Florida, MA Resort Rentals

Florida Resorts

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Price Dropped

Apartment

Getaway Near Mass MoCA, Great Hiking, Scenic Views

10.0

Exceptional

(32 Reviews)

1 Bedroom 2 Baths 2 Guests 450 ft²

US $136/Night 7 Nights - US $949

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Ski Chalet

Florida Mountain Log Cabin

10.0

Exceptional

(4 Reviews)

3 Bedrooms 1 Bath 6 Guests 904.17 ft²

US $284/Night 7 Nights - US $1,988

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Price Dropped

Bed & Breakfast

UU Rowe Camp and Conference Center

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath

US $207/Night 7 Nights - US $1,448

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House

The Greylock Cabin

10.0

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 4 Guests 880 ft²

US $374/Night 7 Nights - US $2,615

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Apartment

North Adams Apartment with Renovated Kitchen

9.0

Exceptional

(2 Reviews)

2 Bedrooms 1 Bath 4 Guests 796.53 ft²

US $422/Night 7 Nights - US $2,954

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Cabin

Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 4 Guests

US $229/Night 7 Nights - US $1,603

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Apartment

The Allen House

8.5

Fabulous

(2 Reviews)

3 Bedrooms 1 Bath 5 Guests 129.17 ft²

US $368/Night 7 Nights - US $2,578

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Cottage

Brookside cottage near the mountains and outdoor recreation

10.0

Exceptional

(1 Review)

2 Bedrooms 1 Bath 4 Guests

US $202/Night 7 Nights - US $1,414

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Charlemont Chalet - A 15 Acre Private Retreat

House

Charlemont Chalet - A 15 Acre Private Retreat

1 Bedroom 3 Baths 6 Guests 2497.23 ft²

US $332/Night 7 Nights - US $2,322

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Highly Rated

House

Retreat In The Woods

9.8

Exceptional

(66 Reviews)

2 Bedrooms 1 Bath 4 Guests

US $210/Night 7 Nights - US $1,471

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Ski Chalet

The Mountain Cottage

2 Bedrooms 1 Bath 5 Guests 904.17 ft²

US $284/Night 7 Nights - US $1,988

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Apartment

A First floor 2-bedroom apartment in North Adams. Plenty of off-street parking.

9.8

Exceptional

(7 Reviews)

2 Bedrooms 1 Bath 4 Guests

US $169/Night 7 Nights - US $1,186

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More Top-Rated Resorts in Florida Area

Why Choose Rent By Owner for your Florida Resorts?

What makes our Resorts special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Florida

When should you plan your Resorts stay?

Choosing the optimal time to vacation here can significantly enhance your experience, as the region offers different seasonal highlights that suit various preferences and travel goals.

Peak Season Highlights

Winter (December to February)

During the winter months, the area sees a surge of visitors seeking warmer weather and outdoor activities, making it an ideal time for a relaxing getaway.

Average Temperature Daytime: Average daytime temperatures range from 70°F to 80°F - Nighttime: Nights are cooler, with temperatures dropping to around 50°F to 60°F

Summer (June to August)

The summer period attracts travelers looking to enjoy the region’s beaches and vibrant events, ensuring lively resorts during this peak season.

Average Temperature Daytime: Temperatures typically hover between 85°F and 90°F - Nighttime: Evenings tend to be warm, with lows around 70°F to 75°F

Off-Season Highlights

Spring (March to May)

In spring, the area offers more peaceful accommodations with pleasant weather, perfect for exploring at a relaxed pace.

Average Temperature Daytime: Daytime temperatures generally range from 65°F to 75°F - Nighttime: Nights cool down to about 45°F to 55°F

Fall (September to November)

Autumn brings fewer crowds and mild weather, making it an excellent time to enjoy the serene beauty of the destination’s resorts.

Average Temperature Daytime: Average temperatures are between 70°F and 80°F - Nighttime: Nighttime temperatures often fall to around 50°F to 60°F

Weekly Weather Forecast for Florida

How to Book Your Florida Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Florida

More Top-Rated Resorts in Florida Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy a private outdoor pool overlooking scenic views in your vacation rental.
Relax on spacious sun decks or patios perfect for soaking up the sunshine.
Take advantage of well-maintained grilling areas for outdoor dining experiences.
Explore lush gardens or landscaped yards surrounding your resort stay.
Make use of outdoor sports facilities such as tennis courts or basketball courts.
Benefit from easy access to nearby beaches or waterfronts for outdoor activities.
Unwind in hammock areas or shaded lounging spaces within the property's outdoor settings.

Top Attractions Around Florida

What attractions are nearby?

In this area, you can enjoy a variety of outdoor activities, cultural experiences, and scenic excursions that highlight the best of Florida and Massachusetts, making your stay at the resorts here both relaxing and adventure-filled.

Family Activities

LEGOLAND Florida Resort: Experience a world of imagination and creativity at this family-friendly attraction, perfect for children of all ages.
Gulf Coast Beaches: Relax and play along the pristine sandy shores, offering endless opportunities for swimming, building sandcastles, and picnicking with loved ones.
Wildlife Walks at Myakka River State Park: Discover Florida’s diverse ecosystems on guided or self-led nature walks ideal for exploring as a family.
Florida’s Natural History Museum: Engage your family in interactive exhibits that bring the area's history and natural environment to life.

Plimoth Patuxet Museums: Step back in time and learn about early American history through immersive exhibits and living history programs suitable for all ages.
Boston Children's Museum: Ignite your children's curiosity with hands-on exhibits and activities designed to entertain and educate visitors of every age.
Freedom Trail: Embark on an outdoor historical journey that takes you through the famous sites of Massachusetts’ rich past.
Walden Pond: Enjoy a peaceful day by the water, where you can relax, swim, or explore the literary history of Henry David Thoreau in the surrounding area.

Adult Activities

Fishing Charters: You can enjoy a day of fishing on the region's abundant waters, experiencing the thrill of catching local species and soaking in the scenic views.
Gulf Coast Beaches: Spend your time relaxing or engaging in water sports along the picturesque coastlines that define this destination’s reputation for pristine beaches.
Wildlife Tours: Explore the area's diverse ecosystems through guided wildlife tours, where you may see native birds, marine life, and other local fauna.
Water Sports Activities: Participate in exciting activities such as paddleboarding, jet skiing, or snorkeling, perfect for adventure seekers looking to make the most of your stay.

Other Places to Stay in Florida, MA

Drury

Explore 61 Properties

More Places to Stay Near Florida

Florida Travel Tips

How Can You Make the Most of Your Stay?

Plan your visit during off-peak seasons: Visiting outside of peak times can help you enjoy a more relaxing stay and better rates on your accommodations.
Explore local dining options: Savor authentic regional cuisine by discovering nearby restaurants, adding a flavorful dimension to your stay here.
Take advantage of outdoor activities: Engage in the area's natural beauty through outdoor pursuits like beaches, parks, or trails, ensuring an active and memorable vacation.
Book your lodging early: Secure your preferred resort accommodations well in advance to guarantee availability and better deals for your trip to this destination.

Transportation Options

Rental Cars: Renting a car offers the freedom to explore the area at your own pace, especially when staying in a Florida resort.
Public Transit: Buses and trains provide affordable and convenient transportation within the region, connecting you directly to local attractions and amenities.
Taxis and Rideshare Services: Taxis, Uber, and Lyft can quickly get you to your destination, ideal for short trips around the area.
Shuttle Services: Many resorts offer shuttle options to nearby points of interest, making travel hassle-free during your stay in this destination.

Local Customs Options

Sunshine State Etiquette: In Florida, it is customary to greet neighbors with a friendly wave and maintain a relaxed, casual demeanor, reflecting the area's warm and welcoming atmosphere.
Beach Respect and Treading Lightly: When visiting coastal regions like this destination, local customs emphasize respecting private properties and avoiding leaving trash on the beaches to keep the shoreline pristine.
Florida's Fishing Traditions: Angling is a popular activity in the area, and it's customary to follow local regulations and practice catch-and-release to preserve the region's abundant aquatic life.
Casual Dining Culture: The region encourages a laid-back dining experience where enjoying fresh seafood and engaging in friendly conversations are part of the local customs.

Historical Reverence: Here in Massachusetts, honoring the area's rich colonial history by observing local memorials and participating in historical tours is a common tradition.
Seafood Appreciation: The local customs around here include savoring fresh New England seafood, especially during seasonal festivals that celebrate regional cuisine.
Community Celebrations: Participating in neighborhood events like local parades and fairs reflects the close-knit spirit typical of this historic region.
Respect for Nature: Visitors are encouraged to respect the natural landscapes by following conservation guidelines when exploring parks and coastal areas.

Florida Resorts Frequently Asked Questions

1. What are the top Resorts in Florida?

There are a lot of options in Florida. If you plan on staying in the Florida area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Florida:

2. How many Resorts are available in Florida?

Currently, the total number of properties listed by RBO in 2026 is over 89 in the Florida area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Florida. 

3. What is the cancellation policy for resorts in this area?

Cancellation policies vary depending on the specific resort listing. It’s recommended to review the individual policy details outlined in the reservation terms or contact the property owner directly for clarification.

4. Are there any additional fees I should be aware of when booking a resort?

Additional fees such as cleaning, resort charges, or security deposits are typically specified in the listing details. For precise information, please refer to the property description or reach out to the owner before confirming your booking.

5. What amenities can I expect at the resorts in this region?

Amenities offered can include pools, fitness centers, on-site dining, and more. To ensure the resort meets your needs, review the amenities listed in the property profile or contact the host for specific inquiries.

6. How do I modify or cancel my reservation if my plans change?

Reservation modification and cancellation procedures depend on the property's policies. You can initiate changes through the booking platform or contact the property owner directly for assistance.

7. Is there a minimum stay requirement for resorts in this destination?

Minimum stay requirements vary between properties. Please check the booking details for each resort or contact the owner to confirm the minimum number of nights needed for your reservation.