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Holiday Rentals in Florida

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Holiday Rentals in Florida

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, 858 reviews
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is €160
includes taxes & fees
9 Jun - 10 Jun
Jiminy Peak Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, 47 reviews
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
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
9.0 out of 10, Wonderful, 25 reviews
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, 117 reviews
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Bear Creek Cabin
10.0 out of 10, Exceptional, 14 reviews
"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"
The price is €567
includes taxes & fees
9 Jun - 10 Jun
Bear Creek Cabin
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, 28 reviews
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
8.8 out of 10, Excellent, 38 reviews
"The home location, layout were awesome. Pics must be older as there was maintenance needed on the basketball/tennis court, pool, and shuffleboard room. Our bachelor party had a good time, once some updates are done, could be a 5 start spot."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, 205 reviews
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, 205 reviews
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 15 reviews
"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...
Private Lake House in the Berkshires
Berkshire Lake access
10.0 out of 10, Exceptional, 41 reviews
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 34 reviews
"We live in three different states and are usually only all together once a year at the oldest sister’s house. This year we decided to go away together after attending a graduation party. Lots of time to talk and laugh! This house was perfect for that!"
Cozy Cottage Along Idyllic Green River
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very good, 19 reviews
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, 39 reviews
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
Mount Snow's Best View - Sleeps 8-10
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, 23 reviews
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, 19 reviews
"Good Condo in a great location"
The price is €316
includes taxes & fees
7 Jun - 8 Jun
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, 28 reviews
"Overall property was good, and the unit was very good. Our needs were minimal, but if we had questions, Tiago was very quick and to respond."
Walk to Mount Snow, Cozy, Clean and Comfortable!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, 35 reviews
"Amazing House, so much character. More than enough room for large family meals and gatherings. My family really enjoyed it. Having no snow was a disappointment, but we will try again another year. Thank you"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 66 reviews
"Probably one of the cleanest places I have ever stayed. The house is perfect. Beautiful views!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
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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.

Other types of properties in Florida you may be interested in

Blue Vista Motor Lodge
2.0 star property
9.8 out of 10, Exceptional, 115 reviews
" Spectacular view of the mountains."
The price is €174
includes taxes & fees
9 Jun - 10 Jun
Blue Vista Motor Lodge
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, 299 reviews
"Beautiful and clean hotel "
The price is €264
includes taxes & fees
25 Jun - 26 Jun
The Williams Inn
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, 585 reviews
"The hotel has been updated with comfortable rooms that are clean and nice. The pool area is clean. Breakfast was great. Easy, fast, and delicious. The staff went above and beyond to be helpful. The only downsides are: rooms surrounding the pool area are loud during open pool hours. Rooms could use a with noice cancelling material in the hallway walls. The parking garage is closed, but not yet under construction. So the surrounding area looks dated and rundown, but the hotel building itself...
The price is €130
includes taxes & fees
9 Jun - 10 Jun
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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.

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, apart-hotels, 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 €160 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?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This holiday home rental outside of Florida is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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. Deerfield River and Campers Beach are a couple of places you'll find in the wider area.

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.

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