A forested area with a waterfall cascading over rocks.

Florida Holiday Rentals

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Our top choices for Florida holiday rentals

1. 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 NZ$799
includes taxes & fees
23 Sept - 24 Sept
The Greylock Cabin

2. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is NZ$465
includes taxes & fees
27 Aug - 28 Aug
Penthouse Apartment on Park Street

3. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is NZ$1,530
includes taxes & fees
6 Sept - 7 Sept
Riverbend Berkshire East Basecamp - 3 bedrooms available

4. Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,003
includes taxes & fees
30 Aug - 31 Aug
Bear Creek Cabin

5. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is NZ$510
includes taxes & fees
2 Sept - 3 Sept
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,569 reviews)
"Place was clean and well equipped, pool and amenities were great too !"
United States
Nyra
The price is NZ$181
includes taxes & fees
31 Aug - 1 Sept
Vacation Village in the Berkshires

7. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is NZ$802
includes taxes & fees
9 Sept - 10 Sept
A roomy remodeled retreat close to MassMoCA

8. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is NZ$2,167
includes taxes & fees
16 Sept - 17 Sept
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

9. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (17 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is NZ$484
includes taxes & fees
10 Sept - 11 Sept
2-Bdr Apt In Town, By the Water

10. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is NZ$461
includes taxes & fees
13 Sept - 14 Sept
New Studio In Town, By the Water

11. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.6 out of 10, Exceptional, (10 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is NZ$503
includes taxes & fees
15 Sept - 16 Sept
Downtown | Waterfront | Walk to Shops

12. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is NZ$339
includes taxes & fees
30 Aug - 31 Aug
Cozy Home in Pownal VT

13. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is NZ$322
includes taxes & fees
21 Sept - 22 Sept
Rose room Victorian home queen bed private bath

14. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is NZ$182
includes taxes & fees
8 Sept - 9 Sept
Huttopia Berkshires

15. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (62 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is NZ$337
includes taxes & fees
27 Aug - 28 Aug
Lovely 2nd Floor Apartment

16. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is NZ$841
includes taxes & fees
2 Sept - 3 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

17. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$353
includes taxes & fees
8 Sept - 9 Sept
Private bed with En-suite bathroom Marigold Room

18. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is NZ$530
includes taxes & fees
31 Aug - 1 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

19. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is NZ$592
includes taxes & fees
2 Sept - 3 Sept
Cozy private 2 bed apartment in Shelburne Falls

20. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
The price is NZ$399
includes taxes & fees
27 Aug - 28 Aug
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
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

Find out more about Florida

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Florida holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Florida. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Florida. Seeing all the best attractions is bound to make you fall in love with Florida. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Florida short-term rentals, that won’t be hard to do.

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?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Florida is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

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.