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Florida Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Florida vacation rentals

A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

1. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
$415 nightly
The price is $451
Dec 8 - Dec 9
Total with taxes and fees
Greylock Cabin
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

2. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
$169 nightly
The price is $189
Nov 9 - Nov 10
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

3. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 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.
$233 nightly
The price is $260
Nov 8 - Nov 9
Total with taxes and fees
Penthouse Apartment on Park Street
A log cabin with a balcony, surrounded by trees.

4. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
$497 nightly
The price is $555
Nov 12 - Nov 13
Total with taxes and fees
Bear Creek Cabin
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

5. 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.
$1,090 nightly
The price is $1,218
Nov 16 - Nov 17
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Indoor pool

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,833 reviews)
"Great resort, great location very spacious."
United States
Marcos
$122 nightly
The price is $136
Dec 8 - Dec 9
Total with taxes and fees
Vacation Village in the Berkshires
A kitchen with white cabinets, a wooden dining table, and pendant lights.

7. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
$420 nightly
The price is $469
Nov 10 - Nov 11
Total with taxes and fees
A roomy remodeled retreat close to MassMoCA
"The property comes equipped with everything one can need for a relaxing getaway, not to mention a fire pit in the backyard nested on top of a river. It’s truly relaxing and peaceful while still being close to restaurants and a super market." ...Anna

8. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (21 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$241 nightly
The price is $271
Nov 15 - Nov 16
Total with taxes and fees
New Studio In Town, By the Water
Private kitchen

9. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
$264 nightly
The price is $298
Nov 15 - Nov 16
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
"We had a lovely week-long stay at this cozy spot by the river. We cook a lot when we visit Airbnbs and we were so thrilled to find a huge variety of cooking pots, pans, utensils, etc. " ...Patrick

10. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (22 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
$252 nightly
The price is $284
Nov 8 - Nov 9
Total with taxes and fees
2-Bdr Apt In Town, By the Water
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

11. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
$174 nightly
The price is $195
Nov 8 - Nov 9
Total with taxes and fees
Cozy Home in Pownal VT
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

12. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
$858 nightly
The price is $958
Nov 20 - Nov 21
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

13. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$149 nightly
The price is $166
Nov 8 - Nov 9
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A cozy living room with a large window, wooden walls, and a television.

14. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
$185 nightly
The price is $207
Nov 8 - Nov 9
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A cozy living room with a fireplace, leather sofa, and a television.

15. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
$185 nightly
The price is $207
Nov 8 - Nov 9
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

16. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
$185 nightly
The price is $207
Nov 8 - Nov 9
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A wooden deck with a railing, a house with windows, and a forested area with a stream.

17. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
$540 nightly
The price is $603
Nov 8 - Nov 9
Total with taxes and fees
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

18. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
$172 nightly
The price is $192
Nov 8 - Nov 9
Total with taxes and fees
Private room with En-suite bathroom Marigold Room
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

19. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
$487 nightly
The price is $520
Nov 23 - Nov 24
Total with taxes and fees
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

20. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
$443 nightly
The price is $500
Nov 9 - Nov 10
Total with taxes and fees
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
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

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams

10/10 Excellent

Great place!
United States
Ann
Reviewed May 12, 2025
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Florida

Everything you need to know about Florida vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Florida vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Florida vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Florida vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Florida. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Florida in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Florida rentals

At Expedia, we put the best Florida vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Florida rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Florida vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Florida. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Florida?

Yes, we give you a choice of vacation rentals close to popular local attractions in Florida, or you can select a secluded option if you're looking for relaxation. Florida is known for its forests.

What are some of the best vacation rentals in Florida?

Experience Three Sisters Sanctuary in Goshen, MA: Visitors like this Florida vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Florida?

Expedia has 3 vacation 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 vacation rentals like in Florida?

Vacation rentals are privately owned properties you can book for a short or long stay in Florida. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips.

Explore a world of travel with Expedia