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

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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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Top Rated Activities & Tours in Florida Keys
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Why Book Your Trip to Florida Keys with Smartours?
Here’s why smart travelers plan travel with Smartours
Smarter Stays
Winter Rentals selected for comfort, location and value – giving you the ideal base for your adventures.
Smarter Itineraries
AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
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
Search Stays
Use Smartours filters to find accommodations that match your style, location preferences, and budget.
View Details
Click on a listing to see photos, amenities, reviews, and pricing.
Book Securely
Follow the link to finalize your reservation directly with our verified booking partner.
Common Trip Amenities in Florida Keys?
What amenities can you expect on your Smartours trip?
Our handpicked Winter Rentals in Florida Keys are chosen for comfort, convenience, and style — often with thoughtful extras to make your trip even more memorable. Here’s what you might look forward to
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
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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







Frequently Asked Questions
There are a lot of options in Florida Keys. If you plan on staying in the Florida Keys 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 Keys:
- Almond Tree Inn Hotel - Adults Only
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Oceanfront Key Largo Paradise~Private Beach~Pool~Tennis~Marina~Cafe/Bar
- Summer Fun Awaits! Clean and Cozy w TOP FLOOR VIEWS.Your Home Away From Home!
- Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
- Sale: May 10-14 & 18-21! Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access
- Key Lime Kottage- Waterfront Home on Gulf of Mexico w/Private Pool, Dock & More
- 🌴 Coco Plum Paradise 🌴 Private Bayfront Home Pool Hot Tub Dock View
- Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
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.
Yes, here are the top cottage/chalet rentals in Florida Keys that allow you to bring your pet or dog:
- Amsterdam's Curry Mansion Inn
- Casita de Catherine by Avantstay 1 Block to Duval St w/Hot Tub!
- Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - WITH Boat Slip!
- LICENSED MGR - MODERN OCEANFRONT - OCEAN VIEWS CONDO! BAR and BEACH RESORT!
See all pet-friendly vacation rentals in Florida Keys on Smartours
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.
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
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