Fleming Key Rentals
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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 PricingVRBO
- From $395 per night (USD)
Expedia
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)Expedia
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VRBO
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, ...
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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 $105 per night (USD)
VRBO
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 $105 per night (USD)VRBO
- From $568 per night (USD)
Expedia
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 $568 per night (USD)Expedia
- From $1152 per night (USD)
VRBO
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 $1152 per night (USD)VRBO
- From $783 per night (USD)
Expedia
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 $783 per night (USD)Expedia
- From $587 per night (USD)
VRBO
Helen's Hideaway by Brightwild | Oasis with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This corner hideaway is in a prime location just one block from Duval nestled back on Simonton Street. Helen's ...
From $587 per night (USD)VRBO
- From $182 per night (USD)
Expedia
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 $182 per night (USD)Expedia
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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 PricingVRBO
- From $1982 per night (USD)
Expedia
**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 $1982 per night (USD)Expedia
- From $1708 per night (USD)
VRBO
**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 $1708 per night (USD)VRBO
- From $144 per night (USD)
Expedia
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)Expedia
- From $300 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 $300 per night (USD)VRBO
- From $250 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 $250 per night (USD)Expedia
- From $457 per night (USD)
VRBO
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)VRBO
- From $511 per night (USD)
Expedia
Paradise Island 2bed 1bath suite 1block from Duval w\/ shared 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 $511 per night (USD)Expedia
- From $771 per night (USD)
VRBO
3bed 3bath Bimini Suite, 1block from Duval w\/ shared pool, parking, Old Town
- 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 $771 per night (USD)VRBO
- From $478 per night (USD)
Expedia
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 $478 per night (USD)Expedia
- From $770 per night (USD)
VRBO
3bed 2bath Grand Bahama suite w\/ shared pool, 1block from Duval, in Old Town
- 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 $770 per night (USD)VRBO
- From $553 per night (USD)
Expedia
Charming 2bed 2bath suite, 1block from Duval, shared pool, in Old Town
- 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 $553 per night (USD)Expedia
- From $499 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 $499 per night (USD)VRBO
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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 $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 $1154 per night (USD)
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 ...
From $1154 per night (USD)Expedia
- From $375 per night (USD)
VRBO
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 $375 per night (USD)VRBO
- From $342 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 $342 per night (USD)Expedia
- From $274 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 $274 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 $1638 per night (USD)
VRBO
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 $1638 per night (USD)VRBO
- From $203 per night (USD)
Expedia
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 $203 per night (USD)Expedia
- From $339 per night (USD)
VRBO
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 $339 per night (USD)VRBO
- From $216 per night (USD)
Expedia
Curry House Room 1 | Heated Pool & Balcony
- 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 guesth ...
From $216 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Curry House #8 by Brightwild | King Bed, Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $230 per night (USD)VRBO
- From $203 per night (USD)
Expedia
Curry House #7 by Brightwild | King Bed, Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $203 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Curry House #2 by Brightwild | Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $185 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Curry House by Brightwild | Heated Pool - Rm #9
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $211 per night (USD)Expedia
- From $240 per night (USD)
VRBO
Curry House Room 5 | King Bed, 1st Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $240 per night (USD)VRBO
- From $494 per night (USD)
Expedia
Sweet Caroline by Brightwild | Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $494 per night (USD)Expedia
- From $228 per night (USD)
VRBO
Key Lime Cottage by Brightwild | Pool & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $228 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Sugar Pie Suite by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $214 per night (USD)Expedia
- From $190 per night (USD)
VRBO
Honey Bun Hideaway by Brightwild | Pool & Grill!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $190 per night (USD)VRBO
- From $244 per night (USD)
Expedia
Banana Split by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $244 per night (USD)Expedia
- From $209 per night (USD)
VRBO
Creme Brulee Suite by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $209 per night (USD)VRBO
- From $131 per night (USD)
Expedia
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 $131 per night (USD)Expedia
- From $675 per night (USD)
VRBO
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 $675 per night (USD)VRBO
- From $291 per night (USD)
Expedia
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You don’t oft ...
From $291 per night (USD)Expedia
- From $283 per night (USD)
VRBO
African Queen by Brightwild | GREAT Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: African Queen Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seapo ...
From $283 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Pilar's Cottage by Brightwild | Studio w\/Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Pilar Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport distr ...
From $321 per night (USD)Expedia
- From $1255 per night (USD)
VRBO
Harborwalk Hideaways by Brightwild |Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $1255 per night (USD)VRBO
- From $775 per night (USD)
Expedia
Windsor Townhome #4- 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 $775 per night (USD)Expedia
- From $460 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $460 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Anchors Away - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $250 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Red Room at Grand Maloney Hotel with Pool!
- 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 $338 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Margaretaville," your quintessential Key West getaway that offers you the chance to experience life as a loc ...
From $230 per night (USD)Expedia
- From $1563 per night (USD)
VRBO
Captain's Daughter: Oversized home for the whole family w\/private pool & dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1563 per night (USD)VRBO
- From $647 per night (USD)
Expedia
Spacious home with pool & balcony - 1 block from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $647 per night (USD)Expedia
- From $550 per night (USD)
VRBO
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Like many of ...
From $550 per night (USD)VRBO
- From $343 per night (USD)
Expedia
Sky Loft by Brightwild | Penthouse in Prime Spot!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This gem of a top floor apartment is perfect for your weekend getaway. Sky Loft is located just one block away ...
From $343 per night (USD)Expedia
- From $3000 per night (USD)
VRBO
Takeover at the Grand Maloney by Brightwild
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $3000 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
Features.Key West Suites Hotel has an outdoor pool and fitness center
- 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 ...
From $1500 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Banyan Resort - 2 Blocks to Sunset Celebration
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed ...
From $375 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For PricingVRBO
- From $428 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $428 per night (USD)VRBO
- From $125 per night (USD)
Expedia
The Bolivar, Old Town Key West Monthly vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tuck upstairs in the back of a historic Conch house is a home away from home with private back porch. 1 Block walk from ...
From $125 per night (USD)Expedia
- From $485 per night (USD)
VRBO
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $485 per night (USD)VRBO
- From $161 per night (USD)
Expedia
The Patricia, 1 BR, 1 BA monthly vacation rental home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the heart of Old Town Key West is a quaint Key West Home that offers a crisp palette of blue, lime and white ...
From $161 per night (USD)Expedia
- From $668 per night (USD)
VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $668 per night (USD)VRBO
- From $493 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $493 per night (USD)VRBO
- From $549 per night (USD)
VRBO
Two Bedroom Two Bath Balcony Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $549 per night (USD)VRBO
- From $652 per night (USD)
Expedia
Two Bedroom Two Bath Poolside Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $652 per night (USD)Expedia
- From $271 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $271 per night (USD)VRBO
- From $599 per night (USD)
Expedia
1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy one of Old Town's wonderful historic homes with private pool and hot tub. Casa Rosa one of only seventy five remai ...
From $599 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Sunny, Dog-Friendly Historical Home w\/ Private Hot Tub, Central AC, WiFi, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Eloise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $200 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $300 per night (USD)Expedia
- From $383 per night (USD)
VRBO
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa\/Shared Pool, Near Duval St & Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover your perfect oasis at the "Tropical Old Town Bungalow," a charming 2nd-floor unit nestled between the vibrant a ...
From $383 per night (USD)VRBO
- From $617 per night (USD)
Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $617 per night (USD)Expedia
- Click For Pricing
VRBO
Indoor \/ Outdoor Living in Old Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
Click For PricingVRBO
- From $522 per night (USD)
VRBO
Dream Vacation! Near 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 $522 per night (USD)VRBO
- From $154 per night (USD)
VRBO
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Beaches, Dog-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Ella Varela, a beautifully updated Conch Cottage nestled in the heart of Key West, where your furry friend is ...
From $154 per night (USD)VRBO
- From $625 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $625 per night (USD)Expedia
- From $883 per night (USD)
VRBO
The Mesa House by Brightwild | Close to Duval!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $883 per night (USD)VRBO
- From $342 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $342 per night (USD)Expedia
- From $153 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $153 per night (USD)VRBO
- From $157 per night (USD)
Expedia
May 3 ngt. mid-wk..spec.\nclose beach full kitchen & patio\n139.ngt + extras\n\n\n\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $157 per night (USD)Expedia
- From $700 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $700 per night (USD)VRBO
- From $1032 per night (USD)
Expedia
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1032 per night (USD)Expedia
- Click For Pricing
VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For PricingVRBO
- From $892 per night (USD)
Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $892 per night (USD)Expedia
- From $1331 per night (USD)
VRBO
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1331 per night (USD)VRBO
- From $1154 per night (USD)
Expedia
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1154 per night (USD)Expedia
- From $143 per night (USD)
VRBO
Spec. April.19-24\n155.00 night plus extras\nNear beach& Full Kitchen\n& Patio\n\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in the surf. Come soak up the ...
From $143 per night (USD)VRBO
- From $714 per night (USD)
Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $714 per night (USD)Expedia
- From $621 per night (USD)
VRBO
Large 2\/2 Waterfront Condo Great View Pool & Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $621 per night (USD)VRBO
- From $592 per night (USD)
VRBO
Downtown Waterfront 2\/2 Dock & Pool Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $592 per night (USD)VRBO
- From $1452 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1452 per night (USD)VRBO
- From $592 per night (USD)
VRBO
2\/2 Fully Updated Old Town Waterfront Corner Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $592 per night (USD)VRBO
- From $1769 per night (USD)
VRBO
Authentic Key West Adventure! 3 Comfortable Units, 3 Pools, Pets Allowed!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $1769 per night (USD)VRBO
- From $2369 per night (USD)
VRBO
Family and Friends Getaway! 4 Comfortable Units, 3 Pools, Onsite Dining!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $2369 per night (USD)VRBO