Fire table and sitting area near pool watching boats pass through canal.

Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

4 bedrooms·4 baths
5(9 reviews)
$455/ night(excl. fees & taxes)
Casa West Indies

Casa West Indies

2 bedrooms·2 baths
$400/ night(excl. fees & taxes)
Keys Waterfront- Spectacular Gulf View, Dock, Pool

Keys Waterfront- Spectacular Gulf View, Dock, Pool

3 bedrooms·1 bath
4.5(10 reviews)
$285 – $429/ night(excl. fees & taxes)
Huge seasonally heated pool

Cathouse Old Town Oasis Huge Heated Pool & Parking

4 bedrooms·2½ baths
5(72 reviews)
$465 – $2,905/ night(excl. fees & taxes)
Kittyhouse on Catherine, Tropical Pool, Parking

Kittyhouse on Catherine, Tropical Pool, Parking

2 bedrooms·1½ baths
$260 – $293/ night(excl. fees & taxes)
Private tropical plunge pool with waterfall and sunny brick patio

Cockhouse 3BR/3BA Privt Pool/Parking/Pets Old Town

3 bedrooms·3 baths
5(1 review)
$180 – $617/ night(excl. fees & taxes)
Garden Apartment Sanctuary in Historic District

Garden Apartment Sanctuary in Historic District

0 bedrooms·1 bath
5(7 reviews)
$89 – $241/ night(excl. fees & taxes)
Old Town Gated Studio, Great Location, Great Value

Old Town Gated Studio, Great Location, Great Value

0 bedrooms·1 bath
5(6 reviews)
$89 – $366/ night(excl. fees & taxes)
Sunny tropical patio with bistro set, grill & French doors

Beach House Modern Old Town Studio Near Duval

1 bedroom·1 bath
$90 – $448/ night(excl. fees & taxes)
Welcome to Stay Anchored at Sombrero. View from across the canal.

Stay Anchored at Sombrero

4 bedrooms·3 baths
5(19 reviews)
$470/ night(excl. fees & taxes)
Coral Palms 1BR/King/Queen, Pool, block to Duval

Coral Palms 1BR/King/Queen, Pool, block to Duval

1 bedroom·1 bath
5(64 reviews)
$193 – $1,262/ night(excl. fees & taxes)
Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool

Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool

2 bedrooms·2 baths
5(1 review)
$136 – $370/ night(excl. fees & taxes)
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.

Casa Rosa: Historic Key West Home with Pool, 1 Block from Duval

4 bedrooms·4 baths
5(9 reviews)
$558 – $1,375/ night(excl. fees & taxes)
Breathtaking open views of the Gulf of America, right from your private dock

Caribbean Sunsets: Open Gulf Views with Private Dock and Pool

3 bedrooms·3 baths
5(4 reviews)
$380 – $930/ night(excl. fees & taxes)
Marathon Gulfside Lake view home, bring your boats

Marathon Gulfside Lake view home, bring your boats

4 bedrooms·3½ baths
$1,000/ night(excl. fees & taxes)
Open Gulf Views with Private Pool and Dock

Tropical Sunsets: Open Gulf Views with Private Dock and Pool

4 bedrooms·3 baths
5(4 reviews)
$430 – $1,058/ night(excl. fees & taxes)
Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub

Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub

3 bedrooms·2 baths
4.9(29 reviews)
$150 – $389/ night(excl. fees & taxes)
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

3 bedrooms·2 baths
4.94(16 reviews)
$375/ night(excl. fees & taxes)
Paradise Found!

Paradise Found!

3 bedrooms·2 baths
5(3 reviews)
$340 – $530/ night(excl. fees & taxes)
Enjoy your own private movie theater, promising cinematic magic in a serene ambiance under the stars. You can also dip into your own private hot tub and enjoy a movie, the stars and the calm & private twilight hues

Keys Getaway - Pool, Hot Tub & Movie Theater

3 bedrooms·3 baths
$170 – $1,175/ night(excl. fees & taxes)
View of Cove from Backyard

Waterfront Keys Home - Spectacular View, 37' Dock

2 bedrooms·2 baths
4.33(3 reviews)
$169 – $249/ night(excl. fees & taxes)
A View from the Backyard

Waterfront Home - Incredible View, 37' Dock, Kayak

2 bedrooms·2 baths
4.77(13 reviews)
$169 – $239/ night(excl. fees & taxes)
Private Pool & Tiki Hut

Tropical Pool Home - Tiki Hut & 60' Dock

2 bedrooms·2 baths
$272 – $429/ night(excl. fees & taxes)