Welcome to Stay Anchored at Sombrero. View from across the canal.

Stay Anchored at Sombrero

4 bedrooms·3 baths
5(19 reviews)
$450 – $600/ 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)
Huge seasonally heated pool

Cathouse Old Town Oasis Huge Heated Pool & Parking

4 bedrooms·2½ baths
5(51 reviews)
$614 – $3,460/ 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(52 reviews)
$249 – $1,361/ night(excl. fees & taxes)
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

5 bedrooms·5 baths
Walk to Beach + Dining, 2BR, King Bed

Walk to Beach + Dining, 2BR, King Bed

2 bedrooms·1 bath
$225 – $3,000/ night(excl. fees & taxes)
Modern Coastal Suite | Walk to Beach + Dining

Modern Coastal Suite | Walk to Beach + Dining

1 bedroom·1 bath
$175 – $3,000/ 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)
Sunny Waterfront Key Colony 3BR 3BA Villa w/ Dock

Sunny Waterfront Key Colony 3BR 3BA Villa w/ Dock

3 bedrooms·3 baths
$258 – $1,695/ 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)
$79 – $303/ night(excl. fees & taxes)
Garden Apartment Sanctuary in Historic District

Garden Apartment Sanctuary in Historic District

0 bedrooms·1 bath
5(6 reviews)
$79 – $322/ night(excl. fees & taxes)
Cozy Keys Stay | King Bed + Luxe Bath

Cozy Keys Stay | King Bed + Luxe Bath

1 bedroom·1 bath
$200 – $3,000/ night(excl. fees & taxes)
New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!

3 bedrooms·3 baths
$336 – $1,598/ 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
$430 – $1,058/ night(excl. fees & taxes)
Enjoy a serene walk along the beach, mere steps from your condo.

Coastal Charm: Steps from the Beach, 2BR/2BA Condo, Pool View

2 bedrooms·2 baths
$170 – $248/ night(excl. fees & taxes)
Condo #15, located on the 2nd floor, offers stunning ocean views and has two screened balconies

Bird of Paradise: Oceanfront Condo 3 BR, 2 BA with Heated Pool

3 bedrooms·2 baths
$230 – $484/ 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
$251 – $1,411/ 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
$648 – $1,375/ night(excl. fees & taxes)
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!

3 bedrooms·3 baths
$350 – $1,528/ night(excl. fees & taxes)
Bright and open kitchen and dining area, perfect for cooking meals and gathering around the table. Enjoy all the comforts of home with plenty of space to dine and relax.

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

2 bedrooms·2 baths
$136 – $370/ 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
$380 – $1,030/ night(excl. fees & taxes)
Kittyhouse on Catherine, Tropical Pool, Parking

Kittyhouse on Catherine, Tropical Pool, Parking

2 bedrooms·1½ baths
Private tropical plunge pool with waterfall and sunny brick patio

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

3 bedrooms·3 baths
$189 – $600/ night(excl. fees & taxes)