Cottages in Key West

Stay in a Cottages in Key West – Plan Your Next Vacation to Key West Today!

Find the Best Cottages for Your Key West Trip

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

  • Cottages
  • Luxury Cottages
  • FAMILY FRIENDLY Cottages
  • PET-FRIENDLY Cottages
9.2 (21 Reviews)
Cottage
Find your zen at HIDDEN TREASURE
  • Air Conditioner
  • Parking
  • Pet Friendly
US
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9.3 (4 Reviews)
Apartment
Atocha Cottage - Harbor Walk Hideaways
  • Pet Friendly
  • Security/Safety
  • Child Friendly
US
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9.6 (101 Reviews)
Cottage
HIDDEN OASIS 3 blocks from Duval
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.6 (84 Reviews)
Cottage
Get your ISLAND STLYE on!
  • Air Conditioner
  • Parking
  • Pet Friendly
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Top Rated Activities & Tours in Key West

Key West Shark and Wildlife Catamaran Family-Friendly Tour
Key West Shark and Wildlife Catamaran Family-Friendly Tour
10
Excellent
3343 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
3343 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
2723 Reviews
5 star rating Recommendation
From
US $59 Per Person
Reserve
Guided Bike Tour of Old Town Key West
Guided Bike Tour of Old Town Key West
10
Excellent
2723 Reviews
5 star rating Recommendation
From
US $59 Per Person
Reserve

Why Book Your Trip to Key West with Smartours?

Here’s why smart travelers plan travel with Smartours

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Smarter Stays

Cottages 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 Key West?

What’s the Smartours booking process?

Our platform connects you to a curated selection of Cottages in Key West. 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 Key West

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Seasonal Weather in Key West

What’s the weather like in Key West throughout the year?

Key West’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.

Sunday Jul 26

Key West, Florida

Sat
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29.6°C
Sun
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29.2°C
Mon
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29.0°C
Tue
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29.0°C
Wed
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29.1°C
Thu
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29.1°C
Fri
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29.3°C

Frequently Asked Questions

What are the top rated Cottage Rentals in Key West?
How much does it cost to rent a cottage in Key West?

The average cost for a cottage rental in Key West is $453 per night. Smartours has a wide list of great cottages near Key West that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Key West that allow pets?
Do you have any rental cottages in Key West that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Key West to find one that works for you.

Are there quality cottages in Key West that have indoor swimming pools?

As of 2026, the data from Smartours shows that there are Over 133 private swimming pools or cottages with indoor pools in the Key West area along with other great amenities.

More Cottages You May Like for Trips to Key West

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