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Florida holiday rentals

We found 155 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:20 Nov - 27 Nov

Interior
Outdoor dining
Dining
Property grounds
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

21% off
AU$5,426
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Gourmet kitchen has everything you need to prepare delicious meals
Beautiful period woodwork and Victorian details
Huge wraparound porch is perfect for visiting with family and friends
Build a cozy fire in our wood fireplace, watch the game or play pool!
Exceptional
(154 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
AU$8,321
for 7 nights, 1 home
AU$1,189 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Private kitchen
Terrace/patio
Room
Dining
Exceptional
(20 reviews)

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

Williamstown

12% off
AU$4,094
for 7 nights, 1 cottage
AU$585 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
View of the house and outdoor firepit
Combined living room/kitchen with cathedral ceilings.
Fully-equipped kitchen
Cozy bedroom with double bed and screened-in porch
Exceptional
(66 reviews)

Retreat In The Woods

Savoy

11% off
AU$2,320
for 7 nights, 1 home
AU$331 per night
includes taxes & fees
Retreat In The Woods
Private kitchen
Private kitchen
Interior
Living area
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
AU$3,509
for 7 nights, 1 home
AU$501 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Living area
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
AU$3,542
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
On Site Trails
Interior
Exterior
Interior
Exceptional
(94 reviews)

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

Whitingham

12% off
AU$2,494
for 7 nights, 1 home
AU$356 per night
includes taxes & fees
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
Interior
Living area
Interior
Living area
Very good
(5 reviews)

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

Williamstown

14% off
AU$2,924
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Interior
Interior
Heidi visiting Jane's 18th Century Studio
Interior
Exceptional
(99 reviews)

19th c. Barn in the Berkshires

Cheshire

8% off
AU$3,991
for 7 nights, 1 home
AU$570 per night
includes taxes & fees
19th c. Barn in the Berkshires
Private kitchen
Living area
Room
Bathroom
Very good
(5 reviews)

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

Jacksonville

8% off
AU$4,178
for 7 nights, 1 apartment
AU$597 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 visit Florida

  • Stunning Natural Reserves: Florida boasts captivating nature reserves and national parks, perfect for outdoor enthusiasts.
  • Adventure and Sports Activities: The city is ideal for adventure and outdoor sports, offering a range of exciting experiences.
  • Family-Friendly Atmosphere: Florida provides a charming setting with activities suitable for families, ensuring memorable moments.
  • Cultural Exploration: Visitors can immerse themselves in local culture through various attractions and community events.
  • Comfortable Accommodations: Enjoy a variety of holiday rental options, including private homes and inviting cabins.

Popular types of accommodation in Florida

If you’re seeking a delightful getaway, Florida, Massachusetts, offers a range of comfortable and convenient holiday rental options. The most popular choices include private holiday homes, inviting condos, and charming cabins, perfect for families looking for a memorable stay. Explore the local attractions and immerse yourself in the community's unique charm, ensuring a relaxing and enjoyable experience for all. Discover the beauty of Florida, where your ideal accommodation awaits.

  • Private Holiday Homes: These spacious and comfortable residences are the most sought-after option for visitors in Florida, offering a home-like atmosphere for families and groups.
  • Condos: Ideal for those seeking modern amenities and a convenient location, condos provide a great balance between luxury and affordability.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic charm and a peaceful retreat amidst Florida's beautiful landscapes.
  • Apartments: A practical choice for couples and solo travellers, apartments offer a cosy living space with essential facilities.
  • Cottages: These quaint and charming dwellings are perfect for a tranquil escape, often situated in picturesque settings.**

Top attractions in and around Florida

Florida is an ideal destination for adventure, outdoor, and sports holidays. Within this vibrant city, visitors will discover captivating nature reserves, libraries, and national state parks, offering diverse experiences that cater to outdoor enthusiasts, culture seekers, and families alike. The local attractions provide a blend of natural beauty and cultural interest, ensuring that every traveller finds something memorable to explore during their stay.

  • Natural Bridge State Park: This stunning national park features a remarkable natural limestone bridge and offers scenic vistas, hiking trails, and opportunities for outdoor adventure amidst lush greenery.
  • Mount Greylock State Reservation: A beautiful reserve with the highest peak in Massachusetts, Mount Greylock offers extensive hiking trails, breathtaking views, and rich wildlife, perfect for nature enthusiasts.
  • Reed Brook Preserve: Nestled within Florida, this eco-friendly nature reserve showcases diverse ecosystems, tranquil trails, and a chance to connect with nature while enjoying outdoor activities.

Things to do recommended for couples

Discover the charm of Florida with a leisurely boat ride at sunset and a stroll along scenic coastal paths, perfect for a romantic escape. Enjoy intimate dining and local experiences that capture the essence of the region.

Things to do recommended for families

Families in Florida will delight in local adventures, from sandy beach days to exploring nature trails, offering memorable experiences and enriching family moments.

Things to do recommended for groups

Explore the serene beauty of the Cape Cod National Seashore, enjoy fresh seafood at local eateries, or take a guided tour of historic lighthouses. For a thrilling experience, consider whale watching in the summer months or visiting the vibrant art scene in Provincetown.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Florida

Whether you're journeying with a group, travelling as a family, accompanied by your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Florida with a group: Consider the number of bedrooms required, along with amenities such as a fully equipped kitchen or outdoor space for group gatherings. Fortunately, you can filter for all of these features – and more – on Stayz.
  • Traveling to Florida with young kids: Traveling with young children can be demanding. It is essential to prioritise their comfort and safety, while also ensuring the availability of suitable facilities, such as a private swimming pool. Additionally, it is wise to consider accommodations that are conveniently located near family-friendly attractions.
  • Taking your pets with you to Florida: For some, a family holiday is not complete without their furry companion. If you share this sentiment, consider exploring Stayz properties that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Florida: If you’re seeking holiday lets with special offers for stays of one month or more, you’ve come to the right place. Simply use the appropriate filters to easily discover and save on long-term rentals. You might also want to include options such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Florida

Discover Florida, a charming village ideal for adventure and outdoor sports. Immerse yourself in its family-friendly, romantic atmosphere and explore nearby attractions such as the scenic Florida Keys. Enjoy a mix of great local experiences and budget adventures, perfect for those seeking both tranquillity and a dash of excitement in a delightful American setting.

  • Williamstown: Nestled approximately 16km from Florida, Williamstown is a charming city renowned for its vibrant ski and adventure scenes. Visitors flock to this picturesque destination to enjoy exhilarating outdoor activities, particularly at its well-known ski fields and resorts. The city is also home to a historic college university that adds a unique academic charm to the area. Nature enthusiasts will appreciate the stunning mountainous landscapes and serene lakes that surround Williamstown, providing ample opportunities for hiking and relaxation amidst beautiful scenery.
  • North Adams: Situated in close proximity to Florida, North Adams offers a rich tapestry of adventure, culture, and outdoor experiences. The city's thriving arts scene includes various music concerts and public art installations, making it a cultural hub for visitors. The local art museum and cultural centre are must-see attractions, showcasing the area’s artistic spirit. Outdoor adventurers can also indulge in skiing at the nearby ski fields, ensuring that there's something for everyone, whether you are an art lover or an outdoor enthusiast.
  • Drury: Just 1.6km away from Florida, Drury is a quaint village that beckons adventure seekers and sports enthusiasts alike. Known for its proximity to excellent ski fields and resorts, Drury offers thrilling winter sports experiences. The stunning nearby mountains and natural parks serve as a backdrop for outdoor activities, from skiing to hiking, making it a delightful retreat for nature lovers. This small community provides a peaceful escape while remaining close to the excitement of the surrounding areas.

Booking with Stayz is a breeze

Are you eager to save on your upcoming adventure? Being flexible with your travel dates can lead to great savings, as prices often fluctuate. Additionally, consider booking a longer stay, as this can provide substantial discounts. To discover a Stayz property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a dedicated area for creating new journeys, continuing your current plans, or reviewing and organising your existing bookings. Properties you have saved or secured are now categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Florida holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Florida to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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