A forested area with a waterfall cascading over rocks.

Florida Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Florida holiday rentals

A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

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.
The price is NZ$815
includes taxes & fees
8 Nov - 9 Nov
Greylock Cabin
A two-story blue house with a porch, surrounded by a garden with orange flowers.

2. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is NZ$263
includes taxes & fees
14 Oct - 15 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
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.

3. 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.
The price is NZ$397
includes taxes & fees
14 Oct - 15 Oct
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.

4. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.8 out of 10, Exceptional, (16 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$495
includes taxes & fees
18 Oct - 19 Oct
Penthouse Apartment on Park Street
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

5. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,722 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is NZ$179
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A log cabin with a balcony, surrounded by trees.

6. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,072
includes taxes & fees
15 Oct - 16 Oct
Bear Creek Cabin
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

7. 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$2,226
includes taxes & fees
2 Nov - 3 Nov
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A kitchen with white cabinets, a wooden dining table, and pendant lights.

8. 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
The price is NZ$838
includes taxes & fees
13 Oct - 14 Oct
A roomy remodeled retreat close to MassMoCA
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

9. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is NZ$483
includes taxes & fees
4 Nov - 5 Nov
New Studio In Town, By the Water
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

10. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is NZ$533
includes taxes & fees
22 Oct - 23 Oct
Downtown | Waterfront | Walk to Shops
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, (10 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$361
includes taxes & fees
19 Oct - 20 Oct
Cozy Home in Pownal VT
"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

12. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (21 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$558
includes taxes & fees
2 Nov - 3 Nov
2-Bdr Apt In Town, By the Water
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

13. 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.
The price is NZ$1,312
includes taxes & fees
13 Oct - 14 Oct
5BR Berkshire Home Mins To The Mountain
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

14. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is NZ$352
includes taxes & fees
26 Oct - 27 Oct
Rose room Victorian home queen bed private bath
A staircase with wooden steps and a white handrail.

15. 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
The price is NZ$983
includes taxes & fees
8 Nov - 9 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A snow-covered outdoor area with a fire pit, tables, and chairs.

16. 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.
The price is NZ$453
includes taxes & fees
13 Oct - 14 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

17. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is NZ$402
includes taxes & fees
12 Oct - 13 Oct
Berkshires Apartment at the Stephentown Hotel
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

18. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is NZ$404
includes taxes & fees
1 Nov - 2 Nov
Lovely 2nd Floor Apartment
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.
The price is NZ$1,062
includes taxes & fees
13 Oct - 14 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A blue house with a porch, a wooden bench, and a door.

20. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is NZ$426
includes taxes & fees
9 Nov - 10 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Nice establishment with great staff. Good heated outdoor pool. Great location. Great activities all seasons. Apartments are well-worn and are not pristine. Not for clean-freaks. Nicer than a college apartment."
Guinevere 1-night trip
Posted 2 hours ago
Jiminy Peak Mountain Resort

Find out more about Florida

Everything you need to know about Florida holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Florida holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Florida holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Florida holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Florida holiday rentals we have selected for you start as low as NZ$179 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Florida rentals

At Expedia, we put the best Florida holiday 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 holiday.

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 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.