A forested area with a waterfall cascading over rocks.

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Check availability on Florida Hotels with a Pool

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Florida hotels with a pool

An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A bookshelf with various books and pamphlets, including titles like 'JIMINY' and 'Berkshire Landscapes'.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A modern bathroom with a large mirror, two sinks, a toilet, and towel racks.

1. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
  • Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
₩158,000
₩176,486 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Downstreet, an Ascend Collection Hotel
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.

2. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
  • Float peacefully day or night at this 24-hour outdoor pool and hot tub sanctuary.
₩207,932
₩261,872 total
includes taxes & fees
Nov 22 - Nov 23
The Porches Inn at Mass MoCA
An indoor swimming pool with clear water, a diving area, and a view of the outdoors through large windows.
A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

3. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
Williamstown
  • Swim indoors year-round at this welcoming retreat with an indoor pool, hot tub, and extended pool hours for ultimate relaxation.
₩191,296
₩213,677 total
includes taxes & fees
Nov 16 - Nov 17
Fairfield Inn & Suites by Marriott Williamstown
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with a fireplace, comfortable seating, and large windows.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
₩106,493
₩133,493 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
A swimming pool with lounge chairs and a fence.
A breakfast buffet setup with cereal, milk, juice, and pastries.
A garden with a wooden pergola, potted plants, and a lawn with chairs.
A garden with a swing set, a blue chair, and a flower bed.

5. Maple Terrace Motel

Maple Terrace Motel
Williamstown
  • Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
₩131,225
₩146,574 total
includes taxes & fees
Nov 9 - Nov 10
Maple Terrace Motel
A rectangular swimming pool with a blue interior, surrounded by a white picket fence.
A hay bale display with pumpkins and scarecrows.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.
A white two-story building with a porch, labeled as a motel.

6. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
  • Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.
₩112,071
₩125,180 total
includes taxes & fees
Nov 8 - Nov 9
Willows Motel Williamstown
An outdoor seating area with Adirondack chairs and potted plants.
A sign with the word "CLARM" on a grassy field with a road and trees in the background.
A covered porch with beige siding, white railings, and a row of wooden benches.
A hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.

7. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
₩99,015
₩116,883 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Corner Motel
An indoor swimming pool with clear water, metal railings, and lounge chairs.
A hotel reception area with a reception desk, a chandelier, framed pictures, and a coffee station.
A Hampton Inn hotel with a covered entrance and a clear sign indicating a 16-foot clearance.
A hotel lobby with a fireplace, seating area, and a bar.

8. Hampton Inn Bennington

Hampton Inn Bennington
Bennington
  • Dive into year-round aquatic bliss at this Bennington retreat with an immaculate indoor pool and thoughtful amenities.
₩205,426
₩223,915 total
includes taxes & fees
Nov 3 - Nov 4
Hampton Inn Bennington
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A patio area with outdoor furniture, a fire pit, and potted plants.
A cozy living room with a stone fireplace, comfortable seating, and a television.
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

9. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
₩140,293
₩153,901 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
A blue building with a swimming pool, surrounded by trees and greenery.
A modern conference room with round tables and orange chairs, large windows with a view of greenery, and a ceiling with a grid pattern and hanging lights.
A hotel room with a large bed, a desk with a chair, a balcony with a view, and a TV mounted on the wall.
A tree with a fallen trunk in a grassy area with a blue building in the background.

10. Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham
Bennington
  • Soak up summer relaxation at this downtown hotel with a seasonal outdoor pool paradise.
₩130,694
₩142,456 total
includes taxes & fees
Nov 16 - Nov 17
Hotel Vervana, Trademark Collection by Wyndham
View all properties

Choose what matters most at hotels with a pool in Florida

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Florida Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"The rooms are outdated but they were clean. The hot tubs were down unfortunately which was one reason we booked this resort so that was a bummer but the staff was great and the price was right. The views were gorgeous and it's near hiking trails and a bike trail. Would book it again if they update their rooms and amenities."
Jennifer 1-night trip
Posted 1 hour ago
Jiminy Peak Mountain Resort
New Englander Inn Bennington

New Englander Inn Bennington

8/10 Good
"Nice place and nice people running it. Full breakfast included. Nice bed but a bit too soft for us. Nice shower."
Denise 1-night trip
Posted 8 hours ago
New Englander Inn Bennington
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Older but well-maintained property. Rooms were clean and nice."
John 1-night trip
Posted 1 day ago
Hotel Vervana, Trademark Collection by Wyndham
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Very well done remodel, clean and modern"
Brad 1-night trip
Posted 3 days ago
The Porches Inn at Mass MoCA
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"This was the perfect location and having modern amenities and snacks and breakfast was lovely."
Margaret 2-night trip
Posted 11 days ago
Hampton Inn & Suites Greenfield

Frequently asked questions

What are some accommodations with pools in Florida?
Blue Vista Motor Lodge: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Vacation Village in the Berkshires: Provides daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Hotel, 1-minute walk from Green Mountain National Forest. Provides daily, a seasonal outdoor pool, and free self parking. The Williams Inn: Hotel, 1-minute walk from Jiminy Peak Mountain Resort. Features 2 hot tubs, an outdoor pool, and 2 outdoor tennis courts. FairBridge Inn Express: Hotel, 1-minute walk from Green Mountain National Forest. Offers a sauna, a seasonal outdoor pool, and free self parking.
What is there to see and do in Florida?
The picturesque setting of Deerfield River and Green Mountain National Forest showcase the area's natural beauty. Discover sights such as Hoosac Range, Florida Town Hall, and Reed Brook Preserve during your stay.
When is the best time to book a hotel with a pool in Florida?
Taking into account the local weather in Florida is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Florida are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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