1. USA
  2. Florida
  3. Winter Rental

Discover Your Perfect Florida Winter Rental

Florida Winter Rental

|
10.0 (20 Reviews)
Apartment
Little Italy - Welcome to Rome
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
More Top-Rated Winter Rental in Florida Area

Why Choose Rent By Owner for your Florida Winter Rental?

What makes our Winter Rental special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
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 stay during the cooler months, consider planning your visit to this destination when the weather is mild and crowds are fewer, ensuring a comfortable and enjoyable experience with your chosen winter rentals here.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy warm weather and sunny skies, making it ideal for outdoor activities and relaxing in your winter rentals.

Average Temperature Daytime: high 70s to low 80s°F - Nighttime: mid 60s to low 70s°F
spring
Spring Break (March to April)

This is a lively time with pleasant temperatures and numerous events, perfect for exploring and enjoying your stay in the area.

Average Temperature Daytime: mid 70s to high 80s°F - Nighttime: mid 60s to mid 70s°F

Off-Season Highlights

image
Summer (June to August)

While the summer can be hot and humid, it’s a quieter period to secure affordable winter rentals before the peak season begins.

Average Temperature Daytime: high 80s to low 90s°F - Nighttime: mid 70s to mid 80s°F
image
Fall (September to November)

The region experiences milder weather and fewer tourists, offering a peaceful atmosphere for your winter rentals.

Average Temperature Daytime: high 70s to low 80s°F - Nighttime: mid 60s to mid 70s°F

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

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

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 relaxing by the private outdoor pool, perfect for unwinding after a day of exploring the region.
  • Take advantage of a spacious patio area equipped for outdoor dining and entertaining with family and friends.
  • Make the most of a lush landscaped backyard that offers a tranquil setting within the area’s warm climate.
  • Utilize outdoor grilling facilities to prepare delicious meals under the sun or stars.
  • Relax on comfortable lounge chairs around your rental’s poolside, soaking up the Florida sunshine.
  • Benefit from well-maintained outdoor spaces designed for recreational activities such as cornhole or bocce ball.
  • Enjoy direct access to nearby outdoor recreation, including walking trails or beach access, depending on the property location.

Top Attractions Around Florida

What attractions are nearby?

During your stay here, you'll find a variety of outdoor activities, cultural attractions, and recreational opportunities just moments from your Florida winter rental, allowing you to fully enjoy the vibrant local scene and make the most of your time in this destination.

image
image

Family Activities

  • Visit Walt Disney World Resort: Experience the magic and thrill of world-famous theme parks, perfect for creating unforgettable family memories here in Florida.
  • Explore Everglades National Park: Discover unique wildlife and ecosystems through guided tours and airboat rides that make the region a fascinating adventure for all ages.
  • Relax on Clearwater Beach: Enjoy the soft white sands and calm waters ideal for family-friendly activities such as swimming, building sandcastles, or simply soaking up the sun.
  • Discover Kennedy Space Center Visitor Complex: Inspire young explorers with engaging exhibits and interactive experiences centered around space exploration in this iconic Florida destination.
image

Adult Activities

  • Deep-Sea Fishing: Experience the thrill of deep-sea fishing off the coast here, where you can enjoy a day filled with adventure and the chance to catch some incredible marine life.
  • Golfing Adventures: Play a round on world-renowned golf courses designed to challenge enthusiasts and provide stunning views of the surrounding area.
  • Water Sports: Engage in water sports such as paddleboarding, jet skiing, or kayaking to make the most of the warm weather and pristine waters here.
  • Sunset Cruises: Take a relaxing cruise during sunset for breathtaking views and a peaceful way to wind down after a day exploring the region.

Other Places to Stay in Florida, FL

Florida Gulf Coast
Explore 65,937 Properties
North West Florida
Explore 61,817 Properties
Orlando
Explore 43,360 Properties
Fort Walton Beach - Destin
Explore 29,826 Properties
Osceola County
Explore 27,959 Properties
Kissimmee
Explore 27,862 Properties
Panama City
Explore 24,155 Properties
Panama City Beach
Explore 21,042 Properties
Walton County
Explore 20,058 Properties
Disney's Maingate West
Explore 19,880 Properties
Bay County
Explore 19,122 Properties
Four Corners
Explore 18,995 Properties
More Places to Stay Near Florida

Florida Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Beaches: Take advantage of the stunning coastlines by visiting nearby beaches, ensuring your stay is filled with relaxing days on the sand and in the surf.
  • Discover Regional Cuisine: Savor the area's diverse culinary offerings by trying local seafood and regional specialties at recommended eateries during your visit.
  • Plan Outdoor Activities: Make the most of the pleasant climate by engaging in outdoor pursuits such as boating, fishing, or scenic nature walks around your rental location.
  • Visit Cultural Attractions: Enhance your trip by exploring key cultural sites and events that showcase the unique heritage and vibrant arts scene here.

Transportation Options

  • Car Rentals: Renting a vehicle gives you the flexibility to explore various destinations within this sunny region at your own pace, making it ideal for discovering hidden gems around your winter rentals.
  • Public Transit: Buses and commuter trains provide affordable and convenient transportation options that connect major cities and scenic areas here, allowing easy access from your stay.
  • Taxi and Rideshare Services: Taxis and popular rideshare apps offer quick, on-demand transportation for short trips or excursions without the hassle of parking or driving yourself.
  • Water Taxis and Ferries: When located near coastal or island destinations, water taxis and ferries serve as scenic and practical ways to reach different parts of the area comfortably and efficiently.

Local Customs Options

  • Respect for Local Wildlife: When enjoying the natural beauty of the region, it’s important to observe local wildlife from a distance and avoid disturbing their habitat.
  • Greeting Etiquette: Friendly nods or handshakes are customary when meeting new neighbors or locals, reflecting the area's warm community spirit.
  • Beach Customs: It’s customary to clean up after yourself on local beaches, ensuring the pristine environment remains enjoyable for everyone.
  • Tipping Practices: Tipping around 15-20% at restaurants and for services is standard here, supporting the hardworking local service industry.

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 211982 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?

The cancellation policy varies depending on the individual listing. You should review the specific terms outlined in the property description or contact the owner directly to understand the refund eligibility and any applicable fees.

4. How do I confirm the availability of a winter rental in Florida?

Availability can be checked by contacting the property owner through the listing platform. It's recommended to inquire early to secure your preferred dates, especially during peak season.

5. Are pets allowed in winter rentals in Florida?

Pet policies differ by property. Please read the listing details carefully or reach out to the owner to confirm if pets are permitted and whether any additional fees or restrictions apply.

6. What amenities are typically included in Florida winter rentals?

Most rentals offer essential amenities such as Wi-Fi, fully equipped kitchens, heating or air conditioning, and outdoor spaces. For specifics, please review the property’s listing description or contact the owner directly.

7. How do I handle payment and safety deposits for my winter stay?

Payment methods and deposit requirements vary per property. It is advisable to verify these details with the owner prior to booking and ensure the platform provides a secure transaction process for your peace of mind.

More Rentals You May Like Near Florida

More Top-Rated Winter Rental in Florida Area