A forested area with a waterfall cascading over rocks.

Find Hotels with a Pool in Florida, MA from CA $126

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Florida Hotels with a Pool

Tonight
Oct 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern interior with a large window, a wooden table, and bar stools.
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.
CA $170
CA $190 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Downstreet, an Ascend Collection Hotel
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A hallway with a collection of plates on the walls, leading to a staircase.
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."

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.
CA $212
CA $268 total
includes taxes & fees
Nov 10 - Nov 11
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 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.
A fire feature with a metal frame and a brick wall in the background.

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.
CA $212
CA $237 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Williamstown
A rectangular swimming pool with a blue interior, surrounded by a white picket fence.
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
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.

4. 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.
CA $121
CA $135 total
includes taxes & fees
Nov 1 - Nov 2
Willows Motel Williamstown
A swimming pool with lounge chairs and a fence.
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.
A breakfast buffet setup with cereal, milk, juice, and pastries.

5. Maple Terrace Motel

Maple Terrace Motel
Williamstown
  • Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
CA $141
CA $158 total
includes taxes & fees
Nov 1 - Nov 2
Maple Terrace Motel
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 hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

6. Cozy Corner Motel

Cozy Corner Motel
Williamstown
  • Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.
CA $107
CA $126 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Corner Motel
Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

7. 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.
CA $115
CA $144 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A poolside area with lounge chairs, umbrellas, and a swimming pool.
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.
A patio area with outdoor furniture, a fire pit, and potted plants.

8. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
CA $151
CA $165 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.
A hotel lobby with a reception desk, seating area with sofas and armchairs, a stone fireplace, and a television mounted on the wall.
A wooden cabin with a porch and steps leading to a door, surrounded by snow.

9. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
  • Ski-in/ski-out mountain resort with refreshing pool, hot tubs, and tennis courts awaits.
CA $191
CA $214 total
includes taxes & fees
Oct 18 - Oct 19
Jiminy Peak Mountain Resort
A blue building with a swimming pool, surrounded by trees and greenery.
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 hotel room with a red sofa, a round wooden table, a black armchair, a bed, and a large window with a view of 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.

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.
CA $150
CA $164 total
includes taxes & fees
Nov 1 - Nov 2
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

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"This Best Western was very quiet and clean even though it was close to the airport! The restaurant and staff were excellent! I was stay here again! The pool and gym were very well kept and clean!"
Chris 2-night trip
Posted less than an hour ago
Hotel Vervana, Trademark Collection by Wyndham
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is my go-to accommodation to visit Williams College in Williamstown."
David 1-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
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 14 hours ago
Hampton Inn & Suites Greenfield
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Good location, nice and clean rooms, exceptional breakfast."
Adrian 2-night trip
Posted 17 hours ago
Willows Motel Williamstown
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 22 hours ago
Jiminy Peak Mountain Resort

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.

Explore a world of travel with Expedia