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Holiday homes in Florida

Enjoy your stay and find the best Holiday homes in Florida at affordable prices

Searching for a holiday home in Florida (Massachusetts)? Explore a great selection of vacation homes in Florida to find the one that best fits to your needs, starting from $101 per night. Holiday homes offer a relaxing escape, providing a cozy retreat for vacationers seeking a home away from home.

Holiday-homes in Florida and region (30 miles)
Florida Mountain Log Cabin in Florida, USA

Florida Mountain Log Cabin

Chalet in Florida, Massachusetts , 1 Oleson Road
Featuring mountain views, Florida Mountain Log Cabin features accommodation with a terrace and a balcony, around 19 km from The Clark Art Institute.
  • Parking

Exceptional 4 Reviews 10.0

from $411.62 Show details »

Hoosac Range Retreat in Florida, USA

Hoosac Range Retreat

Holiday home in Florida, Massachusetts , 137 Mohawk Trail
Set in Florida in the Massachusetts region, Hoosac Range Retreat has a balcony.
  • Parking
  • Family rooms

no reviews

from $142.64 Show details »

The Lodge @ America’s Switzerland in North Adams, USA

The Lodge @ America’s Switzerland

Lodge in North Adams near Florida, Massachusetts , 2360 Mohawk Trail
Boasting a garden, a terrace as well as a bar, The Lodge @ America’s Switzerland is situated in North Adams, within 40 km of Bennington Battle Monum...
  • Bar
  • Breakfast in the room

Fabulous 36 Reviews 8.7

from $192.50 Show details »

Charlemont Retreat on Chickley River with EV Charger in Charlemont, USA

Charlemont Retreat on Chickley River wit...

Holiday home in Charlemont near Florida, Massachusetts
Set in Charlemont, within 43 km of The Clark Art Institute, Charlemont Outdoor Retreat on the Chickley River! offers accommodation with free WiFi and ...
  • Parking
  • Pets allowed

no reviews

from $358.67 Show details »

Charming Adams Home Near Dtwn, Trails and More! in Adams, USA

Charming Adams Home Near Dtwn, Trails an...

Holiday home in Adams near Florida, Massachusetts
Charming Adams Home Near Dtwn, Trails and More! is situated in Adams, 37 km from Cranwell Spa & Golf Club, 37 km from Tanglewood Musical Center, and 4...
  • Parking

no reviews

from $101.00 Show details »

Peaceful Family Home with Fire Pit and Large Yard in Williamstown, USA

Peaceful Family Home with Fire Pit and L...

Holiday home in Williamstown near Florida, Massachusetts
Featuring a spa bath, Peaceful Family Home with Fire Pit and Large Yard is set in Williamstown.
  • Parking

no reviews

from $456.67 Show details »

Cozy, Private Cabin on 10 Acres of Woods! in Whitingham, USA

Cozy, Private Cabin on 10 Acres of Woods...

Holiday home in Whitingham near Florida, Massachusetts , 575 Burrington Hill Road
Boasting free bikes, a garden, and a terrace, Cozy, Private Cabin on 10 Acres of Woods! offers accommodation in Whitingham with free WiFi and garden v...
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 1 Reviews 10.0

from $333.00 Show details »

North Getaway Cottage in Williamstown, USA

North Getaway Cottage

Holiday home in Williamstown near Florida, Massachusetts , 111 North Street
North Getaway Cottage is situated in Williamstown, 46 km from Tanglewood, 46 km from Cranwell Spa & Golf Club, as well as 46 km from Tanglewood Musica...
  • Parking

no reviews

from $225.00 Show details »

Cozy Southern Vermont Home with On-Site Trails in Whitingham, USA

Cozy Southern Vermont Home with On-Site...

Holiday home in Whitingham near Florida, Massachusetts
Cozy Southern Vermont Home with On-Site Trails offers accommodation in Whitingham, 19 km from Molly Stark State Park and 30 km from Mount Snow Resort.
  • Parking

Passable 1 Reviews 5.0

from $313.71 Show details »

Rowemont in Jacksonville, USA

Rowemont

Holiday home in Jacksonville near Florida, Massachusetts
Rowemont is situated in Jacksonville.
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • Shower
  • Bath

no reviews

from $159.00 Show details »

Log Cabin Escape in Jacksonville, USA

Log Cabin Escape

Holiday home in Jacksonville near Florida, Massachusetts
Offering mountain views, Log Cabin Escape is an accommodation located in Jacksonville, 46 km from Bennington Museum and 48 km from Southern Vermont Co...
  • Parking
  • Tea/Coffee maker
  • Internet facilities
  • Shower
  • Bath

Good 8 Reviews 7.5

from $223.25 Show details »

Johns Farmhouse in Mount Snow on 120 Acres! in Whitingham, USA

Johns Farmhouse in Mount Snow on 120 Acr...

Holiday home in Whitingham near Florida, Massachusetts
Johns Farmhouse in Mount Snow on 120 Acres! is situated in Whitingham, 43 km from Bennington Battle Monument, 46 km from Stratton Mountain, as well as...
  • Parking
  • Internet facilities
  • Refrigerator
  • Toilet
  • Microwave

Superb 4 Reviews 9.5

from $397.86 Show details »

Two Brooks Lodge in Bennington, USA

Two Brooks Lodge

Holiday home in Bennington near Florida, Massachusetts , 1054 Sawmill Road
Featuring river views, Two Brooks Lodge offers accommodation with a garden, a bar and barbecue facilities, around 6.8 km from Bennington Museum.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms
  • Tea/Coffee maker

Good 8 Reviews 7.5

from $222.24 Show details »

Jacksonville Cabin with Wraparound Deck and Views in Jacksonville, USA

Jacksonville Cabin with Wraparound Deck...

Holiday home in Jacksonville near Florida, Massachusetts
Situated 46 km from Bennington Battle Monument, 49 km from Stratton Mountain and 44 km from Bennington Museum, Jacksonville Cabin with Wraparound Deck...
  • Parking
  • Internet facilities
  • Shower
  • Bath
  • TV

Exceptional 2 Reviews 10.0

from $265.00 Show details »

Cozy Treetop Hideaway Near Harriman Reservoir! in Wilmington, USA

Cozy Treetop Hideaway Near Harriman Rese...

Holiday home in Wilmington near Florida, Massachusetts
Located in Wilmington, 34 km from Bennington Battle Monument and 43 km from Stratton Mountain, Cozy Treetop Hideaway Near Harriman Reservoir! provides...
  • Parking
  • Pets allowed

Good 2 Reviews 7.0

from $291.67 Show details »

Wilmington Escape in Wilmington, USA

Wilmington Escape

Holiday home in Wilmington near Florida, Massachusetts
Situated in Wilmington, 41 km from Bennington Battle Monument, Wilmington Escape features accommodation with a garden, free WiFi and an ATM.
  • Parking
  • Pets allowed
  • Tea/Coffee maker
  • Shower
  • Bath

Very good 3 Reviews 8.0

from $323.00 Show details »

Picturesque Cottage with Sunroom on Ashmere Lake! in Hinsdale, USA

Picturesque Cottage with Sunroom on Ashm...

Holiday home in Hinsdale near Florida, Massachusetts
Located 32 km from Cranwell Spa & Golf Club, 32 km from Tanglewood Musical Center and 40 km from Norman Rockwell Museum, Picturesque Cottage with Sunr...
  • Parking

Exceptional 1 Reviews 10.0

from $208.00 Show details »

Farmhouse on the Road in Wilmington, USA

Farmhouse on the Road

Holiday home in Wilmington near Florida, Massachusetts
Situated in Wilmington, 35 km from Bennington Battle Monument, 42 km from Stratton Mountain and 33 km from Bennington Museum, Farmhouse on the Road fe...
  • Parking

Okay 3 Reviews 6.0

from $303.86 Show details »

Wilmington Getaway with Pool Access Near Hiking! in Wilmington, USA

Wilmington Getaway with Pool Access Near...

Holiday home in Wilmington near Florida, Massachusetts
Featuring a sauna, Wilmington Home with Pool Access, 20 Mins to Mt Snow is located in Wilmington.
  • Parking
  • Sauna
  • Fitness centre
  • Internet facilities
  • Iron

Disappointing 1 Reviews 4.0

from $296.67 Show details »

Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! in Hancock, USA

Hancock Log Cabin Retreat 2 Miles to Jim...

Holiday home in Hancock near Florida, Massachusetts
Situated in Hancock, 34 km from Tanglewood and 34 km from Cranwell Spa & Golf Club, Hancock Log Cabin Retreat 2 Miles to Jiminy Peak! provides accommo...
  • Parking
  • Shower
  • Bath
  • TV
  • Hairdryer

Exceptional 1 Reviews 10.0

from $226.00 Show details »

Private Wooded Cabin, 8 Mi to Sundance Ski and Town! in Wilmington, USA

Private Wooded Cabin, 8 Mi to Sundance S...

Holiday home in Wilmington near Florida, Massachusetts
Set 36 km from Bennington Battle Monument, 43 km from Stratton Mountain and 34 km from Bennington Museum, Private Wooded Cabin, 8 Mi to Sundance Ski a...
  • Parking
  • Pets allowed
  • Internet facilities
  • Shower
  • Bath

no reviews

from $317.00 Show details »

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak in Hancock, USA

Mountain View Suite Sleeps 4 Ski OnOff J...

Holiday home in Hancock near Florida, Massachusetts , Corey Road 37
Situated about 33 km from Tanglewood, Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Exceptional 6 Reviews 10.0

from $171.33 Show details »

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 in Hancock, USA

Unique Yeti-Theme Ski On Off Suite Jimin...

Holiday home in Hancock near Florida, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 features free WiFi and a fitness ...
  • Parking
  • Fitness centre
  • Indoor pool
  • Outdoor pool
  • Swimming pool

Superb 16 Reviews 9.2

from $162.77 Show details »

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak in Hancock, USA

Ski On Off 1BR Suite 1st Flr Sleeps 4 Ji...

Holiday home in Hancock near Florida, Massachusetts , 37 Corey Road
Located about 33 km from Tanglewood, Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak offers accommodation with an outdoor pool and free WiFi.
  • Parking
  • Fitness centre
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 4 Reviews 8.8

from $156.75 Show details »

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn in Hancock, USA

Deluxe Ski On Off 1BR Suite Sleeps 4 on...

Holiday home in Hancock near Florida, Massachusetts , 37 Corey Road
Within 33 km of Tanglewood and 33 km of Cranwell Spa & Golf Club, Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn features free WiFi and a fitness ...
  • Parking
  • Fitness centre

Superb 12 Reviews 9.0

from $183.08 Show details »

Number of Holiday homes in Florida 75
Number of guest ratings 4
Average price per night $317.24
Lowest price per night $101.00
Highest price per night $701.33

Most popular Holiday-homes in Florida

The most popular Holiday-homes in Florida based on average guest rating (Top 10).

Cheapest Holiday-homes in Florida

The cheapest Holiday-homes in Florida based on room rate per night (Top 10).

Most booked Holiday-homes in Florida

The most booked Holiday-homes in Florida based on popularity with guests (Top 10).

Holiday homes in Florida (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Florida can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Florida for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Florida should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com