Trips to Old Town

Plan Your Next Trip to Old Town and explore unforgettable sights, local flavors, and exciting experiences.

Find the Best Accommodations for Your Old Town Trip

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

  • Hotels
  • Villas
  • Cabins
  • apartments
  • Cottages
  • Resorts
  • Ski chalets
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8.6 (418 Reviews)
Hotel
Aqua Lodges At Hurricane Hole Marina
  • Air Conditioner
  • Parking
  • Designated Smoking Area
US
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10 (3 Reviews)
Apartment
Keys Livin - Yacht Rental
  • Air Conditioner
  • Parking
  • Pet Friendly
US
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|
9.4 (132 Reviews)
Bed & Breakfast
Andrews Inn & Garden Cottages
  • Air Conditioner
  • Parking
  • Pool
US
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Top Rated Activities & Tours in Old Town

Key West Shark and Wildlife Catamaran Family-Friendly Tour
Key West Shark and Wildlife Catamaran Family-Friendly Tour
10
Excellent
3136 Reviews
5 star rating Recommendation
From
US $99 Per Person
Reserve
Key West Mangrove Kayak Eco Tour
Key West Mangrove Kayak Eco Tour
10
Excellent
2303 Reviews
5 star rating Recommendation
From
US $80 Per Person
Reserve
Key West Small-Group Food and Culture Walking Tour With Drink
Key West Small-Group Food and Culture Walking Tour With Drink
10
Excellent
1831 Reviews
5 star rating Recommendation
From
US $90 Per Person
Reserve
Key West: Half-Day Sailing Tour With Kayaking and Snorkeling
Key West: Half-Day Sailing Tour With Kayaking and Snorkeling
10
Excellent
1735 Reviews
5 star rating Recommendation
From
US $125 Per Person
Reserve
See More Activities & Tours in Old Town

Why Book Your Trip to Old Town with Smartours?

Here’s why smart travelers plan travel with Smartours

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Smarter Stays

Hotels, villas, and vacation 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 Old Town?

What’s the Smartours booking process?

Our platform connects you to a curated selection of hotels, villas, and unique stays in Old Town. 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 Old Town

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Seasonal Weather in Old Town

What’s the weather like in Old Town throughout the year?

Old Town’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.

Thursday Apr 23

Old Town, Key West

Wed
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24.7°C
Thu
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23.9°C
Fri
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23.7°C
Sat
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24.0°C
Sun
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24.6°C
Mon
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25.1°C
Tue
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25.1°C

Map of Old Town

Frequently Asked Questions

What are the top vacation rentals in Old Town?
How many vacation rentals have private pools in Old Town?
Which vacation homes in Old Town are best for families?

If you are looking for a family-friendly vacation home in Old Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Town:

How many vacation rentals are available in Old Town?

Currently, the total number of properties listed in 2026 is over 3652 in the Old Town area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Old Town.

More Accommodations You May Like for Trips to Old Town

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