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Key West Cottage Rentals
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Stay steps from the sand in a Key West Beachfront Cottage designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless Florida Keys getaway.
Vacation Rentals by Owner in Key West Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for places to stay in Key West.
To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website. All bookings are securely completed on our partner websites.
A Touch of Bermuda in Key West
Note: Minimum stay is 29 days / 28 nights. Saturday-to-Saturday bookings required. Exceptions made for special events including boat races and Fantasy Fest. Pets by special permission.
About This Property
A Touch of Bermuda is a privately owned Bermuda-style conch cottage in the Shipyard section of Truman Annex — one of only seven private townhomes available for rent in this gated, 24-hour secured community in the heart of Old Town Key West. This is not a cookie-cutter condo. It .......
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
Down a hidden lane in the heart of Old Town Key West you will find Loco Court. The compound is located one block off Duval St but is completely private and serene.
The compound consists of THREE STAND ALONE COTTAGES alongside a tranquil PRIVATE POOL and connected to each other by a spacious deck.
The first cottage (unit 1) and second cottage (unit 2) each consist of a one bedroom, one bathroom, open kitchen and living room with high ceilings. The third cottage (unit 3) consists of.......
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.
Two of the Queen bedrooms share an en-suite bath easily.......
~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!
THE PROPERTY: This home’s white picket fence and rocking chair front porch beckon you to come inside. Explore the uniqueness of this updated property including its location in Bahama Village, private pool, and pool house.
As you enter your vacation home, enjoy the open concept living room, kitchen, and dining area. In addition, there is a built-in work statio.......
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip in your pool. Whether you lounge in the cabana or enjoy dinner under the stars, this home has it all! Close to the sights and sounds of Duval Street yet quietly surrounded by Bougainvillea and palm trees, you will love this location. The fenced property with private pool has 4 bedrooms and 2.5 baths. It’s perfect for vacationing with friends or kiddos who will enjoy the secon.......
10.0 Star Review
4 Bedrooms
- Sleeps 7
Key West Vacation Rental
Pet Friendly 
Oasis in Old Town - our special home
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our home away from home and we offer it as a MONTHLY rental when we aren’t using it ourselves. It is located in a wonderfully private yet centrally located neighborhood on a hidden lane. as our home away from home. This intimate house boasts many fun and thoughtful features which will help make your stay in Key West special. It has a lovely small freeform heated pool (with a.......
Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-Parking
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and offers a full kitchen, living room, private bedroom, bathroom and sleeper sofa. Private deck just off the master bedroom. Large flat screen tv in living room. Located in the back of the property overlooking a shared common pool area. Large gas grill on property and washer-dryer .Off street parking spot. Enjoy your stay in a true conch home! Note: The property is set up for no co.......
Conch Republic Consul General's Cottage.-Historic District
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval Street. Stay in a traditional Conch Style Home that features Mexican tile floors, spacious master bedroom with queen size bed, guest bedroom with full size bed and one couch sleeper sofa. Two full size bathrooms and inside washer/dryer. Central air conditioning, flat screen tv's and free wifi and open style full kitchen and living room. Pool on property. There is an additional c.......
PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!
RELAXED DOWNTOWN LIVING...
Envelop yourself in true island living in this cute cottage just for the two of you. One of six homes in this exclusive compound located in the heart of Old Town. Located one block from Duval with charming porch and shared heated pool. Walk or stroll to dining, night life, galleries, shopping, and be at fabulous Ft. Zachary beach beach in minutes.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
FURNISHINGS...
Cozy one queen bedroom and one bath. G.......
Sweet Sunshine Garden Flat – Downtown Key West - 2 Blocks Off Duval w Pool Access
Ever dream of vacationing in a sun-kissed Caribbean Cottage-style flat close to the beach, nestled behind a white picket fence in a landscaped tropical garden? Sweet Sunshine Garden Flat can make that dream come true. Set in the beautiful Key West Truman Annex Shipyard condominium complex, flowers and palm trees frame the front entrance like a pretty picture. Pale pink wood-slat siding, a faint-blue front porch ceiling, and a nautical octagon window epitomize Key West nouveau architecture and we.......
Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
WELCOME TO PINEAPPLE COTTAGE!
The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation.
As you enter the cottage, you'll step onto a deck overlooking the backyard, where you'll find the inviting private pool, a charcoal grill, and various seating and lounging areas surrounded by lush tropical landscaping, ensuring you.......
Ann Street Cottage: A bright and airy home near Duval Street
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. Both bathrooms have recently been remodeled and a private laundry is located in the unit.
The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a ple.......
Ann Street Tranquility: A cozy and peaceful cottage
This charming one bedroom cottage is the perfect hideaway.
The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is un.......
Tropical Jewel - Stay Where The Vacation Never Ends- 2BD/2Bath - Private Pool
WELCOME TO TROPICAL JEWEL
Near all the action of the historic seaport and Duval Street, you can get out into the city anytime you want, or quickly retreat back when the party is winding down.
Discover the eclectic charm of this Key West home, just two blocks from the Historic Seaport. This unique property is a perfect blend of colorful, quirky elements that embody the spirit of island living. Relax on the front porch in Adirondack chairs while enjoying a cold beverage.
Conch Cottage - Feels Like Home - 1BD/1Bath - Hot Tub
WELCOME TO CONCH COTTAGE!
In the 20th century many residents of Key West began referring to themselves as “Conchs”, now this term generally applied to all residents of Key West. This vacation home is called Conch Cottage because it encompasses the heart of the Key West life style.
In the heart of Old Town with traditional architecture, this home serves as a perfect luxury and vacation. This home is exactly what you would imagine! From the ginger bread features to the porch .......
Tranquility - Tucked away in The Meadows - Private Pool - 3BD/3Bath
Welcome to Tranquility, a luxurious vacation rental nestled in a tropical setting. This stunning 3 bedroom, 3 bathroom home is the perfect escape for those seeking peace and relaxation.
As soon as you step inside, you'll be struck by the bright and spacious living room that flows into a fully equipped kitchen. French doors open to a deck and private pool, surrounded by palm trees and tropical landscaping for added privacy. Upstairs, you'll find two cozy bedrooms and an additional bathroom.......
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the shared pool. Enjoy being surrounded by the unique quietness in the midst of Old Town. Enter the great room with all the kitchen accoutrements needed to prepare the perfect meal. Dine inside at the kitchen island or outside under the palms. Two spacious bedrooms connect to the private backyard where the hot tub awaits. All 5 star reviews on AIR. Video T.......
Family House, 2 K BR`s, Private Spa/Deck, 2 pools.
The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker`s Cottage from 1880`s. 2 K memory foam beds upstairs w/32” Smart TV`s, Q sleeper sofa (memory foam mattress) in LR with75” Smart TV. Bring your Netflix, Amazon or other UN and PW for your favorite programming. Blue tooth speakers and Alexa`s. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families!
Private rear deck with new 6 person Jacuzzi. 2 heated pools!<.......
10.0 Star Review
2 Bedrooms
- Sleeps 6
Key West Vacation Rental
Pet Friendly
Pete's West Cottage steps from Duval
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room there is a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the p.......
Lennon`s Lodge, Luxury Accommodations for up to 6!
Sophisticated tropical decor with top of the line furniture and amenities. 2 K Tommy Bahama bedrooms, Q sleeper sofa, full kitchen, tumbled marble shower, private rear deck with private 7 person spa and 2 person outdoor shower.
Recently renovated in 2010, spacious 2 K bedroom house that is beautifully decorated. Special attention was paid to keeping the old Cuban floor tile, wherever possible. Your private back yard is perfect for enjoying our wonderful Caribbean days and evenings. Tak.......
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is located just two blocks from world famous Duval Street. Colony Calypso is surrounded by coconut palms and blooming bougainvillea. This charming one bedroom bungalow is a true island hideaway.
The cottage features a one level open concept living and dining area with a full kitchen. The quaint cottage offers a spacious bedroom with a king size bed. The bathroom has a ti.......
Pete's Cottages: Twin Cypress cottages steps from Duval
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each cottage opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room there is a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to th.......
Havana Lane: An updated classic conch cottage with still a rustic edge!
Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio makes you ready to dive right in and relax poolside amongst the tropical foliage. A new expanded Ipe deck area is perfect for an outdoor dinner under the stars or lounge in the oversized sitting area tucked into the landscape. If you follow the path into the back corner of the property you will be rewarded with a beautiful rope loveseat to curl up into, perfect for an afternoon s.......
Pete's East Cottage: Cypress east cottage steps from Duval
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the comfortable living room there is a spiral staircase to the loft second bedroom with unique glass railing. Large windows in the kitchen bi-fold away to allow serving directly to the p.......
Heart of Downtown Key West Cottage With Off-Street Parking
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minutes walk from Duval St. Accommodates 1-2 couples. Your car will be safe in this parking spot, nowhere near the street. The Cottage is set back from the sidewalk so you are not subjected to traffic noises.
Note two things:
1. The price listed is for 2 guests only. There is an additional charge of $75/night for an additional guest.
2. The cottage is set ba.......
A Conch Casita at the Key West Golf Club
This is a unique home in Key West Golf Club Club Community available for your vacation rental experience.
Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort style amenities! The property provides open living areas downstairs and comfortable bedrooms upstairs. The master bedroom has a King bed, ensuite bath with dual vanity and tub/shower combo. There is also a lovely screened balcony to enjoy your evening wine or morning coffee overlooking .......
3 Bedrooms
- Sleeps 6
Key West Vacation Rental
Sunset Suite-2 BR, sleeps 4, King and Queen, Private Spa!
Historic 1880`s Cigar Maker`s cottage completely renovated.
1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV`s, Full kitchen with granite counter tops, new stainless steel appliances.
A newly remodeled bath with tumbled marbled tile shower, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!
K and Q memory foam bedrooms upstairs (32" Smart TV) separated .......
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
Caroline's Cottage KW
Welcome to Caroline’s Cottage steps away from the world’s famous Duval Street in Key West Fla. Your home away from home. We provide the best internet and work desk, so you can bring your work, too. Great neighborhood and not far away from anything on the island.
Caroline’s Cottage KW was rebuilt from the ground up in 2020 keeping the historic and unique shot-gun style of the old Key West conch homes. Caroline’s Cottage is nestled away on a quiet stree.......
Old Town Elegance Island Breezes and Poolside Bliss
Charming Pool Cottage in the Heart of Old Town Key West
Perfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated kitchen and beautifully designed outdoor spaces to enjoy the island breeze.
Property Highlights:
Comfortable Accommodations:
The primary bedroom includes a king bed.......
McCartney`s Manor - Deluxe K Suite W/Pvt. Spa!
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Blue tooth speaker, Alexa Echo, full kitchen w/dishwasher. 65” Smart TV ( bring your PW/UN for Netflix/Amazon or other programming you enjoy). Tumbled marble shower. Part of a gated compound with 3 other units. Beautifully landscaped, lots of orchids, native plants. Next door is the heated shared Family pool at 916 and the Adult heated pool is across the lane.
Built in 2010. Sleeps 2 with Luxury king be.......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Key West Vacation Rental
Pet Friendly
Starr`s Suite - 2 person K Suite w/Private Spa!
Starr`s Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.
Starr`s Suite is in Abbey Road, a gated co.......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Key West Vacation Rental
Pet Friendly
Remodeled cozy retreat - Key West
Kick off your flip flops in this wonderful newly renovated 1 bed,1 bath guest house! After a day at the beach or a late night on Duval, you will love the privacy and cleanliness of Casa Duck.
Private entrance, outdoor shower, fenced-in yard, and patio.
* NEW* Fully stocked Kitchen with Stainless Steel Appliances
* NEW* Full-size closet, with dressing unit
* NEW* Full-size Washer & Dryer
* NEW* Large flat-screen TV
* NEW * Bed/Furniture.......
1 Bedrooms
- Sleeps 2
Key West Vacation Rental
Pet Friendly
Old Town cottage
The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One off-street parking space is provided, not that you really need a car. You are a few blocks from the Old Town attractions. When you enter the front gate you walk onto the front deck where you can grill out and enjoy dinner under the stars and palm leaves or just relax in the hot tub. There is also a rear deck off of the home with couple of chaise lounges chairs great for sunbathin.......
Colony Sunset- Bright and airy cottage in the heart of old town Key West
Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with exposed beams and huge transom windows that extend all the way to the tip of the roof add a bright and airy feeling to the cozy space. Just through the French doors lies a private deck for su.......
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you`re just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property in this downtown island location situated on two full private lots with such lush mature tropical landscaping.
A focal point of this unique property is the Key West quintessential indoor / outdo.......
Corazon - Palm Tree Paradise- Private Pool - 2BD/2.5Bath - Prime Location!
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. With its open floor plan, fully equipped kitchen, and private pool steps from the living area, this is the perfect home for entertaining and relaxation.
Located just one block from the famous Duval Street, Corazon is the ideal spot for experiencing all the excitement and culture that Key West offers. Plus, with the added convenience of the included parking space, you can.......