search location
Travel Dates:
Reset Dates
786 Rentals In Fleming Key
United States
Florida
Monroe Area
Florida Keys
Key West
Fleming Key
Filters
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
2
2.0
6
Key West Florida Condo
From $491 per night
(USD)
Welcome to the Shady Palms - Private Pool - RealKeyWest
2
3.0
6
Key West Florida Private vacation home
From $311 per night
(USD)
Old Town Getaway
1
1.0
4
Key West Florida Private vacation home
From $155 per night
(USD)
Perfect Location to Key West Action! Garden View, Pool, Bike Rental!
1
1.0
2
Key West Florida Guest house
From $599 per night
(USD)
Wonderful Stay, Amazing Location! 3 Pools, Bar, Pets Allowed!
1
1.0
2
Key West Florida Guest house
From $498 per night
(USD)
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
1
1.0
2
Key West Florida Guest house
From $569 per night
(USD)
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
1
1.0
2
Key West Florida Guest house
From $682 per night
(USD)
Cozy studio cottage in Old Town Key West
1
1.0
4
Key West Florida Cottage
From $200 per night
(USD)
Heart of Key West - 2BR Waterfront at the Galleon Resort
2
2.0
6
Key West Florida Condo
From $709 per night
(USD)
Little Casita: Key West Monthly rental Close to Duval - RealKeyWest
1
1.0
2
Key West Florida Apartment
From $125 per night
(USD)
ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool
5
3.0
12
Key West Florida Private vacation home
From $557 per night
(USD)
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
3
2.0
8
Key West Florida Private vacation home
From $316 per night
(USD)
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
2
2.0
6
Key West Florida Cottage
From $228 per night
(USD)
Tropical Getaway! 3 Pools, Bike Rental, Pets Allowed!
1
1.0
2
Key West Florida Private vacation home
From $499 per night
(USD)
Wonderful Beach Vacation! 3 Pools, Tiki Bar, Bike Rentals, Pets Allowed, Dining!
1
1.0
4
Key West Florida Guest house
From $512 per night
(USD)
Amazing Vacation! 4 Spacious Units! 3 Pools, Tiki Bar, Bike Rental!
4
4.0
8
Key West Florida Guest house
Click For Pricing
Family and Friends Vacation! Pet-friendly!
1
1.0
4
Key West Florida Guest house
From $553 per night
(USD)
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
2
1.0
4
Key West Florida Condo
From $463 per night
(USD)
Sunset views at the Galleon
2
2.0
6
Key West Florida Condo
Click For Pricing
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
4
4.0
8
Key West Florida Condo
From $1335 per night
(USD)
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
3
4.0
6
Key West Florida Private vacation home
From $282 per night
(USD)
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
3
4.0
8
Key West Florida Private vacation home
From $345 per night
(USD)
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
4
3.0
8
Key West Florida Private vacation home
From $313 per night
(USD)
Runaway Bills | 3 Bed, 1 Bath
3
1.0
6
Key West Florida Private vacation home
From $267 per night
(USD)
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
1
1.0
4
Key West Florida Apartment
From $310 per night
(USD)
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
3
3.0
6
Key West Florida Condo
From $699 per night
(USD)
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
4
4.0
8
Key West Florida Condo
From $1232 per night
(USD)
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
4
4.0
8
Key West Florida Condo
From $797 per night
(USD)
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
3
3.0
6
Key West Florida Condo
From $708 per night
(USD)
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
4
3.0
8
Key West Florida Condo
From $1328 per night
(USD)
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
4
5.0
8
Key West Florida Condo
From $868 per night
(USD)
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
3
2.0
6
Key West Florida Condo
From $862 per night
(USD)
Hidden Gem-Key West 3/2 wading pool home with parking -RealKeyWest
3
2.0
6
Key West Florida Private vacation home
From $489 per night
(USD)
coral stone
1
1.0
2
Key West Florida Condo
From $103 per night
(USD)
Seaport Walkabout- the best location in town
2
1.0
6
Key West Florida Private vacation home
From $312 per night
(USD)
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
4
3.0
8
Key West Florida Condo
From $1326 per night
(USD)
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
1
1.0
3
Key West Florida Private vacation home
From $301 per night
(USD)
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
3
3.0
8
Key West Florida Private vacation home
From $250 per night
(USD)
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
4
5.0
8
Key West Florida Private vacation home
From $283 per night
(USD)
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
3
4.0
8
Key West Florida Private vacation home
From $889 per night
(USD)
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
5
5.0
12
Key West Florida Private vacation home
From $1250 per night
(USD)
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
6
7.0
12
Key West Florida Private vacation home
From $345 per night
(USD)
**LA CASITA EN CIMA @ OLD TOWN** Quaint Cottage By Duval + LAST KEY SERVICE...
2
2.0
6
Key West Florida Private vacation home
From $252 per night
(USD)
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
3
2.0
8
Key West Florida Private vacation home
From $210 per night
(USD)
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
4
5.0
10
Key West Florida Private vacation home
From $1237 per night
(USD)
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
6
8.0
16
Key West Florida Private vacation home
From $1701 per night
(USD)
Find Sanity in the Heart of Key West
4
3.0
8
Key West Florida Private vacation home
From $745 per night
(USD)
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
2
3.0
6
Key West Florida Private vacation home
From $742 per night
(USD)
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
5
6.0
12
Key West Florida Private vacation home
From $1404 per night
(USD)
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
4
4.0
8
Key West Florida Private vacation home
From $413 per night
(USD)
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
3
4.0
8
Key West Florida Private vacation home
From $764 per night
(USD)
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
2
2.0
6
Key West Florida Condo
From $631 per night
(USD)
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
1
1.0
4
Key West Florida Condo
From $313 per night
(USD)
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
3
2.0
6
Key West Florida Private vacation home
From $184 per night
(USD)
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
1
1.0
2
Key West Florida Condo
From $179 per night
(USD)
Old Town! Spacious Condo in Historic Home w\/Pool!
1
2.0
4
Key West Florida Condo
From $200 per night
(USD)
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
2
1.0
4
Key West Florida Private vacation home
From $171 per night
(USD)
Dog-friendly home w\/ large private pool only a short walk to Historic Seaport
3
3.0
6
Key West Florida Private vacation home
From $256 per night
(USD)
Little Paradise, Historic Harbor Old Town Key West 2\/2
2
2.0
4
Key West Florida Private vacation home
From $315 per night
(USD)
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
1
1.0
4
Key West Florida Condo
From $108 per night
(USD)
Contemporary Seaside Cottage with a Private Hot Tub & Shared, Heated Pool
1
1.0
4
Key West Florida Condo
From $166 per night
(USD)
Elegant Condo with Entertainment & Private Parking - Great Central Location
1
1.0
4
Key West Florida Condo
From $266 per night
(USD)
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
1
1.0
4
Key West Florida Private vacation home
From $161 per night
(USD)
Dog-friendly condo in prime location - walk to dining & sights, near the beach
2
2.0
6
Key West Florida Condo
From $191 per night
(USD)
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
2
2.0
4
Key West Florida Private vacation home
Click For Pricing
Modern 2BR Condo Old Town\/Balcony & Pool
2
2.0
4
Key West Florida Condo
From $185 per night
(USD)
Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool
1
1.0
4
Key West Florida Condo
From $266 per night
(USD)
7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location
2
2.0
6
Key West Florida Condo
Click For Pricing
Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
1
1.0
4
Key West Florida Condo
From $55 per night
(USD)
Duval Dream Loft by Brightwild | Right on Duval!
2
1.0
8
Key West Florida Apartment
From $505 per night
(USD)
The Collins on Duval by Brightwild
2
1.0
10
Key West Florida Apartment
From $594 per night
(USD)
Old Town home a short walk to Duval\/Couples Oasis
1
2.0
4
Key West Florida Cottage
From $260 per night
(USD)
Relaxing island home\/Great location\/Stylish
1
2.0
4
Key West Florida Cottage
From $230 per night
(USD)
NEW! Completely Renovated \/ Close to Everything
4
2.0
8
Key West Florida Private vacation home
From $368 per night
(USD)
Duval's Duet on Duval by Brightwild
4
2.0
18
Key West Florida Apartment
From $1170 per night
(USD)
The Emelina, Key West Monthly Rental
1
1.0
2
Key West Florida Apartment
From $133 per night
(USD)
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
2
2.0
6
Key West Florida Private vacation home
From $151 per night
(USD)
Conch Cottage by Brightwild | Quiet w\/ Shared Pool
2
1.0
4
Key West Florida Condo
From $155 per night
(USD)
Enjoy Old Town Key West in this Beautifully furnished house
2
2.0
6
Key West Florida Private vacation home
From $600 per night
(USD)
Yellow Room at Grand Maloney by Brightwild
1
1.0
2
Key West Florida Apartment
From $305 per night
(USD)
Blue Room at the Grand Maloney by Brightwild
1
1.0
2
Key West Florida Apartment
From $320 per night
(USD)
Green Room at the Grand Maloney by Brightwild
1
1.0
4
Key West Florida Apartment
From $342 per night
(USD)
Poolside King Room Steps from Duval!
1
1.0
4
Key West Florida Villa
From $379 per night
(USD)
Poolside Queen Room Steps from Duval!
1
1.0
2
Key West Florida Villa
From $299 per night
(USD)
One Bedroom Deck Villa Steps from Duval!
1
1.0
4
Key West Florida Villa
From $446 per night
(USD)
MONTHLY RENTAL, Old Town, Duplex, newly renovated, private backyard
2
2.0
4
Key West Florida Private vacation home
From $200 per night
(USD)
Galleon Resort beach hotel luxury in Old Town Key West
1
1.0
5
Key West Florida Condo
From $495 per night
(USD)
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
3
4.0
8
Key West Florida Private vacation home
From $907 per night
(USD)
Historic Caroline Street Condo!1 Bedroom 2 Bath, Pool, Amazing Old Town Location
1
2.0
2
Key West Florida Condo
From $275 per night
(USD)
A BANANA REPUBLIC in Old Town Key West
2
3.0
6
Key West Florida Private vacation home
From $499 per night
(USD)
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
3
4.0
8
Key West Florida Private vacation home
From $921 per night
(USD)
Contra House by Brightwild | Luxury Home w\/Pool
4
4.0
12
Naval Air Station Key West Florida Private vacation home
From $2252 per night
(USD)
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
3
3.0
8
Key West Florida Private vacation home
From $418 per night
(USD)
Atocha Cottage by Brightwild | Amazing Find!
2
1.0
6
Naval Air Station Key West Florida Apartment
From $536 per night
(USD)
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
4
5.0
10
Key West Florida Private vacation home
From $1129 per night
(USD)
Bananas Foster by Brightwild | Epic Guesthouse!
7
8.0
19
Key West Florida Private vacation home
From $2054 per night
(USD)
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
2
3.0
6
Key West Florida Private vacation home
From $161 per night
(USD)
Updated home with private pool, patio, & grill in enclosed tropical backyard
2
2.0
6
Key West Florida Private vacation home
From $228 per night
(USD)
Hip Studio in Old Town - Walk to the Beach!
1
1.0
2
Key West Florida Apartment
From $190 per night
(USD)
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
1
1.0
4
Key West Florida Hotel resort
Click For Pricing
Load More Results