Holiday Homes in Fleming Key

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Fleming Key and around

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

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

9.6 out of 10, Exceptional, (209)
"Outstanding property! Cannot recommend highly enough!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
Terrace/patio

TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!

9.6 out of 10, Exceptional, (90)
"Property was amazing, exactly what is shown in the listing, beds were extremely comfortable, will stay again"
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
A heated pool

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

9.6 out of 10, Exceptional, (81)
"This property is perfectly located near Duval street and within walking distance to the marina. A perfect location for those wanting to shop and enjoy the amenities the marina has to offer. We can’t wait to go back. "
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Harbor Walk Hideaways | Group Compound In Old Town!
Outdoor dining

Harbor Walk Hideaways | Group Compound In Old Town!

10.0 out of 10, Exceptional, (5)
"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "
The price is €916
includes taxes & fees
17 Aug - 18 Aug
Harbor Walk Hideaways | Group Compound In Old Town!
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, (2)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
Interior

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

9.8 out of 10, Exceptional, (139)
"Really like the home and everything was perfect."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
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, (190)
"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!
Waterfront luxury home with private pool
Dining

Waterfront luxury home with private pool

9.8 out of 10, Exceptional, (78)
"We had a wonderful stay at 3/4 time! It is a beautiful VRBO to use in Key West. We truly appreciated all the thoughtful touches that made the place feel like a home away from home.The location was perfect, and the space was clean, comfortable, and well-equipped for a relaxing getaway. We absolueltly loved the heated pool. It was the perfect base for exploring Key West, and we’re already looking forward to our next visit."
Waterfront luxury home with private pool
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Pool

JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL

10.0 out of 10, Exceptional, (108)
"Great place to stay for our spring trip as a family of 3. "
The price is €1,061
includes taxes & fees
3 Sept - 4 Sept
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Tropical Key West out of the way
Pool

Tropical Key West out of the way

9.4 out of 10, Exceptional, (172)
"Thanks for the stay, we loved the pool and peaceful quiet while still being so close to everything. Family dinners on the porch were also a great and relaxing alternative to every meal out. "
Tropical Key West out of the way
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Dining

CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

9.8 out of 10, Exceptional, (136)
"Property was clean and comfortable with everything we needed. Only complaint is the late check in time."
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
TV

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (204)
"Wonderful stay!"
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
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, (87)
"Great location "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated 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!
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, (77)
"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!
Duval Street Suite in Key West
Microwave, dishwasher

Duval Street Suite in Key West

10.0 out of 10, Exceptional, (45)
"Very clean, great location, and would go back"
Duval Street Suite in Key West
Luxury two floor apartment in prime location of famous Duval Street
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (82)
"Perfect place to stay. Great location. "
The price is €639
includes taxes & fees
11 Aug - 12 Aug
Luxury two floor apartment in prime location of famous Duval Street
Oceanview home with private pool & lush landscaping!
A heated pool

Oceanview home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (111)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Oceanview home with private pool & lush landscaping!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

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

9.6 out of 10, Exceptional, (42)
"Very nice retreat on the water. Enjoyed our views from the porch."
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
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 Fleming Key Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Our stay was great the place was very clean also children friendly environment had a lots of games, the staff was great and we had a lot of fun."
Glenroy 2-night trip
Posted 23 hours ago
Blue Flamingo Resort Key West