Fleming Key Rentals
- 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
- 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 $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 $136 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 $136 per night (USD)VRBO
- From $133 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 $133 per night (USD)VRBO
- From $244 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 $244 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 $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
- From $183 per night (USD)
VRBO
Secret Casita: Relaxing 2BD\/2BA escape RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO SECRET CASITA! This hidden gem is a wonderful way to embrace the Key West laid-back lifestyle. This first-f ...
From $183 per night (USD)VRBO
- From $224 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 $224 per night (USD)VRBO
- From $1961 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 $1961 per night (USD)VRBO
- From $231 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 $231 per night (USD)VRBO
- From $175 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 $175 per night (USD)VRBO
- Click For Pricing
VRBO
Welcome Aboard! Prime location in Key West on a 46' Luxury Catamaran
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Join us on a 46' luxury sailing catamaran, The Space Between, enjoying all the comforts of home and the added beauty and ...
Click For PricingVRBO
- From $373 per night (USD)
VRBO
Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow. Sleeps 6
- Bedrooms:
- 3
- 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 $373 per night (USD)VRBO
- From $197 per night (USD)
VRBO
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w\/ Pool!
- Bedrooms:
- 3
- 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 $197 per night (USD)VRBO
- Click For Pricing
VRBO
Galleon Key West Resort - Waterfront Marina 2-Bedroom Suite + Beach + Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best view in Key West! Sitting atop the Galleon Resort in a penthouse room with a clear view of the Galleon Marina and h ...
Click For PricingVRBO
- From $330 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 $330 per night (USD)VRBO
- Click For Pricing
Expedia
Price Reduction!!! Penthouse Suite @ KW, Galleon Resort, Avail 6\/29 - 7\/6\/2024
- 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 ...
Click For PricingExpedia
- From $169 per night (USD)
VRBO
Old Town. Spacious 1 bedroom, private heated pool, yard, deck, covered porch.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Old Town. Spacious 1 bedroom on 1st floor. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks ...
From $169 per night (USD)VRBO
- Click For Pricing
Expedia
Osprey- 1 Bed\/1 Bath Nightly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Ideally located at the Colony on Olivia Street. ...
Click For PricingExpedia
- Click For Pricing
VRBO
Charming House - 3 Bedroom 1 Bath with pool.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint property on the edge of Old Town. Minutes walk to White street with cool galleries, yoga studios, restaurants and ...
Click For PricingVRBO
- From $350 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 $350 per night (USD)VRBO
- From $214 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 $214 per night (USD)VRBO
- From $268 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 $268 per night (USD)VRBO
- Click For Pricing
Expedia
Casa Loca- 3 bedroom | 2.5 bath | sleeps up to 8 with private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Loca is perfect for guests who want to enjoy the finest Key West has to offer! The perfect location, less than one ...
Click For PricingExpedia
- From $150 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 $150 per night (USD)VRBO
- From $124 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 $124 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Southard Love - 2.5 Blocks to Downtown, Walk to Beach. 4 Bedrooms, 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 $800 per night (USD)VRBO
- From $300 per night (USD)
VRBO
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 $300 per night (USD)VRBO
- Click For Pricing
Expedia
Hidden Oasis- 1 bedroom 1 bath in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tucked among a colony of freestanding Conch style cottages, amid lush tropical landscaping, sits the newly renovated Hid ...
Click For PricingExpedia
- Click For Pricing
Expedia
Fleming-O 2 bedrooms | 1 bath | sleeps up to 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fleming-O (pronounced “Flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
Click For PricingExpedia
- From $706 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. Thank you for your interest in bookin ...
From $706 per night (USD)VRBO
- From $245 per night (USD)
VRBO
Oasis in Old Town - private heated pool
- Bedrooms:
- 3
- 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 $245 per night (USD)VRBO
- From $461 per night (USD)
VRBO
Pelican Landing Dominica-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $461 per night (USD)VRBO
- From $529 per night (USD)
VRBO
Pelican Landing Falmingo-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $529 per night (USD)VRBO
- From $250 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
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $250 per night (USD)VRBO
- From $363 per night (USD)
VRBO
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 $363 per night (USD)VRBO
- From $500 per night (USD)
VRBO
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...
From $500 per night (USD)VRBO
- From $452 per night (USD)
VRBO
Pelican Landing Bermuda-2bedroom waterfront condo w\/boat slip, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $452 per night (USD)VRBO
- From $536 per night (USD)
VRBO
2 bdrm Condo w\/ boat slip Pelican Landing Bonaire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $536 per night (USD)VRBO
- From $202 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
- Bedrooms:
- 2
- 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 $202 per night (USD)VRBO
- From $528 per night (USD)
VRBO
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 ...
From $528 per night (USD)VRBO
- From $1086 per night (USD)
VRBO
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 $1086 per night (USD)VRBO
- From $541 per night (USD)
VRBO
Key West 44ft Sailboat Wild Thing - spring and summer openings now.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Our business model has changed. We no longer are located at a dock; We are excited to share our moorings at North Flem ...
From $541 per night (USD)VRBO
- From $355 per night (USD)
VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $355 per night (USD)VRBO
- From $290 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 $290 per night (USD)VRBO
- From $344 per night (USD)
VRBO
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
- Bedrooms:
- 5
- 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 $344 per night (USD)VRBO
- From $298 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 $298 per night (USD)VRBO
- From $437 per night (USD)
VRBO
~ 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 $437 per night (USD)VRBO
- From $1587 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 $1587 per night (USD)VRBO
- From $348 per night (USD)
VRBO
~ 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 $348 per night (USD)VRBO
- From $1300 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 $1300 per night (USD)VRBO
- From $363 per night (USD)
VRBO
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 $363 per night (USD)VRBO
- From $908 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 $908 per night (USD)VRBO
- From $704 per night (USD)
VRBO
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 $704 per night (USD)VRBO
- From $242 per night (USD)
VRBO
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 $242 per night (USD)VRBO
- From $140 per night (USD)
VRBO
OLD TOWN\/HISTORIC SEAPORT, large POOL, wrap around porch, 1st floor, Washer\/Drye
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Spacious 1 bedroom. 1st floor in Old Town. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks ...
From $140 per night (USD)VRBO
- From $471 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 $471 per night (USD)VRBO
- From $667 per night (USD)
VRBO
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 $667 per night (USD)VRBO
- From $242 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 $242 per night (USD)VRBO
- From $1334 per night (USD)
VRBO
~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THE PROPERTY: By bringing the outdoors in, this home allows you to live like a true Floridian. The fenced yard provides ...
From $1334 per night (USD)VRBO
- From $253 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 $253 per night (USD)VRBO
- From $957 per night (USD)
VRBO
~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
- Bedrooms:
- 4
- 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 $957 per night (USD)VRBO
- From $412 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 $412 per night (USD)VRBO
- From $942 per night (USD)
VRBO
Hyatt Residence Club, Sunset Harbor - Amazing Resort -Come Enjoy Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical Key West welcomes you to a classic Florida condominium, offering a one bedroom unit with plush queen bed, fully ...
From $942 per night (USD)VRBO
- From $343 per night (USD)
VRBO
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 $343 per night (USD)VRBO
- From $230 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 $230 per night (USD)VRBO
- From $701 per night (USD)
VRBO
~ 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 $701 per night (USD)VRBO
- From $492 per night (USD)
VRBO
~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street with hot tub!
- 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 $492 per night (USD)VRBO
- Click For Pricing
Expedia
Mango Cottage- 2 bedroom 2 bath with private pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in mod ...
Click For PricingExpedia
- From $219 per night (USD)
VRBO
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 $219 per night (USD)VRBO
- From $850 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 $850 per night (USD)VRBO
- From $1528 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 $1528 per night (USD)VRBO
- From $384 per night (USD)
VRBO
PURA VIDA ~ 3 Bed\/3.5 Bath Home on Quaint Old Town Lane!
- Bedrooms:
- 4
- 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 $384 per night (USD)VRBO
- From $403 per night (USD)
VRBO
Miami Vice Sailboat Key West North Fleming Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Our business is growing with new natural setting stay at our moorings in quiet secluded area in Key West Harbor!” We h ...
From $403 per night (USD)VRBO
- From $160 per night (USD)
VRBO
ISLAND PEARL - Cozy Nightly Rental just off Duval RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
WELCOME TO ISLAND PEARL Nestled in the heart of Key West, located behind a main house, the Island Pearl vacation rent ...
From $160 per night (USD)VRBO
- Click For Pricing
Expedia
Casa Margarita- 3 bedrooms | 3 baths | sleeps up to 8 | large heated pool & hot
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Margarita is the perfect luxury retreat if you are looking for a peaceful place that also is in the heart of Old To ...
Click For PricingExpedia
- From $625 per night (USD)
Expedia
Downtown Retreat - A++ Location W\/ Private Heated Pool\/Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $625 per night (USD)Expedia
- From $180 per night (USD)
VRBO
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 $180 per night (USD)VRBO
- From $370 per night (USD)
VRBO
~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
- Bedrooms:
- 3
- 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 $370 per night (USD)VRBO
- From $314 per night (USD)
VRBO
~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 $314 per night (USD)VRBO
- From $651 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 $651 per night (USD)VRBO
- From $293 per night (USD)
VRBO
THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VINTAGE ISLAND PARADISE... Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the mid ...
From $293 per night (USD)VRBO
- From $459 per night (USD)
VRBO
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 $459 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Heavenly Hideaway-Monthly 3BD 2.5BA Private Pool - RealKeyWest
- Bedrooms:
- 2
- 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 $275 per night (USD)VRBO
- From $467 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 $467 per night (USD)VRBO
- Click For Pricing
Expedia
Hidden Treasure- 2 bedroom 2 bath with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find ...
Click For PricingExpedia
- From $167 per night (USD)
VRBO
Feel the Island Winds From Casita In The Clouds: 2 Bed\/2 Bath - Monthly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO CASITA IN THE CLOUD! Your search for the perfect island getaway has ended! This large 3 story, two bedro ...
From $167 per night (USD)VRBO
- From $299 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 $299 per night (USD)VRBO
- Click For Pricing
Expedia
Island Style- 1 bedroom 1 bath in old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Resort-style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amid lu ...
Click For PricingExpedia
- From $170 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 $170 per night (USD)VRBO
- From $445 per night (USD)
VRBO
SERENITY ~ Relax in Ultimate Luxury and Comfort in Old Town Key West!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
LOCAL LIVING.... Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated, 4 bedroom ho ...
From $445 per night (USD)VRBO
- From $374 per night (USD)
VRBO
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 $374 per night (USD)VRBO
- From $857 per night (USD)
VRBO
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 $857 per night (USD)VRBO
- From $1110 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 $1110 per night (USD)VRBO
- From $790 per night (USD)
VRBO
The Galleon Resort in Beautiful Key West. Amazing Views! Over 500 Reviews!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Saturdays only. Overlooking the shimmering span of Gulf of Mexico in histor ...
From $790 per night (USD)VRBO
- From $500 per night (USD)
VRBO
BOTTOMS UP BUNGALOW - 2 Bedroom \/ 2 Bathroom With PRIVATE POOL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West. This pristine Florida Bungalow ...
From $500 per night (USD)VRBO
- From $636 per night (USD)
VRBO
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 $636 per night (USD)VRBO