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)
$544 – $3,216/ 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)
$231 – $1,505/ night(excl. fees & taxes)
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)
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
5(11 reviews)
$170 – $248/ 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)
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

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

5 bedrooms·5 baths
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)
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)
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
5(5 reviews)
$230 – $484/ 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
$253 – $1,695/ 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(8 reviews)
$558 – $1,375/ 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)
New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!

3 bedrooms·3 baths
$354 – $1,443/ 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
$186 – $1,334/ 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 – $1,030/ 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)
Garden Apartment Sanctuary in Historic District

Garden Apartment Sanctuary in Historic District

0 bedrooms·1 bath
5(6 reviews)
$89 – $259/ 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 – $340/ 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)
Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub

3 bedrooms·3 baths
$354 – $1,997/ night(excl. fees & taxes)
Beautiful Sunrises on the Jetty

Florida Keys Getaway - Huge Pool, Beach, Amenities

1 bedroom·1 bath
$90 – $619/ night(excl. fees & taxes)