Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $715 per night (USD)
VRBO
Bermuda Retreat-waterfront 2BR 2BA condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $715 per night (USD)
VRBO
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Expedia
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
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Expedia
From $693 per night (USD)
VRBO
Flamingo Retreat-waterfront 2BR 2BA condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $693 per night (USD)
VRBO
From $322 per night (USD)
VRBO
The Palms -3 bedroom 2 bath home in The Meadows w/ pool oasis & guest cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $322 per night (USD)
VRBO
From $554 per night (USD)
VRBO
Little Paradise, Historic Harbor Old Town Key West 2/1.5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $554 per night (USD)
VRBO
From $952 per night (USD)
VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $952 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Oasis in Old Town - our special home
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $267 per night (USD)
VRBO
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Expedia
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
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Expedia
From $561 per night (USD)
VRBO
Poolside Studio Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting ...
From $561 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $568 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $257 per night (USD)
VRBO
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Expedia
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
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Expedia
From $217 per night (USD)
VRBO
Modern 2BR Condo Old Town/Balcony & Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $217 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Heart of Downtown Key West Cottage With Off-Street Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minut ...
From $486 per night (USD)
Expedia
From $828 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $828 per night (USD)
VRBO
From $879 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $879 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Ocean-breeze Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood f ...
From $160 per night (USD)
VRBO
From $816 per night (USD)
VRBO
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people c ...
From $816 per night (USD)
VRBO
From $188 per night (USD)
VRBO
Cottage in Paradise, Old Town. Walk to Duval & beaches. Hot tub, Pet Friendly.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Our home is in Old Town Key West, within walking distance of Duval Street, White Street art galleries, restaurants, bars ...
From $188 per night (USD)
VRBO
From $325 per night (USD)
VRBO
ShangriLa Suite / Queen Studio / Sleeps 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $325 per night (USD)
VRBO
From $338 per night (USD)
VRBO
LA PUERTA ROSA~Charming 3 bed/2 bath Conch Home in Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $338 per night (USD)
VRBO
From $175 per night (USD)
VRBO
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $175 per night (USD)
VRBO
From $2485 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $2485 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Relaxing island home/Great location/Stylish
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $253 per night (USD)
VRBO
From $190 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town Duplex, private backyard, pets welcome, 2BR/2BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $190 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Yellow Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $504 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Blue Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $540 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Green Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $504 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $271 per night (USD)
VRBO
From $480 per night (USD)
Expedia
Loft Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for where to stay in Key West, Florida? Look no further! Our One Bedroom Loft Villa features a queen bed downsta ...
From $480 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $224 per night (USD)
VRBO
From $370 per night (USD)
Expedia
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $370 per night (USD)
Expedia
From $180 per night (USD)
VRBO
MONTHLY RENTAL, Old Town Duplex, private backyard, 2 BR/2 BA, pets ok
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $180 per night (USD)
VRBO
From $238 per night (USD)
VRBO
WINDSONG DELIGHT - Cute house on Windsor Ln
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This two story townhome has both location and amenities for a wonderful month long visit to Key West. Secluded at the r ...
From $238 per night (USD)
VRBO
From $731 per night (USD)
VRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
From $731 per night (USD)
VRBO
From $619 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $619 per night (USD)
Expedia
From $833 per night (USD)
VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $833 per night (USD)
VRBO
From $353 per night (USD)
Expedia
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambianc ...
From $353 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $450 per night (USD)
VRBO
From $1932 per night (USD)
Expedia
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
Bedrooms:
4
Bathrooms:
8
Sleeps:
20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $1932 per night (USD)
Expedia
From $327 per night (USD)
VRBO
~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $327 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Dreamworks Conch Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PEACEFUL RETREAT... A quintessential Key West cottage in the heart of Old Town and only a few blocks away from Higgs Bea ...
From $205 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion ...
From $432 per night (USD)
VRBO
From $203 per night (USD)
VRBO
Studio overlooking historic Key West waterfront.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathr ...
From $203 per night (USD)
VRBO
From $484 per night (USD)
VRBO
Key West Cottage Located in Old Town Key West. Available March 2025!!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Key West Cottage. Located in the Historic Seaport Area of Old Town. 2 BR. 2 BR. Three HD TV's. Streaming on every TV. W ...
From $484 per night (USD)
VRBO
From $1441 per night (USD)
Expedia
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
Bedrooms:
0
Bathrooms:
2
Sleeps:
4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1441 per night (USD)
Expedia
From $2811 per night (USD)
VRBO
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2811 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street! Experience the best of Key W ...
From $582 per night (USD)
Expedia
From $267 per night (USD)
VRBO
GOOD FEELIN ~ Charming 2 BR/2 Ba Home Conveniently Located w/ Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SPOIL YOURSELF… Come unwind in this tropical retreat allowing for your delightful Key West story to unfold. Sounds of sw ...
From $267 per night (USD)
VRBO
From $223 per night (USD)
Expedia
POSITIVE VIBES ~ Charming 2 BR, 1 Ba Cottage in Peaceful Area w/ Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOST ON ISLAND TIME… Treasure your time together within this charming Key West cottage tucked away on this peaceful and ...
From $223 per night (USD)
Expedia
From $385 per night (USD)
VRBO
GOOD VIBES ~ 2 Cottages w/ 4 BR/3 Ba, Outdoor Oasis and Parking!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
MEMORIES TO LAST A LIFETIME… This unique set of 2 charming, Conch style homes provide the perfect compound setting for y ...
From $385 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w/private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $310 per night (USD)
Expedia
From $1411 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1411 per night (USD)
VRBO
From $3258 per night (USD)
Expedia
1 Block to Duval St | Banana's Foster Guesthouse
Bedrooms:
7
Bathrooms:
7
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $3258 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $445 per night (USD)
VRBO
From $134 per night (USD)
VRBO
Conch Republic Studio - Key West Millionaires Row
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
In the center of Key West's prestigious "Millionaires Row," Conch Republic Studio is a tranquil getaway for one or a cou ...
From $134 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Galleon Resort Efficiency in the old town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size b ...
From $349 per night (USD)
VRBO
From $390 per night (USD)
Expedia
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $390 per night (USD)
Expedia
From $804 per night (USD)
VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $804 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
VRBO
From $408 per night (USD)
Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $408 per night (USD)
Expedia
From $916 per night (USD)
VRBO
★2BR Resort Villa at Heart of Old Town Key West- Sleeps 6!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $916 per night (USD)
VRBO
Click For Pricing
Expedia
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
Click For Pricing
Expedia
From $675 per night (USD)
VRBO
Hyatt Sunset Harbor, 2BD overlooking the stunning and beautiful Gulf of Mexico!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $675 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Quiet Conch House in Historic District
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $256 per night (USD)
Expedia
Click For Pricing
VRBO
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For Pricing
VRBO
From $1810 per night (USD)
Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1810 per night (USD)
Expedia
From $883 per night (USD)
VRBO
SEAPORT SERENITY-Beach-Pool-King-BBQ-Hot Tub-Extra Entrance
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND ...
From $883 per night (USD)
VRBO
From $1544 per night (USD)
Expedia
Epic location, Private Parking - Commodore's Cove
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of a home. Up to 12 can st ...
From $1544 per night (USD)
Expedia
From $3124 per night (USD)
VRBO
Epic Location Near Duval, Private Hot Tub, Parking
Bedrooms:
7
Bathrooms:
8
Sleeps:
24
Summary: Welcome to Commodore's Compound, an incredible 8 bed, 7 bath home in prime location situated just one short blo ...
From $3124 per night (USD)
VRBO
From $1589 per night (USD)
Expedia
Steps from Duval, Private Hot Tub - Seaport Suite
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Located in the heart of Old Town Key West, Seaport Suite is the ideal getaway for large groups of up to 12 gues ...
From $1589 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Paradise on Eaton- 3 bedroom 3 bath home w/private pool near Historic Seaport
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $392 per night (USD)
VRBO
From $266 per night (USD)
VRBO
Our Key West Dream in Seaport.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Family home for over 20 years, we would like to share our home to those that want to relax, see an amazing sunset, and e ...
From $266 per night (USD)
VRBO
From $557 per night (USD)
VRBO
BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
OLD TOWN PARADISE.... Paradise awaits in a quiet Old Town location. This four bedroom home is set on a cozy lane that i ...
From $557 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Ohana Paradise At The Historic Seaport , Old Town. Private Home.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amaz ...
From $399 per night (USD)
VRBO
From $1751 per night (USD)
VRBO
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1751 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $445 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $326 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Colony Sunset- Bright and airy cottage in the heart of old town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing ...
From $535 per night (USD)
VRBO
From $652 per night (USD)
VRBO
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $652 per night (USD)
VRBO
From $800 per night (USD)
Expedia
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $800 per night (USD)
Expedia
From $973 per night (USD)
VRBO
Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $973 per night (USD)
VRBO
From $926 per night (USD)
Expedia
Washer & Dryer, Near Downtown - Mesa House, Dos
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Whether you're lounging on the front porch or enjoying a seafood dinner inside, this 2-Bedroom Suite at The Mes ...
From $926 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Washer & Dryer, Near Downtown - Mesa House, Uno
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Mesa House, Uno, is a charming condo in a prime location with a large front porch. Great for couples on a weeke ...
From $485 per night (USD)
VRBO
From $949 per night (USD)
Expedia
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $949 per night (USD)
Expedia
From $771 per night (USD)
VRBO
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $771 per night (USD)
VRBO
From $212 per night (USD)
VRBO
Conch Republic House - Key West Millionaires Row
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In the center of Key West's prestigious "Millionaires Row," Conch Republic House is a tranquil getaway for up to six in ...
From $212 per night (USD)
VRBO
From $405 per night (USD)
VRBO
little bodega in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Very nice 1 br/bath house on Solaris Hill centered 2 blks off Duvall St. in Old Town Key West. Enjoy bustling Duvall wi ...
From $405 per night (USD)
VRBO
From $930 per night (USD)
Expedia
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN IN THE ...
From $930 per night (USD)
Expedia
From $783 per night (USD)
VRBO
Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to La Margarita, a newly renovated home with coastal charm only blocks away from Duval Street, the Historic Seap ...
From $783 per night (USD)
VRBO
From $2032 per night (USD)
Expedia
Tropical Tranquility - 4BR Luxury Villa In Old Town Key West w Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town ...
From $2032 per night (USD)
Expedia
From $1772 per night (USD)
VRBO
Key West Suites Hotel # 205
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
From $1772 per night (USD)
VRBO
From $1751 per night (USD)
Expedia
Key West Suites Hotel #201 on Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1751 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Charming Old Town Bungalow
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Charming two story, 3 Bedroom 3 Bathroom. Renovated home built in 1908, on a corner lot in Historical Old Town Key West. ...
From $465 per night (USD)
VRBO
From $1731 per night (USD)
Expedia
Secret Villa I @ Old Town with Private Pool, close to Duval!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1731 per night (USD)
Expedia
From $1107 per night (USD)
VRBO
SERENDIPITY ~ Grand 4 Bedroom/4.5 Bathroom Home in Heart of Key West!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
TIME TO CREATE LIFELONG MEMORIES… Your long-awaited island retreat is sure to have all expectations exceeded within this ...
From $1107 per night (USD)
VRBO
From $1522 per night (USD)
Expedia
3-Story spacious conch style home w/ private pool & dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1522 per night (USD)
Expedia

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Results: 763 Rentals