Fleming Key Rentals
- From $183 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 $183 per night (USD)VRBO
- From $335 per night (USD)
VRBO
Key West Cottage Located in Old Town Key West
- 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 $335 per night (USD)VRBO
- Click For Pricing
VRBO
2BR Condo - Galleon Resort & Marina - Walk to Mallory Square and Duval Street
- 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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Island Song - Paradise in the Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Song is a 2-Bedroom, 2-Bath Paradise! Centrally located on Key West, this condo has the best backyard in town, t ...
Click For PricingVRBO
- From $436 per night (USD)
VRBO
Atocha Cottage by Brightwild | Amazing Find!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Atocha is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport district of ...
From $436 per night (USD)VRBO
- From $1260 per night (USD)
VRBO
NEW LISTING Old Town Private Pool in Garden Of Eden tropical spa-like Oasis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
( NEW LISTING SEE VRBO LISTING 1223004 for reviews on my other property ) Newly renovated, invitingly spacious, serenely ...
From $1260 per night (USD)VRBO
- From $1980 per night (USD)
VRBO
Contra House by Brightwild | Luxury Home w\/Pool
- 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 $1980 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $425 per night (USD)Expedia
- From $2000 per night (USD)
VRBO
The Admiral of the Seaport
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
The Admiral of the Seaport is a luxurious custom built estate located in the heart of Old Town Key West. Just 3 blocks ...
From $2000 per night (USD)VRBO
- From $299 per night (USD)
VRBO
OLD TOWN SUMMER’24! Private pool, stunning decor, 5-star reviews. NO PETS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sun yourself on the back patio, then cool off in the pool. Rinse off in the outdoor shower with hot/cold running water. ...
From $299 per night (USD)VRBO
- Click For Pricing
VRBO
BEAUTIFUL NEW MONTHLY RENTAL - Old Town Key West - top of the line furnishings
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Old Town Villas is a Caribbean inspired community of only 20 units in the heart of Key West This luxurious townhome is l ...
Click For PricingVRBO
- From $474 per night (USD)
VRBO
Knot A Worry Monthly Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Knot A Worry is a monthly vacation home in the heart of Old Town Key West! Just one block from famous Duval Street wher ...
From $474 per night (USD)VRBO
- From $241 per night (USD)
VRBO
Conch Easy Livin` Monthly Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Discover Conch Easy LIvin' at this monthly vacation home in the heart of Old Town Key West! You'll get a real feel of th ...
From $241 per night (USD)VRBO
- From $130 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 $130 per night (USD)VRBO
- From $140 per night (USD)
VRBO
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 $140 per night (USD)VRBO
- From $241 per night (USD)
VRBO
GOOD VIBES ~ 2 Cottages w\/ 4 BR\/3 Ba w\/ 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 $241 per night (USD)VRBO
- From $846 per night (USD)
VRBO
Windsor Townhome #6- 3 bedroom 3.5 bath with private pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
From $846 per night (USD)VRBO
- From $280 per night (USD)
Expedia
Downtown Conch House-Historic Old Town 3 bedroom, 3 bath home w\/private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $280 per night (USD)Expedia
- From $499 per night (USD)
VRBO
★Family Friendly 2BR Condo 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 $499 per night (USD)VRBO
- From $1062 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1062 per night (USD)Expedia
- From $2230 per night (USD)
VRBO
Bananas Foster by Brightwild | Epic Guesthouse!
- Bedrooms:
- 8
- 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 $2230 per night (USD)VRBO
- From $162 per night (USD)
Expedia
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $162 per night (USD)Expedia
- From $618 per night (USD)
VRBO
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Completed in 1992, this two bedroom two bath home was designed by a local architect for the relaxed Key West tropical li ...
From $618 per night (USD)VRBO
- From $300 per night (USD)
Expedia
HONU WAVE - 2 Bedroom \/ 2 Bathroom - Old Town Key West W\/ Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come relax in Key West at Honu Wave, located in Old Town Key West just 4 blocks from Duval Street and 6 blocks to the be ...
From $300 per night (USD)Expedia
- From $228 per night (USD)
VRBO
Updated home with private pool, patio, & grill in enclosed tropical backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $228 per night (USD)VRBO
- Click For Pricing
VRBO
THE GALLEON - UNIT B-42
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort, Unit B-42. Available Saturday Nov 9, 2019 thru Saturday Nov 16, 2019 (7 nights) . Sleeps six. Pool a ...
Click For PricingVRBO
- From $195 per night (USD)
VRBO
Hip Studio in Old Town - Walk to the Beach!
- 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 $195 per night (USD)VRBO
- From $150 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 $150 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Galleon Resort Efficiency in the old town
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $225 per night (USD)VRBO
- Click For Pricing
Expedia
Galleon Resort available. 2\/19\/21-2\/26\/21
- 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, ...
Click For PricingExpedia
- From $562 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 $562 per night (USD)VRBO
- Click For Pricing
VRBO
Galleon Resort 2bed\/2bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bed/2bath overlooking Marina. King master bedroom. Queen in 2nd bedroom. Sleeper sofa in living room. Jacuzzi tub in m ...
Click For PricingVRBO
- Click For Pricing
VRBO
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 PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $395 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4
- 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 $395 per night (USD)VRBO
- Click For Pricing
VRBO
The Galleon Resort Nov 2 - Nov 9, 2019\/ Boat Week 2019 Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great unit for boat week in Key West. Saturday to Saturday availability. 2 bedroom condo at The Galleon Resort sleeps 6 ...
Click For PricingVRBO
- From $766 per night (USD)
VRBO
★Family Friendly 2BR Condo 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 $766 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 PricingExpedia
- From $639 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the stunning and beautiful Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Fridays, Saturdays and Sundays only. Discover a relaxing oasis overlooking ...
From $639 per night (USD)VRBO
- Click For Pricing
VRBO
Studio unit at the Galleon Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon offers studio type units that can sleep two to four people depending on the unit. All units are air conditio ...
Click For PricingVRBO
- From $133 per night (USD)
VRBO
Conch House in the Historic District
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $133 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $1711 per night (USD)
VRBO
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1711 per night (USD)VRBO
- From $300 per night (USD)
VRBO
2-Story Waterfront Condo near Old Town + Pool and Boat Slip, Available Monthly
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Bay Villas is a charming 2-story waterfront condo located on Hilton Haven Road, a quiet cul-de-sac on Trumbo Point, whic ...
From $300 per night (USD)VRBO
- From $895 per night (USD)
VRBO
SEAPORT SERENITY at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- 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 $895 per night (USD)VRBO
- From $179 per night (USD)
Expedia
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $179 per night (USD)Expedia
- From $519 per night (USD)
VRBO
Commodore's Cove by Brightwild | Private Hot Tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $519 per night (USD)VRBO
- From $1103 per night (USD)
Expedia
Commodore's Compound by Brightwild | HUGE Home!
- 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 $1103 per night (USD)Expedia
- From $714 per night (USD)
VRBO
Seaport Suite by Brightwild | 2nd Story Hideaway!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Situated in the heart of Old Town Key West, Seaport Suite is the perfect vacation spot for large groups of up t ...
From $714 per night (USD)VRBO
- From $670 per night (USD)
Expedia
Helen's Hideaway | Heated Pool & Prime Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Helen's Hideaway is a true Key West oasis! Nestled away off of Simonton St, this 3 bed 3 bath home sits just 1 ...
From $670 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Paradise on Eaton- 3 bedroom 3 bath home w\/private pool near Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $241 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Our Key West Dream in Seaport.
- Bedrooms:
- 3
- 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 $261 per night (USD)VRBO
- From $787 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 $787 per night (USD)VRBO
- Click For Pricing
VRBO
Galleon Resort - Balcony Overlooking Marina w\/ Stair to Boardwalk, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WATERFRONT TWO BEDROOMS, 2 BATHS, FULL KITCHEN IN KEY WEST HISTORIC SEAPORT Condo type unit with an area of 1300 squar ...
Click For PricingVRBO
- From $274 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 $274 per night (USD)VRBO
- From $1679 per night (USD)
Expedia
**GRAND KEY OASIS @ THE ANNEX** Magnificent Estate & Large Pool + LAST KEY SERVI
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The vacation ...
From $1679 per night (USD)Expedia
- From $144 per night (USD)
VRBO
The Estela, Old Town Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away just 1 block from the action of Duval Street lies our newest space located at 613 Fleming Street. Find your ...
From $144 per night (USD)VRBO
- From $227 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $227 per night (USD)VRBO
- From $270 per night (USD)
VRBO
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 $270 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
- 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 $254 per night (USD)Expedia
- From $306 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 $306 per night (USD)VRBO
- From $457 per night (USD)
Expedia
ABSOLUTE KEY WEST in Truman Annex
- Bedrooms:
- 3
- 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 $457 per night (USD)Expedia
- From $454 per night (USD)
VRBO
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $454 per night (USD)VRBO
- From $740 per night (USD)
Expedia
Bimini suite-3 bedroom 3 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $740 per night (USD)Expedia
- From $467 per night (USD)
VRBO
Mesa House, Dos by Brightwild | Unreal Location
- 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 $467 per night (USD)VRBO
- From $269 per night (USD)
Expedia
Mesa House, Uno by Brightwild | Perfect Location
- 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 $269 per night (USD)Expedia
- From $703 per night (USD)
VRBO
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $703 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w\/pool, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please note that all guests MUST be 25 years of age or older. This policy ensures a peaceful and enjoyable experience fo ...
From $460 per night (USD)Expedia
- From $153 per night (USD)
VRBO
Conch Republic House - Key West Millionaires Row
- Bedrooms:
- 3
- 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 $153 per night (USD)VRBO
- From $341 per night (USD)
Expedia
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 $341 per night (USD)Expedia
- From $285 per night (USD)
VRBO
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! MODERN IN THE ...
From $285 per night (USD)VRBO
- From $675 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 $675 per night (USD)VRBO
- From $553 per night (USD)
VRBO
Great Location & Amenities! Pool & Garden View, Pets Allowed, Onsite Dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $553 per night (USD)VRBO
- From $645 per night (USD)
VRBO
Adventure Awaits! Partial Harbor View, Onsite Dining, 2 Blocks Away From Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $645 per night (USD)VRBO
- From $398 per night (USD)
VRBO
Dream Vacation! Near The Famous Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $398 per night (USD)VRBO
- Click For Pricing
VRBO
Amazing Vacation for 16 Guests! 3 Pools, Onsite Dining Pets Allowed!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $1061 per night (USD)
VRBO
Tropical~Tranquility
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Extraordinarily secluded and completely hidden from view on a sleepy artist’s lane is a special slice of Key West you wo ...
From $1061 per night (USD)VRBO
- From $1500 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 $1500 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $399 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $560 per night (USD)
VRBO
Exquisite Elegance in Old Town Key West: Your Stylish Sanctuary Awaits
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This stylish Conch home is tucked away on a quiet lane in Old Town Key West. Newly remodeled, impressively decorated 3 B ...
From $560 per night (USD)VRBO
- From $1063 per night (USD)
VRBO
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 $1063 per night (USD)VRBO
- From $441 per night (USD)
VRBO
SERENDIPITY ~ Grand 4 Bedroom\/4.5 Bathroom Home in Heart of Key West!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
TIME TO CREATE LIFELONG MEMORIES… Your long-awaited island retreat is sure to have all expectations exceeded within this ...
From $441 per night (USD)VRBO
- Click For Pricing
Expedia
Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!
- Bedrooms:
- 4
- 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 ...
Click For PricingExpedia
- From $300 per night (USD)
VRBO
\"Island Time\" in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Island Time" located in the heart of Old Town! This 2nd floor condo is perfect home base for your adventure ...
From $300 per night (USD)VRBO
- From $377 per night (USD)
Expedia
2 Blocks east of Sloppy Joes on QUIET Peacon Lane. Kids and Pets welcome.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Single family home. Not a condo. We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. P ...
From $377 per night (USD)Expedia
- Click For Pricing
VRBO
Walk to Duval St and Mallory Square - 2BR Condo at Heart of Old Town Key West
- 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 ...
Click For PricingVRBO
- From $285 per night (USD)
Expedia
Carriage House at Grand Maloney by Brightwild
- 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 $285 per night (USD)Expedia
- From $244 per night (USD)
VRBO
Bunk Room at the Grand Maloney by Brightwild
- 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 $244 per night (USD)VRBO
- From $168 per night (USD)
Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $168 per night (USD)Expedia
- From $336 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $336 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Solimar Key West - private pool and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Solimar" - Spanish for sun and ocean! Located in the heart of historic Old Town Key West, just blocks from D ...
From $300 per night (USD)Expedia
- From $114 per night (USD)
VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $114 per night (USD)VRBO
- From $495 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $495 per night (USD)Expedia
- From $1664 per night (USD)
VRBO
~ VILLA JOSINE ~ 4 B\/4.5 BA large designer home with pool in a great location
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This arc ...
From $1664 per night (USD)VRBO
- From $1065 per night (USD)
VRBO
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1065 per night (USD)VRBO
- From $330 per night (USD)
VRBO
Bright and Comfortable 3 bedroom\/2.5 bath Classic Conch in the Meadows
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This Dade County pine house has a strong connection to the sea. It was built in the early 1900's by ship's carpenters an ...
From $330 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
The Curry House by Brightwild | Historic Guesthome
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $1500 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Curry House #6 by Brightwild | King Bed, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guest ...
From $195 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Curry House by Brightwild | Balcony & Pool -Rm 3&4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $323 per night (USD)Expedia