Holiday Homes in Key West

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Featured Holiday Homes in Key West and around

Our top choices for Key West holiday homes

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

9.8 out of 10, Exceptional, (187)
"Seamless process, great communication. Loved the house. Clean, quiet and close to everything. Thoroughly enjoyed our stay and I would highly recommend!"
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

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

10.0 out of 10, Exceptional, (4)
"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!

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

9.8 out of 10, Exceptional, (226)
"Such a perfect location! Great stay!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

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

9.8 out of 10, Exceptional, (219)
"We had a great time and loved the property "
CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (172)
"This place was perfect for me and my boyfriend! It was in a great area very convenient and parking was pretty easy to find nearby, the new updates were super nice and everything was really clean! Host was really nice and understanding, would definitely stay here again!"
Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio

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

8.8 out of 10, Excellent, (57)
"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!

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

9.8 out of 10, Exceptional, (79)
"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!

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

9.8 out of 10, Exceptional, (88)
"Perfect location, clean, quiet for being so close to everything. Looking to staying here again"
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!

3-Story spacious conch style home w/ private pool & dock!

9.8 out of 10, Exceptional, (132)
"We had a wonderful stay in Key West and this house was great for everything we needed!"
3-Story spacious conch style home w/ private pool & dock!

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.6 out of 10, Exceptional, (44)
"What a great stay! We’ll be back!"
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

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

9.2 out of 10, Wonderful, (52)
"Amazing place "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (213)
"The house was quiet yet convenient to many attractions and restaurants. The property manager couldn’t have been better or more attentive to us. It’s close to a golf cart rental place for when you get tired of walking and to the Trolly. "
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (135)
"Beautiful home with everything needed for a fun family vacation"
Oversized home for the whole family w/private pool & dock

Coastal Comfort & 3/4 Time Compound

Coastal Comfort & 3/4 Time Compound

**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES

10.0 out of 10, Exceptional, (44)
"Great property location. Has everything we needed for a family vacation! "
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

9.4 out of 10, Exceptional, (21)
"Great location and communication with the property management."
The price is €247
includes taxes & fees
29 Sept - 30 Sept
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

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

9.2 out of 10, Wonderful, (80)
"Great location! Close to all the activities."
The price is €910
includes taxes & fees
28 Sept - 29 Sept
Spacious home with pool & balcony - 1 block from Duval Street

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

9.6 out of 10, Exceptional, (76)
"Beautiful house "
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping

Wahoo Way | Charming Hideaway On Duval Street!

9.0 out of 10, Wonderful, (17)
"Very convenient to everything! We throughly enjoyed our stay. The rides from and to the airport were an extra bonus."
The price is €223
includes taxes & fees
29 Sept - 30 Sept
Wahoo Way | Charming Hideaway On Duval Street!

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

9.8 out of 10, Exceptional, (78)
"Nice place. "
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
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

Find out more about Key West

Find out more about Key West

Key West Holiday Homes information

Number of reviews
1,348
Accommodation
1055 Holiday Homes
Lowest Price
€223
Highest Price
€910