Top Vacation Rentals in Key West ᐅ Instant booking

Cottage for 4 people, with terrace and pool - 1

Exclusive Key West Beach Front - 2Br Luxury Condo w/Gym and Pool Access (Newly Refurnished!)

Sleeps 6 pers.2 bedrooms1,894 ft²

PoolBalconyParkingInternet

~ Solaris Cottage ~ Live like a local in this bright and cozy retreat.

Sleeps 2 pers.1 bedroom527 ft²

YardTerraceInternet

2 more units available

Sea Breeze - One Block from Duval Street

Sleeps 6 pers.2 bedrooms797 ft²

BalconyParkingInternet

Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking

Sleeps 6 pers.2 bedrooms

PoolHot tubBalconyParking

~ Poinciana Treetop ~ Casual second floor duplex 2 blocks from Duval Street!

Sleeps 3 pers.1 bedroom614 ft²

BalconyParkingInternet

One more unit available

Sept. spec @ 125 night lodg. With 4 night stay 4th night lodg. is Free!

Sleeps 2 pers.1 bedroom495 ft²

TerraceParkingInternet

Poolside Queen Room Steps from Duval!

Sleeps 2 pers.1 bedroom194 ft²

PoolHot tubTerraceParking

2 more units available

Sept Special@119.lodging + With 4 night stay 4th night Free lodging!

Sleeps 2 pers.1 bedroom495 ft²

TerraceParkingInternet

By the Beautiful Sea - Key West Beach Front Condo - w Pool Access

Sleeps 6 pers.3 bedrooms1,389 ft²

PoolSaunaHot tubBalcony

New Pricing: Drive To Your Getaway - Big Pool, Steps to Beach & Free Parking

Sleeps 12 pers.5 bedrooms2,691 ft²

PoolBalconyYardParking

Driftwood Dreams Beachside Condo & Pool + Last Key White Glove Service...

Sleeps 6 pers.2 bedrooms1,356 ft²

PoolSaunaHot tubBalcony

2 more units available

Majestic Paradise @ Truman Annex - Heart of Old Town, Key West

Sleeps 5 pers.2 bedrooms700 ft²

PoolYardTerraceParking

Rent a Piece of Paradise, Best Location on the Island!

Sleeps 4 pers.2 bedrooms700 ft²

PoolYardTerraceParking

Blue Bungalow ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

Sleeps 6 pers.2 bedrooms958 ft²

PoolBalconyParkingInternet

Upscale end unit home @ Truman Annex close to Duval St

Sleeps 3 pers.1 bedroom

PoolBalconyParkingInternet

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Sleeps 2 pers.1 bedroom441 ft²

TerraceParkingInternet

Duval Street Suites on Duval Free Parking and heated Pool

Sleeps 4 pers.1 bedroom398 ft²

PoolYardParkingInternet

9 more units available

Sun, Sea & Sky at Truman Annex in Key West

Sleeps 4 pers.1 bedroom592 ft²

PoolBalconyParkingInternet

Dual Balconies + Pool | Walk to Duval + Old Town | Shipyard Treasure

Sleeps 4 pers.2 bedrooms753 ft²

PoolBalconyParkingInternet

A Touch of Bermuda in Key West

Sleeps 6 pers.2 bedrooms1,195 ft²

PoolHot tubBalconyYard

Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

Sleeps 4 pers.2 bedrooms

PoolYardTerraceParking

5 Star Home 4 Br 3/1/2 baths, pool. Extremely discounted for 28 day rental.

Sleeps 8 pers.4 bedrooms1,798 ft²

PoolHot tubYardTerrace

Saltwater Harmony @ The Annex Condo & Pool + Last Key White Glove Service...

Sleeps 4 pers.2 bedrooms678 ft²

PoolBalcony/TerraceParkingInternet

Oyster's Pearl at The Truman Annex in Key West

Sleeps 2 pers.1 bedroom678 ft²

PoolTerraceParkingInternet

Seaport Sanctuary ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!

Royal Palm Studio ~ Adult Only, Studio w/ Community Pool & Close to Town!

Barefoot Bungalow~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!

Colony Calypso - A quaint 1 Bedroom Cottage just two blocks to Duval

Poolside Cottage #411

Conch Cottage - Feels Like Home - 1Bd/1Bath - Hot Tub

Exclusive Key West Beach Front - 2Br Luxury Condo w/Gym and Pool Access (Newly Refurnished!)

~ Solaris Cottage ~ Live like a local in this bright and cozy retreat.

Sea Breeze - One Block from Duval Street

Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking

~ Poinciana Treetop ~ Casual second floor duplex 2 blocks from Duval Street!

Sept. spec @ 125 night lodg. With 4 night stay 4th night lodg. is Free!

Poolside Queen Room Steps from Duval!

Sept Special@119.lodging + With 4 night stay 4th night Free lodging!

By the Beautiful Sea - Key West Beach Front Condo - w Pool Access

New Pricing: Drive To Your Getaway - Big Pool, Steps to Beach & Free Parking

**Driftwood Dreams** Beachside Condo & Pool + Last Key White Glove Service...

Majestic Paradise @ Truman Annex - Heart of Old Town, Key West

Rent a Piece of Paradise, Best Location on the Island!

Blue Bungalow ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

Upscale end unit home @ Truman Annex close to Duval St

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Duval Street Suites on Duval Free Parking and heated Pool

Sun, Sea & Sky at Truman Annex in Key West

Dual Balconies + Pool | Walk to Duval + Old Town | Shipyard Treasure

A Touch of Bermuda in Key West

Two Bed One Bath Ground Floor End Unit in the Heart of Old Town

5 Star Home 4 Br 3/1/2 baths, pool. Extremely discounted for 28 day rental.

**Saltwater Harmony @ The Annex** Condo & Pool + Last Key White Glove Service...

Oyster's Pearl at The Truman Annex in Key West

Driftwood Dreams Beachside Condo & Pool + Last Key White Glove Service...

Saltwater Harmony @ The Annex Condo & Pool + Last Key White Glove Service...