Fleming Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Fleming Key

Hyatt Vacation Club at Sunset Harbor, Key West
Exterior

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (307)
"We had a nice stay. The property was in a great location."
The price is ￥34,327
￥42,750 total
includes taxes & fees
Sep 4 - Sep 5
Hyatt Vacation Club at Sunset Harbor, Key West
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is ￥9,123
￥34,890 total
includes taxes & fees
Aug 13 - Aug 14
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Exterior

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (393)
"this was exactly as advertised and close to all the action"
The price is ￥13,091
￥32,543 total
includes taxes & fees
Sep 4 - Sep 5
Steps from Duval, Pool on Site & Bikes Included!
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
1 bedroom, free WiFi, bed sheets

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is ￥14,104
￥48,370 total
includes taxes & fees
Aug 7 - Aug 8
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Beach nearby

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (139)
"Confortable b"
The price is ￥14,003
￥36,151 total
includes taxes & fees
Aug 6 - Aug 7
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
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 ￥39,798
￥124,922 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Exterior detail

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (13)
"Great place to stay! Very clean and steps to Duval Ave."
The price is ￥19,309
￥61,445 total
includes taxes & fees
Aug 10 - Aug 11
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Exterior

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (178)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Beach nearby

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (141)
"Very clean, great location and wonderful amenities!"
The price is ￥13,413
￥35,488 total
includes taxes & fees
Aug 6 - Aug 7
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Terrace/patio

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is ￥14,298
￥48,415 total
includes taxes & fees
Aug 27 - Aug 28
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Terrace/patio

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (19)
"Will stay here again "
The price is ￥14,298
￥48,563 total
includes taxes & fees
Aug 10 - Aug 11
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Coconut Mallory Resort And Marina By Kees Vacations
Meeting facility

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations
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!
Resort View 1BR Suite
Apartment

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cleanliness "
The price is ￥33,374
￥50,040 total
includes taxes & fees
Sep 3 - Sep 4
Resort View 1BR Suite
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (295)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Property grounds

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

9.6 out of 10, Exceptional, (161)
"Clean, comfortable and close to everything fun! "
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Beach nearby

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.2 out of 10, Wonderful, (10)
"Great time staying there "
The price is ￥12,929
￥34,876 total
includes taxes & fees
Aug 13 - Aug 14
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
Exterior

Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

10.0 out of 10, Exceptional, (8)
"Great location, friendly and helpful hosts, clean, perfect spot for my solo trip!"
The price is ￥12,971
￥40,930 total
includes taxes & fees
Aug 6 - Aug 7
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!
Beach nearby

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (15)
"We had a great time at this property. The owner is super attentive to detail and immediately responds to any questions or requests. You can really tell that they CARE about their property and guests. Property is well cared for and charming. Highly recommend!"
The price is ￥18,218
￥43,213 total
includes taxes & fees
Aug 17 - Aug 18
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fleming Key Hotel Reviews

Margaritaville Beach House Key West

Margaritaville Beach House Key West

10/10 Excellent
"Great communication with texting option "
Ann 4-night trip
Posted 3 hours ago
Margaritaville Beach House Key West