sofa or in the bed. Plush towels etc. It's $300 a night hotel not what I wanted to spend but it's all I could find. Nice place has fire pit outside can sit out with a fire.

Anonymous traveler

A pool area with a covered seating area, palm trees, and a building in the background.

Homewood Suites by Hilton Tampa - Port Richey

Port Richey

10/10 Excellent

Linda

A large outdoor swimming pool surrounded by lounge chairs and umbrellas, with a gazebo and a beach area.

Innisbrook Resort

Palm Harbor

10/10 Excellent

ray

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.

Find Hotels with a Pool in Holiday, FL

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Holiday hotels with a pool

1. Fairfield Inn & Suites Holiday Tarpon Springs

2. Family-Friendly Home w/Heated Pool Near Beaches

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

4. Canal‑Front Oasis w/Heated Pool Close to the Beach

5. Luxe Retreat | Pool, Fire Pit, Pet-Friendly Near Beaches | Sleeps 8

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

7. Lakefront Paradise, with Heated Private Pool.

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

9. Tropical Waterfront Oasis with Heated Pool & Private Fishing Dock: 3 bdrm 2 bths

10. Waterfront Escape, Heated Pool, Private Dock, Gulf Access, near Island Beaches

Choose what matters most at hotels with a pool in Holiday

Top Holiday Hotel Reviews

Fairfield Inn & Suites Holiday Tarpon Springs

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Holiday?

What is there to see and do in Holiday?

When is the best time to book a hotel with a pool in Holiday?