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Florida Holiday Rentals

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Florida holiday rentals

TV
Florida Mountain Log Cabin

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,592
HK$2,843 total
includes taxes & fees
4 Jan - 5 Jan 2026
Florida Mountain Log Cabin
Fridge, microwave, oven, stovetop
The Greylock Cabin

Holiday Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (5)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is HK$1,837
HK$3,099 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Greylock Cabin
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,575
HK$1,759 total
includes taxes & fees
4 Jan - 5 Jan 2026
Huttopia Berkshires
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
The price is HK$808
HK$988 total
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
Exterior
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is HK$462
HK$2,385 total
includes taxes & fees
4 Jan - 5 Jan 2026
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Interior
Lovely 2nd Floor Apartment

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is HK$903
HK$1,564 total
includes taxes & fees
27 Dec - 28 Dec
Lovely 2nd Floor Apartment
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,669
HK$1,865 total
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
9.0 out of 10, Wonderful, (4)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is HK$693
HK$1,860 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior detail
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,089
HK$2,369 total
includes taxes & fees
29 Dec - 30 Dec
Lake Whitingham & Mount Snow Area Village Apartment
Exterior detail
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Holiday Home in Hoosick Falls

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
9.8 out of 10, Exceptional, (100)
"Quiet and relaxing property "
United States
Michelle S.
The price is HK$903
HK$2,418 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is HK$902
HK$1,902 total
includes taxes & fees
2 Jan - 3 Jan 2026
Penthouse Apartment on Park Street
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is HK$778
HK$2,390 total
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Dining
Bright Boho Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

Bright Boho Apt in 18th c Berkshire Farmhouse
9.0 out of 10, Wonderful, (22)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is HK$1,127
HK$1,692 total
includes taxes & fees
28 Dec - 29 Dec
Bright Boho Apt in 18th c Berkshire Farmhouse
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,610
HK$3,691 total
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is HK$1,267
HK$3,552 total
includes taxes & fees
21 Jan - 22 Jan 2026
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Terrace/patio
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Chalet in Dover

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is HK$1,335
HK$3,952 total
includes taxes & fees
4 Jan - 5 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$957
HK$1,898 total
includes taxes & fees
3 Jan - 4 Jan 2026
Berkshires Apartment at the Stephentown Hotel
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is HK$599
HK$1,268 total
includes taxes & fees
28 Dec - 29 Dec
2 Twin beds on 1st floor with En-suite bathroom.
Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
The price is HK$1,516
HK$4,676 total
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Florida Hotel Reviews

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"A wonderful property with excellent amenities. The heated outdoor pool and sauna were clean and easily accessible. I travel with my small dog and my room was great. They actually upgraded me to a suite! I would stay here again without question. It is across the street from Mass MOCa, an extraordinary museum. Staff was courteous and helpful. "
Carleen 1-night trip
Posted 4 days ago
The Porches Inn at Mass MoCA

Find out more about Florida

Search for holiday rentals in Florida on Expedia! You can easily find your home rentals, villas, holiday apartments in Florida using one of the methods below:

  • View our selection of featured holiday rentals in Florida
  • Use the map to find apartments and other holiday homes in the Florida neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Florida while they last

Look no further and take a look at our great range of rental properties in Florida!

Frequently asked questions

Can I find holiday rentals in Florida?

Yes, there are holiday rentals close to the most popular sights in Florida, or you can select a more secluded option if you're looking for a relaxing stay. Florida is known for its forests.

What are some of the best holiday rentals that Florida has to offer?

The Greylock Cabin: This highly rated holiday home rental in Florida offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Florida?

Expedia has 3 holiday rentals for your stay in Florida.

What can I see and do in Florida?

Deerfield River and Green Mountain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, Hoosac Range and Florida Town Hall are other places worth a visit.

What are holiday rentals like in Florida?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Florida. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips.