A forested area with a waterfall cascading over rocks.

Florida Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Florida holiday rentals

Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is HK$1,853
HK$3,209 total
includes taxes & fees
21 Jul - 22 Jul
The Greylock Cabin
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$946
HK$1,056 total
includes taxes & fees
30 Jun - 1 Jul
Huttopia Berkshires
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,410 reviews)
"Property is great and stay was great"
United States
Isha
The price is HK$975
HK$1,175 total
includes taxes & fees
21 Jul - 22 Jul
Vacation Village in the Berkshires
Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is HK$1,372
HK$3,409 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (58 reviews)
"Very clean and cozy apartment. "
United States
Kim G.
The price is HK$910
HK$1,595 total
includes taxes & fees
30 Jun - 1 Jul
Lovely 2nd Floor Apartment
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$534
HK$2,561 total
includes taxes & fees
5 Jul - 6 Jul
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is HK$2,290
HK$5,387 total
includes taxes & fees
29 Jun - 30 Jun
5BR Berkshire Home Mins To The Mountain
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is HK$855
HK$1,069 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,137
HK$4,695 total
includes taxes & fees
6 Jul - 7 Jul
Bear Creek Cabin
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
The price is HK$1,035
HK$3,563 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$1,482
HK$3,548 total
includes taxes & fees
30 Jun - 1 Jul
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Terrace/patio

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (33 reviews)
"Great place"
United States
Aidan K.
The price is HK$776
HK$1,941 total
includes taxes & fees
30 Jun - 1 Jul
Peaceful getaway at birds of a feather
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
United States
Karissa A.
The price is HK$1,490
HK$3,171 total
includes taxes & fees
21 Jul - 22 Jul
Perfect for a peaceful get away in clean fresh Vermont air!
Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is HK$2,980
HK$5,125 total
includes taxes & fees
29 Jun - 30 Jun
3 Mi to Mount Snow: Spacious West Dover Home
Fridge, microwave, oven, stovetop

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is HK$3,635
HK$9,061 total
includes taxes & fees
29 Jun - 30 Jun
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Exterior

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is HK$1,561
HK$3,228 total
includes taxes & fees
3 Jul - 4 Jul
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, stovetop, dishwasher

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (6 reviews)
"Gorgeous views even in March, ample heating/cooling, wonderful host experience, would just recommend bringing paper plates/utensils as we found ourselves running the dishwasher often. "
United States
avery o.
The price is HK$3,795
HK$6,368 total
includes taxes & fees
12 Jul - 13 Jul
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$2,157
HK$2,676 total
includes taxes & fees
29 Jun - 30 Jun
Vikings Villages Resort - Double Bed Room
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is HK$1,270
HK$2,383 total
includes taxes & fees
6 Jul - 7 Jul
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Living area

Green Mountain Getaway

Green Mountain Getaway
Bennington
9.6 out of 10, Exceptional, (18 reviews)
"Very clean property. The location was very convenient to the Main Street of Bennington. Easy check in process. Would definitely stay here again! "
United States
Meredith Y.
The price is HK$1,615
HK$3,210 total
includes taxes & fees
29 Jun - 30 Jun
Green Mountain Getaway
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

Berkshire Inn

Berkshire Inn

8/10 Good
"Clean room, nice staff, only complaint was curtains were long which hung over ac and was annoying."
Anthony 1-night trip
Posted 13 hours ago
Berkshire Inn

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?

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts: This holiday home rental outside of Florida is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a selection of games.

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.