Best Key West Vacations

Find out what Key West has in store for vacationers, from unique annual events to sunken treasures. For the best Key West vacations, turn to HomeAway.

Key West Rentals

Truman Annex Best Location in Town

Greetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita. 'Margarita Villas' are located in historic Old Town in a beautiful, very private gated com...

'Casa Coral' Relaxing Key West Townhome In Gated Community, Sleeps 6

Fully remodeled 2 bedroom, 2.5 bathroom, 2 level Key West townhome to be your home away from home! No detail has been overlooked in the bright and airy vacation rental. Located in one of the islands newest gated community’s, Coral Hammock, you a...

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

A unique feature of this property is bicycles! Key West is only two miles by four miles, so nothing is very far away. Fly into the Key West airport and take a cab to Truman Annex You have bicycle transportation throughout your vacation. Big basket...

STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN

WALK EVERYWHERE! LOCATED STEPS FROM DUVAL, YOU ARE WALKING DISTANCE TO SHOPS, RESTAURANTS, & BARS. SOUTHERNMOST BEACH IS JUST 3 SHORT BLOCKS AWAY. THE 'BELLA VITA' IS A TOTALLY RENOVATED CONDO ON THE FIRST FLOOR. SHE IS TH...

Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex

Enjoy all the charm Key West has to offer in this beautiful, newly renovated 4 bedroom/3 full bath house with private heated pool in the heart of Old Town. This home has ample room for relaxation and enjoyment. Located in the gated community of Tr...

Vacation Home Search

Find the perfect rental for your vacation

Join Our Newsletter

Get the latest updates in your email