Photo by Chris Addams

Florida holiday homes

We found 154 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:25 Dec - 1 Jan

Dining
Terrace/patio
Private kitchen
Living area
Exceptional
(20 reviews)

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

Williamstown

16% off
NZ$5,547
for 7 nights, 1 cottage
NZ$792 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Dining
Living area
Interior
Outdoor dining
Exceptional
(5 reviews)

Charming Home with Lake and Mountain View

Whitingham

8% off
NZ$16,901
for 7 nights, 1 cabin
NZ$2,414 per night
includes taxes & fees
Charming Home with Lake and Mountain View
Property grounds
Outdoor dining
Renovated kitchen
Dining
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$7,384
for 7 nights, 1 home
NZ$1,055 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
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$4,536
for 7 nights, 1 home
NZ$648 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Room
Private kitchen
Private kitchen
Living area
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$5,003
for 7 nights, 1 home
NZ$715 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Exterior detail
Owner and guest parking. Private guest access is located through the porch door.
Hallway view from the bathroom looking toward the kitchen area.
Room
Exceptional
(35 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
NZ$2,115
for 7 nights, 1 apartment
NZ$302 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Interior
Living area
Room
Privacy personified at the Cottage. Enjoy simple country sophistication.
Exceptional
(211 reviews)

Amazing People & Pet-Welcoming Country Haven

Shelburne Falls

9% off
NZ$2,336
for 7 nights, 1 room
NZ$334 per night
includes taxes & fees
Amazing People & Pet-Welcoming Country Haven
Exterior
Interior
Living area
Interior
Exceptional
(97 reviews)

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

Whitingham

19% off
NZ$3,844
for 7 nights, 1 home
NZ$549 per night
includes taxes & fees
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
Living area
Living area
King size bed in 2nd story primary bedroom
Interior
Very good
(5 reviews)

Walk to campus; open concept kitchen/living;nature trail at end of this quiet st

Williamstown

14% off
NZ$3,427
for 7 nights, 1 home
NZ$490 per night
includes taxes & fees
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Bathroom
Living area
Room
Games room
Very good
(5 reviews)

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Jacksonville

8% off
NZ$5,350
for 7 nights, 1 apartment
NZ$764 per night
includes taxes & fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

  • 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)
  • Jiminy Peak Mountain Resort (16.2 mi / 26.1 km)
  • The Hermitage Golf Club (17.2 mi / 27.7 km)
  • The Hermitage Club (18.5 mi / 29.8 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:

  • 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)
  • Brodie Mountain (12 mi / 19.4 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 best area to stay in Florida when booking a holiday rental?
When considering a holiday rental in Florida, Massachusetts, a popular area to stay is near the picturesque downtown. This charming neighbourhood offers a delightful blend of local shops, cafes, and restaurants, creating a vibrant setting for visitors. The area is home to a modest selection of properties, providing a range of options to suit different tastes and budgets.In addition to its quaint appeal, the downtown area is conveniently located near top attractions such as the scenic parks and recreational areas that showcase the natural beauty of the region. Visitors can enjoy leisurely walks or picnics while taking in the stunning landscapes. Just a short drive away, you'll find historical sites that reflect the rich heritage of Florida, making it a great base for those looking to explore both nature and culture.
When is the best time to visit Florida for a holiday rental?
The best time to visit Florida for a holiday rental is during the peak season from March to May, when the weather is delightful and outdoor activities abound. This period attracts a vibrant mix of tourists eager to soak up the sun, enjoy the stunning beaches, and explore lush nature trails. With temperatures typically ranging from 10 to 25 degrees Celsius, March is particularly popular, offering comfortable conditions ideal for sightseeing and enjoying the local attractions.During these months, visitors can indulge in a variety of experiences, from beachside relaxation to hiking in nearby state parks, all while enjoying the convenience of easily accessible amenities. The atmosphere is lively, making it a great time to explore Florida's renowned attractions and outdoor festivals.For those seeking a more budget-friendly option, consider planning your visit in December. While it's the low season, this month offers a unique charm with fewer crowds, allowing for a more peaceful experience while still enjoying the mild winter temperatures.
What are the top attractions in Florida?
In Florida, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. The scenic Mount Tom State Reservation offers hiking trails with stunning views of the Connecticut River Valley, making it a great spot for outdoor enthusiasts. Nearby, the quaint downtown area features local shops and eateries, superb for a leisurely stroll.The historic Florence section is known for its artistic community and the Emily Dickinson Museum, dedicated to the famed poet, gives insight into her life and work. Additionally, the nearby Connecticut River provides opportunities for kayaking and fishing, appealing to those who enjoy water activities.
Are all fees included in the Florida holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Florida holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Florida with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Florida holiday homes?
You can find great discounts on holiday homes in Florida on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Florida holiday home booking on Bookabach?
To find Florida holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Florida?
A long-stay holiday home in Florida is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Florida holiday home?
Book your Florida holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Florida?
Prices for holiday homes in Florida vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Florida to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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