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Compare 1058 Vacation Homes in Key West with updated reviews, rates, and availability.

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (191)
"Very spacious property with plenty of room for 2 couples. Came with pool towels a keurig and a coffee pot, washer and dryer. Walk right out onto duval and 10 minute walk to all the action spots. The pool area is very nice and the porch was nice retreat from afternoon sun. It’s close enough to everything but far enough from nightlife that you don’t get the loud mouths at 2 am. Highly recommend! "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (95)
"Had a blast. Great location and accommodation "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

4-11 to 4-16 Special 195 lodg.+ close beach with 4 night stay by

9.0 out of 10, Wonderful, (161)
"The place was cute; we had everything we needed and it was convenient to all the fun w/o being too close to all the noise and busyness of Duval St. Loved it!"
4-11 to 4-16 Special 195 lodg.+ close beach with 4 night stay by

Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (214)
"This property is centrally located and we easily biked around to everything. There were restaurants and a gas station in walking distance. The surrounding neighborhood is quiet and neighbors were friendly and quiet. The bed was so comfortable, and the adjustable head of bed was so nice! I feel the price may have been on the high side due to Spring Break. I’d like to stay again and hope the price may be more reasonable in other times of the year.Overall, we loved the place and the location."
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (43)
"We just needed a place for a couple of nights so that we could make the day trip to Dry Tortugas NP. This fit the bill! It wasn’t fancy but we felt safe and were easily able to fit our family of 5. But I wouldn’t have stayed for longer than 2 nights as we would’ve been cramped. We had everything we needed and all the necessary instructions ahead of time. And the view off of the back deck was pretty incredible! Also, if you don’t have a sound machine, be prepared for a rooster alarm clock!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (126)
"We've stayed at this property 3 times and we love it. Prefect size. Great communication "
Captain's Daughter: Oversized home for the whole family w/private pool & dock

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

9.6 out of 10, Exceptional, (77)
"We loved staying at this house! Truly an oasis in Key West - privacy, pool and pool setting was awesome, easy to walk to everything Key West has to offer! Everything was clean, comfortable and equipped with everything we needed. Can't wait to go back!"
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (179)
"Nothing but great things to say about the house, location and communications with property managers. And what's not to like about having 3 bathrooms, especially with a larger family like ours. Just walk in and start enjoying key west. It's half a block from Duval St. and about a 5 minute walk to Southern Most."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (18)
"The property was as described. The location was perfect and quiet. We'd love to the pool and hanging out there. Customer service was outstanding."
The price is SAR 1,311
SAR 3,229 total
includes taxes & fees
20 Apr - 21 Apr
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

9.8 out of 10, Exceptional, (216)
"The house had everything we needed. Convenient location. "
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (182)
"Absolutely a gorgeous property and fantastic location. Key West is our favorite place to visit. This house, along with the property manager, made this year's visit the best yet! Thanks for a great birthday and we look forward to booking this property again next year"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

10.0 out of 10, Exceptional, (14)
"We loved our location, the house and Key West!"
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.8 out of 10, Exceptional, (81)
"This was the perfect place for our family to stay. It was very clean and great location. We will be back for sure!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (168)
"This home is fully dialed in. Beautiful finishings, all the towels, sunscreen, and pool accessories you could ask for, and a perfect layout with gorgeous private pool and beautifully landscaped backyard space. Would definitely stay here again!"
The price is SAR 3,754
SAR 7,321 total
includes taxes & fees
13 May - 14 May
Perfect Location, Private Heated Pool & Pristine Luxury Home!

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

10.0 out of 10, Exceptional, (82)
"Location. Location. Location. One block off Duval St and near everything. We rented a car but didn’t need it. Walked everywhere. "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

9.8 out of 10, Exceptional, (146)
"This property is amazingly situated and very well appointed. We have stayed here several times, and it does not disappoint in any respect. The convenience of location (and parking) is amazing and cannot be beat. It's enough off the main street to be comfortably quiet, but you can still enjoy the live music at a level which does not impede conversation while outside. Super clean with high end finishes. The private pool is mostly shaded, which is wonderfully refreshing after being out and about."
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (86)
"Sam, Charlie and Vic were great"
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (76)
"Excellent location, very clean and tastefully decorated. Easy check in. 4 adults so plenty of room. Bedrooms upstairs, mattresses are not very comfy but for a couple nights its fine. Just watch your head with the sloped ceilings!"
The price is SAR 1,483
SAR 3,153 total
includes taxes & fees
29 Apr - 30 Apr
Luxury two floor apartment in prime location of famous Duval Street

Poolside Cottage #412

9.6 out of 10, Exceptional, (22)
"Nice condo. Great location.Would have preferred a king size bed though."
The price is SAR 841
SAR 1,417 total
includes taxes & fees
20 Apr - 21 Apr
Poolside Cottage #412

Conch Cove - 3br/3ba with private heated pool and private parking

9.4 out of 10, Exceptional, (10)
"Everything from the check in process to bedroom and pool amenities were fantastic and everything you would want in a downtown Key West stay. Within walking distance to all the best restaurants and shops with a great outdoor oasis to cool off in after a long day of fun."
The price is SAR 3,000
SAR 6,061 total
includes taxes & fees
20 Apr - 21 Apr
Conch Cove - 3br/3ba with private heated pool and private parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (128)
"Would definitely stay here again! "
The price is SAR 436
SAR 1,120 total
includes taxes & fees
23 Apr - 24 Apr
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (292)
"We both loved the place. Great location, room was awesome, the pool was fun and staff was very friendly and helpful. "
The price is SAR 1,133
SAR 1,380 total
includes taxes & fees
17 Apr - 18 Apr
Hyatt Vacation Club at Sunset Harbor, Key West

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
Heart of Downtown Key West Cottage With Off-Street Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.