Owner Direct Vacation
Rentals in Old Town

The Best Owner Direct Vacation Rentals in Old Town. Explore thousands of vacation home rentals, large cabins, and villas near Old Town

  1. Owner Direct
  2.  USA
  3.  Florida
  4.  Key West
  5.  Old Town

Explore the Best Old Town Vacation Homes

Looking for the perfect place to stay in Old Town? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Old Town character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos
|
10 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
US
View Availability
|
10 (1 Review)
House
Charming chácara with AC in Key West
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
US
View Availability
|
10 (3 Reviews)
House
Yellowfin Ledge
  • Pet Friendly
  • Security/Safety
  • Child Friendly
US
View Availability
|
10 (2 Reviews)
House
Duval Hideaway
  • Parking
  • Pet Friendly
  • Security/Safety
US
View Availability

Why Travelers Love Using
Owner Direct to
Find Old Town Vacation Rentals

What makes our vacation homes stand out?

check-mark

Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

check-mark

Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

check-mark

Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Popular Neighborhoods for Old Town Vacation Rentals

What are the best areas to stay in Old Town

Discover the top neighborhoods in Old Town and choose a place that suits your stay.

Friday Jan 30

Old Town, Key West

Fri
weather icon
18.8°C
Sat
weather icon
19.2°C
Sun
weather icon
12.2°C
Mon
weather icon
13.0°C
Tue
weather icon
14.9°C
Wed
weather icon
19.3°C
Thu
weather icon
18.9°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Old Town vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

More Vacation Rentals You May Like Near Old Town

How to Reserve Your Old Town Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

search-icon

SEARCH PROPERTIES

Use filters for location, amenities, and budget.

compare-icon

VIEW DETAILS

Check photos, reviews, and features for your top picks.

bed-icon

BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Old Town Vacation Rental FAQs

1. What are the top vacation rentals in Old Town?

2. How many vacation rentals have private pools in Old Town?

3. 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:

4. How many vacation rentals are available in Old Town?

Currently, the total number of properties listed in 2026 is over 3494 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.