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Florida Holiday Rentals

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Holiday Rentals in Florida

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (858)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is NZ$276
per night
17 Jun - 18 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)
"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)
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
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)
"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)
"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 NZ$972
per night
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)
"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)
"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)
"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)
"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)
"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)
"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)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very good, (19)
"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)
"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)
"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)
"Good Condo in a great location"
The price is NZ$542
per night
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)
"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)
"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)
"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)
"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)
" Spectacular view of the mountains."
The price is NZ$305
per night
9 Jun - 10 Jun
Blue Vista Motor Lodge
The Williams Inn
4.0 star property
9.6 out of 10, Exceptional, (299)
"Beautiful and clean hotel "
The price is NZ$464
per night
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)
"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 NZ$229
per night
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.

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?

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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