Fleming Key Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Fleming Key Vacation Homes

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!
Spec @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
Terrace/patio

Spec @125.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 @125.lodg+ Aug & sept. 10 min walk beach, close to all + full kitch& patio
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, (140)
"Really like the home and everything was perfect."
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
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
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!
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 CA $406
CA $992 total
includes taxes & fees
Aug 11 - Aug 12
Luxury two floor apartment in prime location of famous Duval Street
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, (48)
"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!
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
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, (82)
"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!
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Terrace/patio

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

9.8 out of 10, Exceptional, (76)
"Had a great time, easy check in and great location!"
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Terrace/patio

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is CA $354
CA $1,154 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
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!
Oceanfront 4-Bed 3-Bath home with pool
Terrace/patio

Oceanfront 4-Bed 3-Bath home with pool

9.6 out of 10, Exceptional, (74)
"It was a great location in the back, not on the main road. Very quiet, great view, and good place for kids if you are traveling with kids. Used golf carts and was able to get everywhere in 5-10 mins. Overall great vacation and awesome location to stay. "
Oceanfront 4-Bed 3-Bath home with pool
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!!
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
Terrace/patio

Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

9.8 out of 10, Exceptional, (18)
"We had a great time in Key West. The location of this property was great, allowing us to walk pretty much everywhere we wanted to go. The unit was clean and provided all the basics we needed. Will definitely consider staying here again."
The price is CA $190
CA $595 total
includes taxes & fees
Aug 31 - Sep 1
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
Oceanview home with private pool & lush landscaping!
A heated pool

Oceanview home with private pool & lush landscaping!

9.8 out of 10, Exceptional, (113)
"Great place to stay very kid friendly and a short golfcart ride to everything "
Oceanview home with private pool & lush landscaping!
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, (224)
"Such a perfect location! Great stay!"
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Marina

Luxury 3-Bedroom Waterfront Home with Pool AND Dock!

9.8 out of 10, Exceptional, (130)
"Our Key West trip and this property were great. The house had everything we needed and breathtaking views!"
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Kingfish Keep | Lively Escape on Duval! Balcony!
Living area

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (15)
"Awesome location with excellent communication. "
The price is CA $180
CA $526 total
includes taxes & fees
Aug 25 - Aug 26
Kingfish Keep | Lively Escape on Duval! Balcony!
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
Terrace/patio

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

9.2 out of 10, Wonderful, (201)
"Great location, nice accommodations, and easy communication with the host. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT 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 Fleming Key Hotel Reviews

Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

10/10 Excellent
"Staff is personable and efficient, knowledgeable about local activities. The bed was very comfortable. Refrigerator and microwave was a great option for reheating leftovers. The included continental breakfast and free shuttle to town was an awesome convenience feature!"
Terence 5-night trip
Posted 1 day ago
Fairfield Inn and Suites by Marriott Key West