Winter Rentals in Florida:【 GREAT PRICES 】 Rent By Owner

Florida Winter Rental

House

Casa Cuarzo, Relax in the mountains

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 5 Guests 1615 ft²

CA $493/Night 7 Nights - CA $3,449

View Deal

House

Haras El Despertar

10.0

Exceptional

(3 Reviews)

6 Bedrooms 6 Baths 20 Guests 391.81 ft²

CA $154/Night 7 Nights - CA $1,079

View Deal

House

House/Chalet Residential Zone

3 Bedrooms 1 Bath 8 Guests 1184 ft²

CA $231/Night 7 Nights - CA $1,615

View Deal

House

Casa Cuarzo, Relax en la sierra

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 5 Guests 1614.59 ft²

CA $267/Night 7 Nights - CA $1,868

View Deal

Cabin

Cabaña en Haras El Despertar

1 Bedroom 1 Bath 3 Guests

CA $196/Night 7 Nights - CA $1,370

View Deal

House

La Escondida- Escapada Romántica

9.9

Exceptional

(79 Reviews)

1 Bedroom 1 Bath 2 Guests 484.38 ft²

CA $164/Night 7 Nights - CA $1,150

View Deal

Ski Chalet

Vergel de San Francisco - sierras, nature and relax

2 Bedrooms 1 Bath 4 Guests

CA $94/Night 7 Nights - CA $661

View Deal

Ski Chalet

Cabaña Panambi

9.8

Exceptional

(48 Reviews)

2 Bedrooms 1 Bath 4 Guests 861.11 ft²

CA $179/Night 7 Nights - CA $1,255

View Deal

Other

Gorgeous 7-bedroom farmhouse with AC in charming Soca

7 Bedrooms 6 Baths 22 Guests 6000 ft²

CA $1,470/Night 7 Nights - CA $10,289

View Deal

Ski Chalet

Cabaña El Trisquel

9.7

Exceptional

(45 Reviews)

1 Bedroom 1 Bath 3 Guests 538.2 ft²

CA $151/Night 7 Nights - CA $1,054

View Deal

House

Estancia Aguila Blanca

9.7

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 3 Guests 269.1 ft²

CA $297/Night 7 Nights - CA $2,076

View Deal

Casa de campo - retiro con encanto en las sierras

Highly Rated

Ski Chalet

Casa de campo - retiro con encanto en las sierras

9.6

Exceptional

(63 Reviews)

2 Bedrooms 1 Bath 3 Guests 807.29 ft²

CA $130/Night 7 Nights - CA $910

View Deal

More Top-Rated Winter Rental in Florida Area

Why Choose Rent By Owner for your Florida Winter Rental?

What makes our Winter Rental 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 Winter Rental stay?

To make the most of your winter escape, consider visiting during the region's mildest months when the weather comfortably supports outdoor activities and local events, ensuring you enjoy your stay in this destination at its best.

Peak Season Highlights

Winter (December to February)

During the winter months, this destination experiences its peak season with warm temperatures, making it ideal for enjoying outdoor activities and relaxing by the coast.

Average Temperature Daytime: 25°C to 30°C - Nighttime: 18°C to 22°C

Spring (March to May)

Spring marks another busy period when the weather is comfortably warm, attracting visitors seeking pleasant conditions and vibrant local events.

Average Temperature Daytime: 22°C to 28°C - Nighttime: 14°C to 19°C

Off-Season Highlights

Late Summer (June to August)

The late summer months tend to be quieter, offering a more relaxed atmosphere with slightly cooler temperatures suitable for exploring the area without large crowds.

Average Temperature Daytime: 20°C to 24°C - Nighttime: 12°C to 16°C

Fall (September to November)

Fall sees fewer visitors, providing a peaceful escape with mild weather and lower prices for your winter rentals in this region.

Average Temperature Daytime: 21°C to 26°C - Nighttime: 13°C to 18°C

Weekly Weather Forecast for Florida

How to Book Your Florida Winter Rental

What's our booking process?

Our platform allows you to browse a curated selection of winter rental. 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 Winter Rental in Florida Area

Common Winter Rental Amenities

What amenities can you expect?

Our Winter Rental 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 swimming pool to relax and soak up the sun.
Benefit from spacious patios or decks ideal for outdoor dining and entertaining.
Take advantage of lush gardens or landscaped yards that enhance your outdoor experience.
Make the most of outdoor grilling areas or BBQ facilities for delicious meals al fresco.
Relax in shaded pergolas or covered sitting areas perfect for enjoying the fresh air.
Utilize well-maintained sports courts such as tennis or volleyball for active recreation.
Discover nearby outdoor activities like walking trails or beachfront access, depending on the property location.

Top Attractions Around Florida

What attractions are nearby?

Explore a variety of outdoor activities and cultural attractions nearby when you choose your winter rentals in Florida, Uruguay, where the region offers an inviting mix of scenic parks, vibrant local markets, and charming coastal spots to enjoy throughout your stay.

Family Activities

Beach Day at Playa Mansa: Spend a relaxing day swimming and building sandcastles on the calm shores of this popular beach in the region.
Visit to Museo del Carnaval: Explore vibrant displays celebrating local culture and festivities, offering educational fun for the entire family.
Adventure Park Activities: Enjoy outdoor fun with zip lines, obstacle courses, and playgrounds designed for children and adults alike in the area.
Boat Tours around the Coast: Experience scenic boat rides along the coast, providing breathtaking views and memorable family moments here.

Adult Activities

Exploring local beaches: Relax and unwind along the pristine sands and clear waters that define this coastal area, perfect for sunbathing or enjoying a peaceful walk.
Sampling regional cuisine: Indulge in authentic dishes at nearby restaurants, offering a taste of the area's unique seafood and culinary traditions.
Participating in water sports: Experience thrilling activities like kayaking, paddleboarding, or windsurfing to make the most of the region’s inviting waterways.
Visiting cultural sites: Discover local history and art by exploring museums, galleries, or historic landmarks situated within easy reach of your winter rentals.

Other Places to Stay in Florida

Robaina Park

Explore 936 Properties

Florida

Explore 933 Properties

San Cono Chapel

Explore 929 Properties

Reboledo

Explore 505 Properties

Cerra Colorado

Explore 154 Properties

Jose Batlle y Ordonez

Explore 98 Properties

Venticinco de Agosto

Explore 35 Properties

More Places to Stay Near Florida

Florida Travel Tips

How Can You Make the Most of Your Stay?

Explore Local Cuisine: Take time to indulge in authentic dishes at local eateries to fully experience the region's culinary traditions.
Enjoy Outdoor Activities: Make the most of the area's natural beauty by participating in outdoor pursuits such as walking along scenic beaches or exploring nearby parks.
Visit Cultural Sites: Immerse yourself in the local history and culture by visiting museums, galleries, or historical landmarks unique to this destination.
Plan Ahead for Popular Attractions: Secure reservations or tickets early for well-known spots to avoid disappointment and maximize your enjoyment during peak times.

Transportation Options

Car Rental Services: Renting a car offers you the flexibility to explore this destination at your own pace, with many local providers offering a wide selection of vehicles suitable for any travel plans.
Public Buses: The regional bus system provides an affordable and reliable way to navigate the area, connecting key parts of the region comfortably and efficiently.
Taxis and Rideshare: Taxis and rideshare services are available throughout here, providing convenient transportation options for quick and direct trips around the region.
Bicycle Rentals: For those seeking a more active experience, bicycle rentals are popular here, allowing you to enjoy scenic routes while exploring the area's natural beauty.

Local Customs Options

Traditional Asado Participating in an asado, a social barbecue, is a cherished custom where locals gather to share grilled meats and enjoy lively conversations.
Mate Sharing It’s common to see residents exchanging mate, a traditional herbal tea, in social settings, symbolizing friendship and hospitality.
Celebrating Carnival The vibrant Carnival festivities feature colorful costumes and lively parades that reflect the region’s rich cultural heritage.
Respect for Punctuality Being punctual is valued during social gatherings and events, highlighting the importance of respecting others time here.

Frequently Asked Questions About Florida Winter Rentals

1. What are the top Winter Rentals 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 Winter Rentals in Florida:

2. How many Winter Rentals are available in Florida?

Currently, the total number of properties listed by RBO in 2026 is over 44 in the Florida area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Florida. 

3. What is the cancellation policy for winter rentals in Florida, Uruguay?

The cancellation policy varies by property, so it is best to review the specific listing details or contact the owner directly for exact terms.

4. Are there any additional fees associated with booking a winter rental in this area?

Additional fees such as cleaning fees, service charges, or security deposits may apply. Please check the listing details or reach out to the owner for a complete fee breakdown.

5. How do I confirm my booking and what information do I need to provide?

You can confirm your reservation through the booking platform by providing necessary details such as identification and payment information, but verify the process and requirements listed on the property page or with the owner.

6. Is there a minimum stay requirement for winter rentals during the season?

Minimum stay requirements can differ depending on the property, so consult the listing description or contact the host directly to confirm the length of stay needed.

7. What amenities are typically included in winter rentals in this region?

Amenities vary per property but often include essentials like Wi-Fi, heating, and kitchen facilities. For specific amenities, please refer to the individual listing or contact the owner for further details.