Photo by Chris Addams

Florida holiday homes

We found 156 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Florida that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Florida

Showing deals for:13 Nov - 20 Nov

Renovated kitchen
Outdoor dining
Dining
Property grounds
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$7,495
for 7 nights, 1 home
NZ$1,071 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Room
Terrace/patio
Living area
Dining
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,643
for 7 nights, 1 cottage
NZ$806 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Wood stove in living room
Combined living room/kitchen with cathedral ceilings.
View of the house and outdoor firepit
Fully-equipped kitchen
Exceptional
(66 reviews)

Retreat In The Woods

Savoy

11% off
NZ$2,736
for 7 nights, 1 home
NZ$391 per night
includes taxes & fees
Retreat In The Woods
Privacy personified at the Cottage.  Enjoy simple country sophistication.
Living area
The cottage garden in full summer bloom
Interior
Exceptional
(211 reviews)

Amazing People & Pet-Welcoming Country Haven

Shelburne Falls

9% off
NZ$2,244
for 7 nights, 1 room
NZ$321 per night
includes taxes & fees
Amazing People & Pet-Welcoming Country Haven
Living area
Private kitchen
Private kitchen
Interior
Exceptional
(18 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$4,164
for 7 nights, 1 home
NZ$595 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Exterior
Outdoor dining
Property grounds
Living area
Exceptional
(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off
NZ$4,357
for 7 nights, 1 home
NZ$622 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Interior
Interior
On Site Trails
Living area
Exceptional
(93 reviews)

The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome

Whitingham

11% off
NZ$2,556
for 7 nights, 1 home
NZ$365 per night
includes taxes & fees
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
Heidi visiting Jane's 18th Century Studio
Interior
Interior
Interior
Exceptional
(99 reviews)

19th c. Barn in the Berkshires

Cheshire

8% off
NZ$4,917
for 7 nights, 1 home
NZ$702 per night
includes taxes & fees
19th c. Barn in the Berkshires
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting friendly Florida

The forests, mountains and gardens display a scene truly unique to Florida. Well known for its camping, hiking and parks, this welcoming city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Florida

Are you looking for things to do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Florida a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Berkshire East Ski Resort (7.8 mi / 12.5 km)
  • Waubeeka Golf Links (11.6 mi / 18.7 km)
  • Prospect Mountain Cross-Country Ski Center (14.7 mi / 23.7 km)
  • Prospect Mountain Nordic Ski Center (15.2 mi / 24.4 km)
  • Jiminy Peak Mountain Resort (16.2 mi / 26.1 km)
  • The Hermitage Golf Club (17.2 mi / 27.7 km)

Exploring the natural features in Florida

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Florida is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Tannery Falls (3.1 mi / 5 km)
  • Windsor Lake Park (4.5 mi / 7.2 km)
  • Mount Greylock (8.2 mi / 13.1 km)
  • Mount Greylock State Reservation (8.9 mi / 14.2 km)
  • Harriman Reservoir (12.6 mi / 20.2 km)
  • Mount Greylock State Reservation Visitor Center (12.9 mi / 20.8 km)

Transport options to and around Florida

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 22 mi (35.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Albany, NY (ALB-Albany Intl.), which is 40.9 mi (65.8 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Florida?
The most desirable types of holiday homes in Florida are cottages. Searching for something different? Bookabach has a variety of options to match our guests' unique needs, so you'll see holiday homes in all sizes and shapes. The perfect home away from home is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Florida?
A range of factors can affect what you'll pay for a holiday home in Florida, like the season, length of stay and type of property. However, all our holiday homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Florida?
Prices for beach houses in Florida can differ depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Bookabach and the number of guests to view your options and prices. From there you can use the filters to refine your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Florida?
You're in luck! There are. You'll have a choice of two holiday homes that allow pets in Florida. Many of our pet-friendly holiday homes come with an outdoor space for your fur baby to have fun in, dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Bookabach.
What are popular home amenities in Florida?
A firepit, a nearby river and a barbecue grill are rated the most popular home amenities in Florida. Whether you plan to go on your own, with a partner or a group of family members, Bookabach will help you find a holiday home that fits your tastes with all the features you need.
Are there holiday homes in Florida that welcome kids?
Florida has two family-friendly holiday homes. And finding a stay that welcomes little ones is a cinch with our "Properties good for families" filter. As well as having the whole place to yourselves, you can also look forward to conveniences and perks like living rooms, kitchens and pools.
What are the top attractions for families in Florida?
Keep the kids busy at these fun family-friendly attractions in Florida:
  • Massachusetts Museum of Contemporary Art
  • Natural Bridge State Park
  • Western Gateway Heritage State Park
Can I find two-bedroom holiday homes in Florida?
Florida has two two-bedroom holiday properties that you can choose from. Experience a holiday home with all the space and comfort you're looking for at a price that won't break the bank on Bookabach.
Are there holiday homes with WiFi in Florida?
Florida has two holiday homes with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to catching up on social media, these Bookabach homes make it a breeze to go online.
How old do you have to be to rent a holiday home in Florida?
The minimum age permitted can vary across properties on Bookabach, so be sure to look at the rules of the holiday home in Florida you're considering. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Florida for?
It all depends on the Florida property. To see a list of options offering extended stays, just enter your dates and guest number into Bookabach. Enjoy having the place to yourself, along with amenities such as a full kitchen, air conditioning and an outdoor space where the kids can play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

More holiday ideas