Key West, FL Vacation Homes from AED 3,133

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Our top choices for Key West vacation homes

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Old Town Key West

Kristin E.

Poolside Cottage #411

Key West

Tiara B.

AED 1,459 total

includes taxes & fees

10 Jul - 11 Jul

Road's End | Prime Old Town Location! Updated Home w/ Pool

Old Town Key West

Mike T.

AED 1,856 total

includes taxes & fees

13 Jul - 14 Jul

Shared Pool & Near Duval - Curry House Room 9

Old Town Key West

"Definitely an adorable place to stay! The host was very accommodating with any questions we had, especially when our flight arrived earlier than planned. Great location for walking to Duval Street and many other great places. Our room was very small but we knew that before staying. Dont suggest this room for anyone over 5'7 ... lol. Still was perfect for us though. Clean, friendly staff, quiet. Would definitely stay here again."

Christin M.

AED 1,202 total

includes taxes & fees

23 Jun - 24 Jun

Poolside Cottage #412

Key West

Julia M.

AED 1,459 total

includes taxes & fees

10 Jul - 11 Jul

Paradise found

Stock Island

Robert B.

AED 2,197 total

includes taxes & fees

23 Jun - 24 Jun

Sea Esta Suite | Located On Iconic Duval w/ Pool

Old Town Key West

Colleen S.

AED 3,089 total

includes taxes & fees

28 Jun - 29 Jun

Atlantis House Suites

Midtown

Aaron J.

AED 2,331 total

includes taxes & fees

23 Jun - 24 Jun

Luxury two floor apartment in prime location of famous Duval Street

Old Town Key West

Tracy M.

AED 2,634 total

includes taxes & fees

23 Jun - 24 Jun

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Stock Island

Nathan W.

AED 3,631 total

includes taxes & fees

23 Jun - 24 Jun

Casa Havana | Old Town Condo w/ Pool & Balcony

Old Town Key West

"The property is very old, run down, furniture needs to be replaced, entire interior and trim needs to be repainted, paint chipped off of the majority of trim and molding, significant number of ants in both bedroom bathrooms, mattresses need to be replaced as they are soft and worn out, and not least of all, the property manager has hidden the thermostat underneath an alarm cover, seemingly to prevent guests from lowering the temperature."

John B.

AED 2,743 total

includes taxes & fees

15 Jul - 16 Jul

Southernmost Retreat | On Duval! With Hot Tub, Patio

Old Town Key West

Stephen S.

AED 3,677 total

includes taxes & fees

28 Jun - 29 Jun

Passover Cottage | Private Pool & Ideal Key West Location

Old Town Key West

john w.

AED 3,073 total

includes taxes & fees

28 Jun - 29 Jun

3-bedroom townhome in Key West with fitness room, WiFi

Stock Island

Trisha K.

AED 3,986 total

includes taxes & fees

23 Jun - 24 Jun

Key West Lighthouse Suite

Old Town Key West

Andy S.

AED 3,764 total

includes taxes & fees

24 Jun - 25 Jun

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Key West Historic District

Edward M.

AED 5,053 total

includes taxes & fees

23 Jun - 24 Jun

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Old Town Key West

Brandon A.

AED 4,306 total

includes taxes & fees

27 Jun - 28 Jun

Private Parking, Heated Pool - Sweet Caroline

Key West Historic District

Jenny R.

AED 3,016 total

includes taxes & fees

29 Jun - 30 Jun

Spacious 3-bedroom townhome on Stock Island with resort style pool.

Stock Island

janet n.

AED 2,718 total

includes taxes & fees

12 Jul - 13 Jul

Steps to Duval •Hot tub • Sleeps 6

Old Town Key West

Kat B.

AED 2,572 total

includes taxes & fees

24 Jun - 25 Jun

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Top Key West Hotel Reviews

Southwinds Motel

10/10 Excellent

"Todo limpio."

The Perry Hotel & Marina Key West

8/10 Good

"Nice hotel. 5 days/4 nights stay. Free parking, but no free breakfast The room came with a fridge and a coffee maker, no microwave. 2 Restaurants in the property, but food is very expensive. Staff at check in don’t even smile at you, when they do it feels forced. Concierges were very nice. The shuttle to Key West is a great feature. One of the two pools was closed. The one pool was packed full every day. Room was great. Tile on the floors, hubby found bed uncomfortable. Our room had one King bed and a coffee table. It felt unfinished. It needs a small sofa or something, so you don’t have to use the bed to sit to eat or work on your laptop. Every room has a very spacious balcony. The gym is very well equipped."

Blue Flamingo Resort Key West

8/10 Good

"The food was amazing! There was a language barrier for the maid staff, but most were very nice. The last three days the place was overrun by little league baseball players and their families. The lobby was packed with screaming, horseplay all hours and both pools were overcrowded with kids as well. The pool was not maintained well and was full of hair and bugs. Overall, fantastic experience."

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good

"Property was very clean and maintained. Pool was nice and clean. Pool Bar had limited hours. Breakfast was good for a free hotel breakfast. The beach amenities in resort free were great and useful. The shuttle was nice and easy to use. Some say rooms are small but I found to be normal size and on newer side of remodeled. Tough to predict time they come by to clean room so we did miss a few days. Ride everywhere was only few minutes but not walkable"

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"The resort itself was beautiful, and our room was spacious and comfortable. The property has a lot to offer, and we were looking forward to a relaxing vacation. Unfortunately, the first three nights of our stay were anything but relaxing due to a business event being held at the resort. Our room was located above or near the ballroom, and we could hear the loud bass from the music being played during the events. The noise carried into our room late into the night and made it difficult to relax. We complained to the front desk and the first response was that they would ask the event to turn down the music. The second response was this happens a lot when events are held here. The third response was from the security staff who got us a room credit which we appreciated but it was not his job to do what management should have done. To make matters worse, on our very first morning we were awakened at 6:30 a.m. by the same music. Throughout our stay, various event-related activities around the resort created additional disruptions that took away from the peaceful atmosphere we had expected. While the resort and our accommodations were excellent, the noise and disturbances associated with the business event significantly impacted our experience. Guests seeking a quiet, relaxing vacation may want to inquire about scheduled conferences or large events before booking."

Search Vacation Homes in Key West

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Key West vacation homes

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Poolside Cottage #411

Road's End | Prime Old Town Location! Updated Home w/ Pool

Shared Pool & Near Duval - Curry House Room 9

Poolside Cottage #412

Paradise found

Sea Esta Suite | Located On Iconic Duval w/ Pool

Atlantis House Suites

Luxury two floor apartment in prime location of famous Duval Street

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Casa Havana | Old Town Condo w/ Pool & Balcony

Southernmost Retreat | On Duval! With Hot Tub, Patio

Passover Cottage | Private Pool & Ideal Key West Location

3-bedroom townhome in Key West with fitness room, WiFi

Key West Lighthouse Suite

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Private Parking, Heated Pool - Sweet Caroline

Spacious 3-bedroom townhome on Stock Island with resort style pool.

Steps to Duval •Hot tub • Sleeps 6

Find vacation rentals that suit your style

Top Key West Hotel Reviews

Southwinds Motel

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