Winter Rentals in Florida Keys

Stay in a Winter Rentals in Florida Keys – Plan Your Next Vacation to Florida Keys Today!

Find the Best Winter Rentals for Your Florida Keys Trip

Smartours makes it easy to discover stays that match your style, budget, and location.

  • Winter Rentals
  • Luxury Winter Rentals
  • FAMILY FRIENDLY Winter Rentals
  • PET-FRIENDLY Winter Rentals
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8.8 (139 Reviews)
Bed & Breakfast
Amsterdam's Curry Mansion Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
|
8.8 (139 Reviews)
Bed & Breakfast
Amsterdam's Curry Mansion Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
VIEW ALL RENTALS

Top Rated Activities & Tours in Florida Keys

Key West Shark and Wildlife Catamaran Family-Friendly Tour
Key West Shark and Wildlife Catamaran Family-Friendly Tour
10
Excellent
3207 Reviews
5 star rating Recommendation
From
US $99 Per Person
Reserve
Shark and Wildlife Viewing Adventure in Key West
Shark and Wildlife Viewing Adventure in Key West
10
Excellent
3220 Reviews
5 star rating Recommendation
From
US $99 Per Person
Reserve
Old Town Key West Guided Bicycle Tour
Old Town Key West Guided Bicycle Tour
10
Excellent
2701 Reviews
5 star rating Recommendation
From
US $43 Per Person
Reserve
Guided Bike Tour of Old Town Key West
Guided Bike Tour of Old Town Key West
10
Excellent
2702 Reviews
5 star rating Recommendation
From
US $59 Per Person
Reserve

Why Book Your Trip to Florida Keys with Smartours?

Here’s why smart travelers plan travel with Smartours

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Smarter Stays

Winter Rentals selected for comfort, location and value – giving you the ideal base for your adventures.
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Smarter Itineraries

AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
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Smarter Exploration

Self-guided itineraries filled with local insights, hidden gems, and authentic experiences beyond the typical tourist trail.

How to Book Your Stay in Florida Keys?

What’s the Smartours booking process?

Our platform connects you to a curated selection of Winter Rentals in Florida Keys. Once you’ve found your ideal property, you’ll be redirected to our trusted booking partner to complete your reservation securely and with confidence.

Booking Steps

01

Search Stays

Use Smartours filters to find accommodations that match your style, location preferences, and budget.
02

View Details

Click on a listing to see photos, amenities, reviews, and pricing.
03

Book Securely

Follow the link to finalize your reservation directly with our verified booking partner.
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Indoor Features

  • Fully equipped kitchens or kitchenettes
  • Comfortable living areas with smart TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-room coffee and tea facilities
  • Premium bedding for restful nights
  • Modern bathrooms with walk-in showers or soaking tubs

Outdoor Amenities

  • Balconies, terraces, or rooftop lounges with scenic views
  • Swimming pools, either private or shared
  • Outdoor dining spaces with BBQ or grill access
  • Gardens or courtyards for relaxing downtime
  • On-site parking or easy transport access
  • Proximity to key attractions, markets, or nature trails

Other Places to Stay in Florida Keys

|
8.8 (139 Reviews)
Bed & Breakfast
Amsterdam's Curry Mansion Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
Explore more accommodations

Seasonal Weather in Florida Keys

What’s the weather like in Florida Keys throughout the year?

Florida Keys’s climate varies by region, but most areas enjoy mild to warm weather year-round. Coastal cities benefit from ocean breezes, while inland areas and the desert see greater temperature swings between day and night.

Wednesday May 20

Florida Keys, Florida

Wed
weather-icon
27.9°C
Thu
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27.7°C
Fri
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27.7°C
Sat
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27.8°C
Sun
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28.4°C
Mon
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28.3°C
Tue
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28.4°C

Frequently Asked Questions

What are the top rated Winter Rentals in Florida Keys?
How much does it cost to rent a place to stay near Florida Keys in the wintertime?

The average cost for winter rentals in Florida Keys is $617 per night. Smartours has a wide list of great winter places to stay near Florida Keys that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Florida Keys that allow pets?
Do you have any winter rentals in Florida Keys that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Florida Keys to find what works for you.

Are there winter accommodations in Florida Keys that have indoor swimming pools?

As of 2026, the data from Smartours shows that there are over 8114 private swimming pools or indoor pools accommodations near Florida Keys along with other great amenities.

More Winter Rentals You May Like for Trips to Florida Keys

|
8.8 (139 Reviews)
Bed & Breakfast
Amsterdam's Curry Mansion Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
Explore more accommodations