Key West National Wildlife Refuge Rentals
From $1343 per night (USD)VRBO
Spacious Oceanfront Stay! Spa, Fitness, & Steps to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1343 per night (USD)VRBO
From $476 per night (USD)VRBO
Chic Stay Near Newport Harbor & Cliff Walk! Pool, Spa, Fitness Center!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $476 per night (USD)VRBO
From $696 per night (USD)VRBO
Spacious Lanai Suite! Pool, Marina Access, Walk to Dining Spots & Museums
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $696 per night (USD)VRBO
From $1042 per night (USD)VRBO
Stylish Suite w/ Oceanfront View, Pool, Spa, & Steps to Historic Newport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1042 per night (USD)VRBO
From $942 per night (USD)VRBO
Pet-Friendly Ocean View Stay! Pool, Spa, Historic Sights Nearby!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $942 per night (USD)VRBO
From $1168 per night (USD)VRBO
Lux Gulf View Suite! Pool, Marina Access, Walk to Dining Spots & Museums!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1168 per night (USD)VRBO
From $162 per night (USD)VRBO
Shipwreck Suite - Apartment on Duval St, Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Stay like a true Key West local in this one-of-a-kind Duval St apartment! Here you'll wake up in the heart of downtown - ...
From $162 per night (USD)VRBO
From $1038 per night (USD)Expedia
4th of July in Key West at the Hyatt Vacation Club at Sunset Harbor - 2BR Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the beauty of Key West from this amazing 2-bedroom resort. The bedrooms feature a king bed and a queen bed, ens ...
From $1038 per night (USD)Expedia
Click For PricingVRBO
Magnificent views of the Gulf, Sunset Harbor is the ultimate island retreat.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Key West, this delightful resort offers 2 bedrooms with a king and queen bed, 2 bathrooms with luxurious amen ...
Click For PricingVRBO
From $396 per night (USD)Expedia
Pet Friendly / Hot Tub / Close to Everything
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Historic Old Town Monthly Rental La Cala is Situated on a Corner Lot within Walking Distance to Everything yo ...
From $396 per night (USD)Expedia
From $557 per night (USD)VRBO
Hyatt Sunset Harbor. Oct 19 to 26. Fantasy Fest. Studio unit. 7 night rental.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical Key West welcomes you to a classic Florida studio villa offering a plush king bed, casual living area with TV ...
From $557 per night (USD)VRBO
From $1690 per night (USD)VRBO
Perfect for Families! 2BR Suite with Balconies, Onsite Pool, Private Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1690 per night (USD)VRBO
From $1690 per night (USD)VRBO
Sea Breeze 2 Bedroom Oceanfront Suite at The Pier House Resort & Spa
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1690 per night (USD)VRBO
From $1875 per night (USD)VRBO
Pet-friendly Accommodation with Balcony, Outdoor Pool, Private White Sand Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1875 per night (USD)VRBO
From $1864 per night (USD)VRBO
Havana Heights Two Bedroom Suite at The Pier House Resort & Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1864 per night (USD)VRBO
From $1350 per night (USD)Expedia
Premier resort overlooking the Gulf. Walk to Mallory Square, restaurants, beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the wester ...
From $1350 per night (USD)Expedia
From $472 per night (USD)VRBO
Hyatt Sunset Harbor 1-bedroom suite w/AC, WiFi, Pool, Walk to Duval & Mallory
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience Key West in this enchanting 1-bedroom sleep4 suite with kitchen, living area with a queen sofa bed. Perfect f ...
From $472 per night (USD)VRBO
From $444 per night (USD)Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 2, Swimming Pool, Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
From $444 per night (USD)Expedia
From $463 per night (USD)VRBO
Southern Escape at Truman Annex - 2 Bed / 2.5 Bath with Parking & Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME to Southern Escape! Located in the Truman Annex Foundry building. This newly remodeled 2-bedroom, 2.5-bathroo ...
From $463 per night (USD)VRBO
From $176 per night (USD)Expedia
Tropical Cottage - Entire house in the center of Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This delightful retreat is a free standing newly renovated cottage with lovely private deck, front porch, and a dedicate ...
From $176 per night (USD)Expedia
From $379 per night (USD)VRBO
Banana Wind at Truman Annex - 2 Bed / 2.5-Bath Condo w/ Shared Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME to Banana Wind! Located in the Truman annex Foundry building. Discover the beauty of Key West from this marve ...
From $379 per night (USD)VRBO
From $849 per night (USD)Expedia
Sailfish Suite on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Sailfish Suite, your tropical retreat located in the heart of Key West! Situated on lively Duval Street, ...
From $849 per night (USD)Expedia
From $557 per night (USD)VRBO
Waterfront Resort, RWO Championship Boat Races, Old Town, Swimming Pool, Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Have I mentioned that this listing is for the Race World Offshore Championship Boat Races in sunny Key West, FL? You wil ...
From $557 per night (USD)VRBO
From $248 per night (USD)Expedia
Charming studio in Key West -Close to Duval. Beautiful Pool area.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical Key West welcomes you to a classic Florida studio condominium, offering a plush king-size bed, casual living ar ...
From $248 per night (USD)Expedia
From $197 per night (USD)VRBO
Check out Hemmingway's 1st residence in the heart of downtown Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Want to live in paradise on a beautiful island for a month? Check out Hemmingway's 1st residence in the heart of downtow ...
From $197 per night (USD)VRBO
From $169 per night (USD)VRBO
Apartment in the heart of downtown Key West 1 block off Duval with private pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Want to live in paradise for a month? A one-bedroom large apartment downtown in the heart of Key West, one block off Duv ...
From $169 per night (USD)VRBO
From $141 per night (USD)VRBO
Apartment in historical hotel/home downtown Key West, one block off Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A beautiful loft style apartment in a historical hotel/home in the heart of Key West awaits you! There is an 8ft deep pr ...
From $141 per night (USD)VRBO
From $471 per night (USD)VRBO
Coral Palms Spacious 1BR Condo, King, Queen, Sofa Bed, Pool, Block to Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed with r ...
From $471 per night (USD)VRBO
From $601 per night (USD)VRBO
Charming Island Home w/ Pool & Guest Quarters in the Heart of Downtown Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the vibrant heart of Key West, this exquisite island home offers a perfect blend of tropical charm and modern ...
From $601 per night (USD)VRBO
From $912 per night (USD)VRBO
Fantastic Location, Old Town Waterfront Galleon Resort+Amenities, 2-Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 !! Our Galleon Resort accommodations in Historic Old Town-Key West, Florida – Where ...
From $912 per night (USD)VRBO
From $1680 per night (USD)VRBO
2 Sunset Harbor Resort, Marina, In Town, Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in an upscale place that’s near everything you want to visit. This stylish place is close to must-see destinations ...
From $1680 per night (USD)VRBO
From $1790 per night (USD)VRBO
2 Hyatt Sunset Harbor Resort, In Town, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This stylish place is close to must-see destinations. Discover this relaxing oasis in the heart of Key West's famed Old ...
From $1790 per night (USD)VRBO
From $462 per night (USD)VRBO
PARADISE ON PORTER in the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise on Porter is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West. Th ...
From $462 per night (USD)VRBO
From $3804 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the glamour of this stylish, upscale place. Overlooking the shimmering span of Gulf of Mexico in historic Old Tow ...
From $3804 per night (USD)VRBO
From $872 per night (USD)VRBO
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $872 per night (USD)VRBO
From $506 per night (USD)Expedia
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $506 per night (USD)Expedia
From $288 per night (USD)VRBO
30% Discount Summer Sale Aug Sept 2025 /Villa /close to everything/off st prking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
READ ADDITIONAL REVIEWS -Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Any discounts offered ...
From $288 per night (USD)VRBO
From $724 per night (USD)Expedia
Private Island Oasis Getaway, A Dream Vacation
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Imagine the ultimate Key West dream home that feels like a faraway oasis - a short ferry ride to Sunset Key will have yo ...
From $724 per night (USD)Expedia
From $268 per night (USD)VRBO
A SALTWATER REMEDY ~ 2 BR/2.5 Ba Townhome Truman Annex w/ Shared Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PERFECT CAREFREE RETREAT... Located in the small private community of Porter Court within Truman Annex and set around a ...
From $268 per night (USD)VRBO
From $345 per night (USD)Expedia
SUMMER SAVINGS!!!! \nLatitude Adjustment @ Truman Annex Shipyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Latitude Adjustment located in the Truman Annex Shipyard just steps from beaches, restaurants & bars, Key We ...
From $345 per night (USD)Expedia
From $924 per night (USD)VRBO
Tropical Oasis in the Truman Annex with a private pool\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Searching for the perfect vacation home away from it all? Your hunt ends in here! A Wave from it All is a recently remod ...
From $924 per night (USD)VRBO
From $242 per night (USD)Expedia
THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
CUTE CONDO IN STEPS FROM IT ALL… This 2 bedroom, 1 bath ground level flat is located in The Shipyard, a neighborhood of ...
From $242 per night (USD)Expedia
Click For PricingVRBO
Sunset Harbor Beach Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hyatt Sunset Harbor Resort is located in Key West, 2,300 feet from Mallory Square. Key West Aquarium is 2,650 feet from ...
Click For PricingVRBO
From $641 per night (USD)VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $641 per night (USD)VRBO
From $1584 per night (USD)VRBO
Luxury 4BDR/4BA Penthouse | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Luxury Harbor House Suites! We proudly offer you a newly renovated 2,400SF, 4BDR/4BA Penthouse in the Cit ...
From $1584 per night (USD)VRBO
From $1915 per night (USD)Expedia
Harbor House Suite A | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $1915 per night (USD)Expedia
From $677 per night (USD)VRBO
World's End at Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy spectacular 3-way Key West views from the large wrap-around deck without leaving your rental unit. This 2 bedroom ...
From $677 per night (USD)VRBO
From $438 per night (USD)VRBO
Ann Street Tranquility: A cozy and peaceful cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $438 per night (USD)VRBO
From $288 per night (USD)VRBO
Classic King & Private Balcony - Curry Mansion Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $288 per night (USD)VRBO
From $1738 per night (USD)Expedia
Key West Suites Hotel #201 on Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1738 per night (USD)Expedia
Click For PricingVRBO
“LOCATION”
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic Location. Only minutes from Duval St. Quaint 2 bd/ba with lots of space and a great kitchen. Short walk to mar ...
Click For PricingVRBO
From $373 per night (USD)Expedia
PAPA'S CASITA in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Even Hemingway would have loved this place! Amazing renovation from top to bottom of this mid 1800's historic home locat ...
From $373 per night (USD)Expedia
From $4402 per night (USD)VRBO
Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests
- Bedrooms:
- 5
- Bathrooms:
- 11
- Sleeps:
- 20
This private four (4) house compound accommodates (20) guests and is has a private 10′ x 25′ heated pool including a 5’ ...
From $4402 per night (USD)VRBO
From $394 per night (USD)Expedia
Unlock your Paradise Adventure - Between Sloppy Joe's and the Harbor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 story Townhouse is in "Old Town Villas". A Caribbean inspired community in the heart of Key West. Built in 2017. ...
From $394 per night (USD)Expedia
From $360 per night (USD)VRBO
Snowbird-friendly condo with private balcony, garden views, W/D, on-site pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Happy Hour Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $360 per night (USD)VRBO
From $334 per night (USD)Expedia
Two Bed One Bath Ground Floor End Unit in the Heart of Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
TRUMAN ANNEX: The Rooster Retreat is a lovely two bedroom, one bathroom ground floor end unit with a spacious backyard d ...
From $334 per night (USD)Expedia
From $797 per night (USD)VRBO
**SALTWATER SAPPHIRE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A highlight o ...
From $797 per night (USD)VRBO
From $270 per night (USD)Expedia
Dog-friendly house + guesthouse with private hot tub - less than a mile to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Tropic Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $270 per night (USD)Expedia
From $523 per night (USD)VRBO
FunSeeker 1/2 block off Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Only one block to the Hemingway House and two blocks to the Green Parrot bar! Restaurants, beaches, bars, entertainment ...
From $523 per night (USD)VRBO
From $619 per night (USD)Expedia
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine waking up every morning in Paradise. With Balconies that overlook the marina and ocean. Private marina, private ...
From $619 per night (USD)Expedia
From $2828 per night (USD)VRBO
CLASSIC KEY WEST - Grand home in Old Town location
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedroo ...
From $2828 per night (USD)VRBO
From $1188 per night (USD)VRBO
PERFECTION...STEPS FROM DUVAL ~
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everyth ...
From $1188 per night (USD)VRBO
From $3586 per night (USD)VRBO
WATSON HOUSE GRAND ESTATE on Simonton St
- Bedrooms:
- 11
- Bathrooms:
- 11
- Sleeps:
- 22
The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gather ...
From $3586 per night (USD)VRBO
From $694 per night (USD)Expedia
Near Duval: Hot Tub, Sleeps 6, Top Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bed ...
From $694 per night (USD)Expedia
From $1077 per night (USD)VRBO
Just steps to Duval- Sleeps 10- Pool House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, ...
From $1077 per night (USD)VRBO
From $1867 per night (USD)Expedia
Steps to Duval-Pool-Hot tub- Sleeps 16- BIG groups
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Perfect for bachelor and bachelorette parties, these 2 cottages that are quintessential Key West. Some of those ...
From $1867 per night (USD)Expedia
From $400 per night (USD)VRBO
Truman Annex 2 bedroom 2.5 bath Townhouse- steps from Duval Street with pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Full renovation completed in August 2024. This beautiful townhouse has a perfect location in Truman Annex. Truman Annex ...
From $400 per night (USD)VRBO
From $1318 per night (USD)Expedia
**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval & Beach + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BAHAMIAN BAMB ...
From $1318 per night (USD)Expedia
From $409 per night (USD)VRBO
A BLUE BEAUTY at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stunning, Modern 2 bedroom, 1 bathroom ground floor condo in the Truman Annex Shipyard Complex completely renovated. Fu ...
From $409 per night (USD)VRBO
From $219 per night (USD)Expedia
Private Home in Heart of Old Town (Shared Pool!)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $219 per night (USD)Expedia
From $875 per night (USD)VRBO
SEAPORT SKYLINE-Beach-Pool-King-BBQ-Hot Tub-Rooftop views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. PENTHOUSE COND ...
From $875 per night (USD)VRBO
From $222 per night (USD)Expedia
Caroline On My Mind-New Listing-Light, Bright and Airy!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $222 per night (USD)Expedia
From $1031 per night (USD)VRBO
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This prope ...
From $1031 per night (USD)VRBO
From $490 per night (USD)Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $490 per night (USD)Expedia
From $344 per night (USD)VRBO
SUMMER RATES STARTING AT 200 PER NIGHT!!! \nMAI TAI TERRACE - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Mai Tai Terrace located in The Shipyard subdivision of Truman Annex in beautiful Key West. This 2-bedroom, ...
From $344 per night (USD)VRBO
From $674 per night (USD)VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- 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 $674 per night (USD)VRBO
From $294 per night (USD)VRBO
Blue Bayou: Ideal Key West Location W/ Shared Pool, Steps from Beach, Duval Street & Mallory Square!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, with no exceptions. Please review additiona ...
From $294 per night (USD)VRBO
From $319 per night (USD)Expedia
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latitudes Restaurant!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, and no exceptions can be made. Please revie ...
From $319 per night (USD)Expedia
From $439 per night (USD)VRBO
Historic house near Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This private home is located on a secluded lane just behind the Key West Lighthouse across from the Hemingway Home Museu ...
From $439 per night (USD)VRBO
From $1468 per night (USD)Expedia
**ELEGANT ESCAPE @ THE ANNEX** Lavish Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! There’s no be ...
From $1468 per night (USD)Expedia
From $900 per night (USD)VRBO
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $900 per night (USD)VRBO
From $335 per night (USD)Expedia
Lavender Jungle by AvantStay | Great Location w/ Patio & Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $335 per night (USD)Expedia
From $589 per night (USD)VRBO
Truman's Hideaway by AvantStay | Great Location w/ Patio, Outdoor Dining & BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $589 per night (USD)VRBO
From $325 per night (USD)Expedia
Conch Adventure by AvantStay | Great Location w/ Patio, Outdoor Dining
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $325 per night (USD)Expedia
From $521 per night (USD)VRBO
Sundown Refuge by AvantStay | Great Location w/ Outdoor Dining & Shared Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $521 per night (USD)VRBO
From $437 per night (USD)Expedia
Linger Longer by AvantStay | Key West Walkable | Gated Community, Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $437 per night (USD)Expedia
From $201 per night (USD)VRBO
La Casita by AvantStay | Steps to Duval Street | Month Long Stays Only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* The location of La Casita cannot be beaten -- right ...
From $201 per night (USD)VRBO
From $404 per night (USD)Expedia
Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $404 per night (USD)Expedia
From $168 per night (USD)VRBO
Emma's Secret by AvantStay | Heart of Old Town | Month Long Stays Only
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Located in one of Key West’s historic and most cult ...
From $168 per night (USD)VRBO
From $938 per night (USD)Expedia
Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Week Long Stays Only
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $938 per night (USD)Expedia
From $465 per night (USD)VRBO
Parrot Perch by AvantStay | Old Town Key West w/ Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $465 per night (USD)VRBO
From $473 per night (USD)Expedia
Artist Garden by AvantStay | Great Location w/ Balcony, Shared Pool & BBQ!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $473 per night (USD)Expedia
From $524 per night (USD)VRBO
Key West Found by AvantStay | Close to Shops w/ Patio & Shared Pool! |
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $524 per night (USD)VRBO
From $525 per night (USD)Expedia
Bahamian Reed by AvantStay | Walk to Everything! w/ Community Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $525 per night (USD)Expedia
From $241 per night (USD)VRBO
Serenity by AvantStay | Guest House in Old Town w/ Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*Please note that this home is available for 28+ night stays only.* Located in Bahama Village, a quaint neighborhood in ...
From $241 per night (USD)VRBO
From $450 per night (USD)Expedia
Shipyard Treasure by AvantStay | Communal Pool, Gated Community | Great Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $450 per night (USD)Expedia
From $340 per night (USD)VRBO
Always Your Paradise by AvantStay | Shared Pool | Near Zachary Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $340 per night (USD)VRBO
From $669 per night (USD)Expedia
Key West Casa by AvantStay | Communal Pool | BBQ & Patio | Near Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $669 per night (USD)Expedia
From $443 per night (USD)VRBO
Breezy Bungalow by AvantStay | Close 2 Zachary Taylor State Park & Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $443 per night (USD)VRBO
From $434 per night (USD)Expedia
Southard Getaway by AvantStay | w/ Covered Patio, Great Location & Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $434 per night (USD)Expedia