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Florida Holiday Rentals

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Holiday Rentals in Florida

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is AU$300
includes taxes & fees
1 Dec - 2 Dec
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AU$251
includes taxes & fees
27 Nov - 28 Nov
Jiminy Peak Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
TV, fireplace, DVD player, books

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

9.6 out of 10, Exceptional, (54)
"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

9.0 out of 10, Wonderful, (42)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AU$349
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Outdoor spa tub

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Interior

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (39)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (211)
"Place was amazing very secluded but close enough to get into town and do things. Our longest drive to go do something was only nine minutes away. Everything was as promised. The only issue we had was the back door entry. The hot tub is right there and when we were standing outside watching nature, we saw bees and wasps going underneath the hot tub. so because we were both chickens, we never went into the hot tub. I probably should’ve called the owner to let him know, but I was a little...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (20)
"The home was beautiful and we enjoyed our stay! The only thing about the location, it’s very remote. We had an event in North Adams and had a nearly impossible time getting a ride share service or taxi to come pick us up. Other than that, a wonderful stay!"
The price is AU$940
includes taxes & fees
2 Dec - 3 Dec
Bear Creek Cabin
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Walk to Mount Snow, Cozy, Clean and Comfortable!
Pool

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (29)
"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...
Walk to Mount Snow, Cozy, Clean and Comfortable!
Berkshire Lake access
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop

Mount Snow's Best View - Sleeps 8-10

10.0 out of 10, Exceptional, (44)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.6 out of 10, Exceptional, (40)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Outdoor spa tub

The Brown House. Indoor pool - Spa - Sauna - Gameroom

8.2 out of 10, Very good, (22)
"It was our yearly Guys weekend, everyone had a Great time. The house with every bedroom having a full bath was fantastic you couldn’t ask for more We spent many hours in the indoor pool and the 2 jacuzzi’s we will definitely stay there again"
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Jacksonville Cabin w/ Wraparound Deck & Views
Interior

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (21)
"Good Condo in a great location"
The price is AU$462
includes taxes & fees
8 Dec - 9 Dec
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (157)
"This was possibly one of the best VRBO experiences for me. Flawless in all respects"
Seasons On Mount Snow - Ski-in/Ski-out
Great Place to get away and have clean fresh air surround you!
Exterior

Great Place to get away and have clean fresh air surround you!

9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
Chic Pittsfield Home With A View!
Property grounds

Chic Pittsfield Home With A View!

8.8 out of 10, Excellent, (8)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
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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Other types of properties in Florida you may be interested in

Blue Vista Motor Lodge
Single Room

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (157)
"Clean. Quiet"
The price is AU$256
includes taxes & fees
1 Dec - 2 Dec
Blue Vista Motor Lodge
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains

Hotel Downstreet

3.0 star property
8.6 out of 10, Excellent, (1044)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is AU$199
includes taxes & fees
10 Dec - 11 Dec
Hotel Downstreet
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is AU$300
includes taxes & fees
1 Dec - 2 Dec
Vacation Village in the 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Florida is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

What can I see and do in Florida?

Savoy Mountain State Forest and Mohawk Trail State Forest are a couple of lovely local spots to get outside and enjoy nature. While here, Green Mountain National Forest and Hoosac Range 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.