Fleming Key Rentals
From $1186 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 $1186 per night (USD)VRBO
From $294 per night (USD)Expedia
Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Dade County pine house has a strong connection to the sea. It was built in 1910 by ship's carpenters and owned for ...
From $294 per night (USD)Expedia
From $1181 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 $1181 per night (USD)VRBO
From $561 per night (USD)Expedia
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 $561 per night (USD)Expedia
From $1441 per night (USD)VRBO
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)VRBO
From $355 per night (USD)Expedia
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 $355 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 $1738 per night (USD)Expedia
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 $1738 per night (USD)Expedia
From $226 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 $226 per night (USD)VRBO
From $346 per night (USD)Expedia
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 $346 per night (USD)Expedia
From $241 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $241 per night (USD)VRBO
From $279 per night (USD)Expedia
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 $279 per night (USD)Expedia
From $263 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 $263 per night (USD)VRBO
From $904 per night (USD)Expedia
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 $904 per night (USD)Expedia
From $323 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 $323 per night (USD)VRBO
From $872 per night (USD)Expedia
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 $872 per night (USD)Expedia
From $727 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 $727 per night (USD)VRBO
From $708 per night (USD)Expedia
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 $708 per night (USD)Expedia
From $890 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 $890 per night (USD)VRBO
From $109 per night (USD)Expedia
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 $109 per night (USD)Expedia
From $223 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 $223 per night (USD)VRBO
From $740 per night (USD)Expedia
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $740 per night (USD)Expedia
From $289 per night (USD)VRBO
OLD TOWN SUMMER’24! Private pool, stunning decor, 5-star reviews. NO PETS
- Bedrooms:
- 1
- 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 $289 per night (USD)VRBO
From $197 per night (USD)Expedia
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 $197 per night (USD)Expedia
From $185 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 $185 per night (USD)VRBO
From $315 per night (USD)Expedia
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 $315 per night (USD)Expedia
From $258 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 $258 per night (USD)VRBO
From $268 per night (USD)Expedia
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 $268 per night (USD)Expedia
From $174 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 $174 per night (USD)VRBO
From $731 per night (USD)Expedia
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)Expedia
From $514 per night (USD)VRBO
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 $514 per night (USD)VRBO
From $338 per night (USD)Expedia
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 $338 per night (USD)Expedia
From $2015 per night (USD)VRBO
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 $2015 per night (USD)VRBO
From $309 per night (USD)Expedia
~ 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 $309 per night (USD)Expedia
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 $431 per night (USD)Expedia
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 $431 per night (USD)Expedia
From $302 per night (USD)VRBO
Historic, Cozy, prime location with amazing pool and garden in Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a little piece of Key West Paradise? Well, this is it! This stunning cottage is only steps away from the His ...
From $302 per night (USD)VRBO
From $136 per night (USD)Expedia
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 $136 per night (USD)Expedia
From $468 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 $468 per night (USD)VRBO
From $368 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 $368 per night (USD)Expedia
From $765 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 $765 per night (USD)VRBO
From $262 per night (USD)Expedia
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 $262 per night (USD)Expedia
From $554 per night (USD)VRBO
Dominica 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 $554 per night (USD)VRBO
From $520 per night (USD)Expedia
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 $520 per night (USD)Expedia
From $294 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 $294 per night (USD)VRBO
From $438 per night (USD)Expedia
Sunny condo with pool, lovely deck, central AC & washer/dryer - central location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Oceana Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $438 per night (USD)Expedia
From $457 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 $457 per night (USD)VRBO
From $185 per night (USD)Expedia
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $185 per night (USD)Expedia
Click For PricingVRBO
Centrally located home with private pool & furnished patio - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Passover Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For PricingVRBO
From $339 per night (USD)Expedia
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $339 per night (USD)Expedia
From $338 per night (USD)VRBO
Quaint, Quiet & Convenient - CasaBianca is The Perfect Old Town Sanctuary
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to CasaBianca! Here you'll find the character & charm of Old Town blended perfectly with all the modern amenitie ...
From $338 per night (USD)VRBO
From $1303 per night (USD)Expedia
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio mak ...
From $1303 per night (USD)Expedia
From $376 per night (USD)VRBO
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into indi ...
From $376 per night (USD)VRBO
From $477 per night (USD)Expedia
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $477 per night (USD)Expedia
From $355 per night (USD)VRBO
~ SOLARIS GARDEN ~ Relax and enjoy this Bohemian dream on a quaint lane.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: Bohemian bits indoors and lush landscaping outdoors will give you that tropical island feeling you are loo ...
From $355 per night (USD)VRBO
From $638 per night (USD)Expedia
~ CASABLANCA ~ Fabulous home w/ private pool/parking, in a quiet location.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Between the welcoming front porch and the private pool, you will be sure to enjoy fresh air and sunshine d ...
From $638 per night (USD)Expedia
From $1386 per night (USD)VRBO
~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. ...
From $1386 per night (USD)VRBO
From $324 per night (USD)Expedia
~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key Wes ...
From $324 per night (USD)Expedia
From $1188 per night (USD)VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...
From $1188 per night (USD)VRBO
From $519 per night (USD)Expedia
Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Boats are located at the Perry Marina! Summer special starting 6/1/25 until 10/1/25 receive upon weather availability-a ...
From $519 per night (USD)Expedia
From $1677 per night (USD)VRBO
~QUEEN CONCH ~ Amazing location with pool and room for family and friends!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
THE PROPERTY: Enjoy your stay in the tropics at the highly touted "Queen Conch" complex, which includes 3 separate renta ...
From $1677 per night (USD)VRBO
From $281 per night (USD)Expedia
ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...
From $281 per night (USD)Expedia
From $465 per night (USD)VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $465 per night (USD)VRBO
From $666 per night (USD)Expedia
Hyatt Sunset Harbour Resort-Prime location on Key West!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All rentals will be in seven-night increments with a Friday through Sunday for check-in. Thank you for choosing Dash R ...
From $666 per night (USD)Expedia
From $316 per night (USD)VRBO
WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
STUNNING KEY WEST RETREAT… Just renovated, this island gem exudes the utmost island spirit with authentic historic chara ...
From $316 per night (USD)VRBO
From $852 per night (USD)Expedia
~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** Chavez House is available for 28 night minimum for the month of August ONLY. Live like a local! THE PROPERTY: By br ...
From $852 per night (USD)Expedia
From $341 per night (USD)VRBO
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Ke ...
From $341 per night (USD)VRBO
From $958 per night (USD)Expedia
~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THE PROPERTY: Nancy & Carl invite you to share their love of the island in their enchanted 3-bedroom home. Live like a l ...
From $958 per night (USD)Expedia
From $435 per night (USD)VRBO
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentio ...
From $435 per night (USD)VRBO
From $429 per night (USD)Expedia
LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
MARITIME-INSPIRED LIVING… Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw ...
From $429 per night (USD)Expedia
From $297 per night (USD)VRBO
The Hollinsed House \"Victorian Delights\" - Large 1 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $297 per night (USD)VRBO
From $774 per night (USD)Expedia
~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are ...
From $774 per night (USD)Expedia
From $516 per night (USD)VRBO
~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished duplex home comes with Key West charm and c ...
From $516 per night (USD)VRBO
From $298 per night (USD)Expedia
Hollinsed House Poolside / King 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 $298 per night (USD)Expedia
From $636 per night (USD)VRBO
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $636 per night (USD)VRBO
From $366 per night (USD)Expedia
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $366 per night (USD)Expedia
From $864 per night (USD)VRBO
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $864 per night (USD)VRBO
From $802 per night (USD)Expedia
Historic \"Old Town\" Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
* We are activally cleaning and sanitizing this rental with extra sanitation methods with each stay. LUXURY IN OLD TOWN ...
From $802 per night (USD)Expedia
From $620 per night (USD)VRBO
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $620 per night (USD)VRBO
From $208 per night (USD)Expedia
Just Restored One Bedroom Hideaway with Garden and Hot Tub 5 No Need For A Car
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has eve ...
From $208 per night (USD)Expedia
From $306 per night (USD)VRBO
~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $306 per night (USD)VRBO
From $378 per night (USD)Expedia
~ROOSTER CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Rooster Conch, part of the highly touted "Queen Conch" complex, which in ...
From $378 per night (USD)Expedia
From $747 per night (USD)VRBO
SEA CONCH~ Amazing location with shared pool, deck, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Enjoy your stay in the tropics at Sea Conch, part of the highly touted "Queen Conch" complex, which includ ...
From $747 per night (USD)VRBO
From $242 per night (USD)Expedia
Heavenly Hideaway-Monthly 3BD 2.5BA Private Pool - RealKeyWest
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 6
HEAVENLY HIDEAWAY! Welcome to our Heavenly Hideaway, a serene oasis nestled in the heart of Key West. This enchanting 3 ...
From $242 per night (USD)Expedia
From $354 per night (USD)VRBO
THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
VINTAGE ISLAND PARADISE... Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the mid ...
From $354 per night (USD)VRBO
From $451 per night (USD)Expedia
PURA VIDA ~ 3 Bed/3.5 Bath Home on Quaint Old Town Lane!
- Bedrooms:
- 3
- 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 $451 per night (USD)Expedia
From $613 per night (USD)VRBO
Miami Vice Sailboat Used For TV Series with 2 Hour Sandbar Motor Boat Trip
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
*Our business is now in a pristine marina at the stock island division in Key West. Perry Marina has a shuttle that ru ...
From $613 per night (USD)VRBO
From $447 per night (USD)Expedia
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get wit ...
From $447 per night (USD)Expedia
From $259 per night (USD)VRBO
TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR/3BA - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Tranquility, a luxurious vacation rental nestled in a tropical setting. This stunning 3 bedroom, 3 bathroom h ...
From $259 per night (USD)VRBO
From $415 per night (USD)Expedia
CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO CONCH COTTAGE! In the 20th century many residents of Key West began referring to themselves as “Conchs”, no ...
From $415 per night (USD)Expedia
From $435 per night (USD)VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $435 per night (USD)VRBO
From $1738 per night (USD)Expedia
Key West Suites Hotel - Adam Scott Rote Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...
From $1738 per night (USD)Expedia
From $1097 per night (USD)VRBO
Rare Penthouse 2 bed/2bath additional King in loft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $1097 per night (USD)VRBO
From $889 per night (USD)Expedia
The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...
From $889 per night (USD)Expedia
From $757 per night (USD)VRBO
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West. A true guest favorite with over 1 ...
From $757 per night (USD)VRBO
From $641 per night (USD)Expedia
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $641 per night (USD)Expedia
From $1186 per night (USD)VRBO
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...
From $1186 per night (USD)VRBO
From $386 per night (USD)Expedia
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 $386 per night (USD)Expedia
From $465 per night (USD)VRBO
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 $465 per night (USD)VRBO
From $362 per night (USD)Expedia
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 $362 per night (USD)Expedia