Holiday Homes in Key West

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Key West and around

Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Terrace/patio

Seaside Retreat: Waterfront Home with private heated pool & lush landscaping

9.6 out of 10, Exceptional, (75)
"Beautiful house "
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
A heated pool

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (3)
"Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had."
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds

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

8.8 out of 10, Excellent, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
A heated pool

Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool

9.0 out of 10, Wonderful, (57)
"We had a wonderful stay. The layout of the property was perfect for our group of 8. The pool and the rooftop patio were perfect. The property manager was also very responsive to any questions we had."
Amelia's Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
A heated pool

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

9.8 out of 10, Exceptional, (218)
"We had a great time and loved the property "
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
Terrace/patio

Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (170)
"This was a great location and easy place to stay. We were able to walk to many locations in Old Town. The new updates are a nice addition to this location. Fresh paint, refrigerator, A/C and the patio is a great place to relax. "
Spec @107.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.4 out of 10, Exceptional, (49)
"Clean, home included everything you could need. Best of all, communication was clear, friendly, professional and a binder was left with activities, restaurants, etc. Parking spot was clear and easy. Beautiful stay"
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Outdoor dining

KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

9.8 out of 10, Exceptional, (78)
"We were so happy with our stay! It was clean, easy and in a great spot! Highly recommend this place. "
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Oceanview home with private pool & lush landscaping!
A heated pool

Oceanview home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (114)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Oceanview home with private pool & lush landscaping!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
A heated pool

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

9.8 out of 10, Exceptional, (88)
"Great location "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
Kingfish Keep | Lively Escape on Duval! Balcony!
Living area

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (18)
"Awesome location with excellent communication. "
Kingfish Keep | Lively Escape on Duval! Balcony!
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (191)
"Great place. well located. Will be returning."
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (186)
"The location was excellent—just a short walk to Duval Street. The property was spacious enough to comfortably accommodate our family of five, and having three bathrooms was a big plus."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
Outdoor pool, a heated pool

PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (213)
"Wonderful stay here for our family. Great price and close to Key West!"
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
A heated pool

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

9.8 out of 10, Exceptional, (225)
"Such a perfect location! Great stay!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool

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

9.8 out of 10, Exceptional, (102)
"We had a wonderful stay. The house was perfect. Plenty of privacy yet we were steps away from all that duval st has to offer. Super clean, super nice, perfect for our family. Highly recommend!"
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Tropical Key West out of the way
Pool

Tropical Key West out of the way

9.4 out of 10, Exceptional, (173)
"Great location and overall experience. "
Tropical Key West out of the way
Spacious home with pool & balcony - 1 block from Duval Street
TV, stereo

Spacious home with pool & balcony - 1 block from Duval Street

9.2 out of 10, Wonderful, (79)
"Location and pool were great! No washer/Dryer, no ice maker, shared bathroom was very small and beds were saggy. "
Spacious home with pool & balcony - 1 block from Duval Street
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental
Fridge, microwave, oven, stovetop

Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental

10.0 out of 10, Exceptional, (6)
Meadows Manor | Elegant Oasis with Private Pool & Parking! Weekly Rental
Passover Cottage | Private Pool & Ideal Key West Location
Dining

Passover Cottage | Private Pool & Ideal Key West Location

9.6 out of 10, Exceptional, (4)
"We had a short stay but it was wonderful. The home is a super unique, well restored conch home. The pool and backyard area is private and beautiful, loved the pool. This property was perfect for our needs! We would absolutely stay there again and recommend it to anyone. "
Passover Cottage | Private Pool & Ideal Key West Location
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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Top Key West Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The entire staff was very nice and accommodating, we always had close convenient parking. We were very close to things we wanted to do on the water and staff was very helpful with the local attractions. We would stay again and again.... 2 thumbs up"
Michael 4-night trip
Posted 8 hours ago
Beachside Resort & Residences