Key West Rentals
- From $1453 per night (USD)
VRBO
Amazing Land and Sea Getaway! Four Convenient Rooms, Close to Nearest Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1453 per night (USD)VRBO
- From $1278 per night (USD)
VRBO
Ideal Location for Family and Friends! Four Spacious Rooms, Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1278 per night (USD)VRBO
- Click For Pricing
VRBO
Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart of Old Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Casa Sol, your charming retreat in the heart of Old Town Key West! This delightful Conch House offers you the ...
Click For PricingVRBO
- From $383 per night (USD)
Expedia
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa\/Shared Pool, Near Duval St & Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover your perfect oasis at the "Tropical Old Town Bungalow," a charming 2nd-floor unit nestled between the vibrant a ...
From $383 per night (USD)Expedia
- From $476 per night (USD)
VRBO
FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO FOUNDRY 7! Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find ...
From $476 per night (USD)VRBO
- From $342 per night (USD)
VRBO
THE QUARTERDECK ~ Colorful & Comfortable 2Ba\/ 1Ba Unit in The Shipyard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of ...
From $342 per night (USD)VRBO
- From $582 per night (USD)
VRBO
GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
WHEN ONLY THE BEST WILL DO... Located in the Casa Marina Area of Key West known for spacious and elegant fine homes; the ...
From $582 per night (USD)VRBO
- From $702 per night (USD)
VRBO
JASMINE PLACE:1 block to Duval - Private Pool - Parking! - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO JASMINE PLACE! Jasmine Place is a beautiful and enchanting home conveniently located next door to the Ernes ...
From $702 per night (USD)VRBO
- From $355 per night (USD)
VRBO
Classic Key West living w\/ a full kitchen, balcony, & shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $355 per night (USD)VRBO
- From $205 per night (USD)
Expedia
~Reel Paradise~Beautiful private townhouse in a small gated community.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $205 per night (USD)Expedia
- From $630 per night (USD)
VRBO
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $630 per night (USD)VRBO
- From $272 per night (USD)
VRBO
Looking for Relaxing Location for Your Next Getaway? Premium Ocean View Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $272 per night (USD)VRBO
- From $329 per night (USD)
VRBO
BOOMERANG BOATHOUSE ~ Relax in This Beautiful 4 Bedroom\/2.5 Bath Location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows. T ...
From $329 per night (USD)VRBO
- From $517 per night (USD)
Expedia
LATITUDE 24 ~ 3 B\/3 Ba Two-Story Home in Old Town with Lush Outdoor Oasis!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
ARRIVE IN PARADISE... Step into island time with this incredibly bright and inviting Key West home in a beautiful and qu ...
From $517 per night (USD)Expedia
- From $852 per night (USD)
VRBO
MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated pool, and close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
LOCATION LOCATION LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or b ...
From $852 per night (USD)VRBO
- From $978 per night (USD)
VRBO
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West. Located on Southard Street just steps from Du ...
From $978 per night (USD)VRBO
- From $805 per night (USD)
VRBO
CONCH HEAVEN ~ Stylish 2B\/2Ba, Sleeps 6 in Old Town w\/ Heated Cocktail Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OLD TOWN LOCATION... A beautifully furnished and comfortable home, located just 5 short blocks to Duval Street. Have bi ...
From $805 per night (USD)VRBO
- From $945 per night (USD)
VRBO
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms. Open the rear French doors to a p ...
From $945 per night (USD)VRBO
- From $289 per night (USD)
VRBO
SEA LA VIE ~ Living in Complete Luxury in This Elegant Three Story Home!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town. This home is elegant, yet quite the tropical del ...
From $289 per night (USD)VRBO
- From $238 per night (USD)
VRBO
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $238 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Stone's Throw ~ Beautiful home in a great location with shared pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLOSE TO THE FUN.... This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer! Liter ...
From $175 per night (USD)VRBO
- From $1056 per night (USD)
VRBO
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1056 per night (USD)VRBO
- From $1102 per night (USD)
VRBO
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $1102 per night (USD)VRBO
- From $878 per night (USD)
VRBO
STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $878 per night (USD)VRBO
- From $1952 per night (USD)
VRBO
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $1952 per night (USD)VRBO
- From $869 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Home in Desirable Downtown Location!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $869 per night (USD)VRBO
- From $418 per night (USD)
VRBO
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $418 per night (USD)VRBO
- From $186 per night (USD)
VRBO
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
IMMACULATE RETREAT JUST STEPS FROM IT ALL... Beautifully designed and decorated townhouse located in the Southernmost Ca ...
From $186 per night (USD)VRBO
- From $929 per night (USD)
VRBO
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $929 per night (USD)VRBO
- From $593 per night (USD)
VRBO
ATLANTIC BREEZE ~ 2B\/2BA Renovated Retreat w\/ Pool, Fitness Area & Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACHES ON BOTH SIDES... This newly renovated two bedroom condo is close to the airport, beaches, restaurants and minute ...
From $593 per night (USD)VRBO
- From $154 per night (USD)
VRBO
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Beaches, Dog-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Ella Varela, a beautifully updated Conch Cottage nestled in the heart of Key West, where your furry friend is ...
From $154 per night (USD)VRBO
- From $193 per night (USD)
VRBO
HEMINGWAY'S HIDEOUT ~ Sophisticated, Historic Old Town Cottage with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ISLAND SOPHISTICATION AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms ...
From $193 per night (USD)VRBO
- From $250 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Point ...
From $250 per night (USD)VRBO
- From $393 per night (USD)
VRBO
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ADORING RETREAT ONE BLOCK FROM DUVAL… One bedroom gem on Simonton Street one block from Duval. Totaling one bedroom, on ...
From $393 per night (USD)VRBO
- Click For Pricing
VRBO
Hyatt Windward Pointe 2 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
★Excellent Key West Location - Oceanside Property - 2-Bedroom - 2-Bathroom - Sleeps 6. ★Very Clean - Very Nice Property ...
Click For PricingVRBO
- Click For Pricing
Expedia
Luxurious Keywest resort condominium unit on the Atlantic.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax in style at the Hyatt Windward Pointe Resort. Located on the Atlantic Ocean. Enjoy beautiful sunrises from your ow ...
Click For PricingExpedia
- From $287 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $287 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Gulf Getaway by Brightwild | Condo w\/Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $202 per night (USD)Expedia
- From $645 per night (USD)
VRBO
The Most Perfect Old Town Key West Location for a Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroo ...
From $645 per night (USD)VRBO
- From $915 per night (USD)
VRBO
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
YOUR OCEANFRONT OASIS AWAITS... This remarkable and magical retreat is sure to provide all the R & R you need to refresh ...
From $915 per night (USD)VRBO
- From $358 per night (USD)
VRBO
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
- 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 $358 per night (USD)VRBO
- From $625 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $625 per night (USD)Expedia
- From $927 per night (USD)
VRBO
The Mesa House by Brightwild | Close to Duval!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $927 per night (USD)VRBO
- From $324 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $324 per night (USD)Expedia
- From $191 per night (USD)
VRBO
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $191 per night (USD)VRBO
- From $214 per night (USD)
VRBO
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $214 per night (USD)VRBO
- From $271 per night (USD)
VRBO
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
PICTURE PERFECT PARADISE... This newly renovated 3 bedroom, 2 bathroom retreat is nestled in the highly sought-after, hi ...
From $271 per night (USD)VRBO
- From $350 per night (USD)
VRBO
A Bit of Heaven- Monthly Rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Bit of Heaven This quintessential Key West eyebrow home is located in Old Town's prime Historic District sitting just ...
From $350 per night (USD)VRBO
- From $509 per night (USD)
VRBO
Bahama Breeze- Monthly Rental
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This newer 3 bedroom 3.5 bath home in Old Town is a rare find. There is off street parking and a beautiful private pool ...
From $509 per night (USD)VRBO
- From $107 per night (USD)
VRBO
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $107 per night (USD)VRBO
- From $606 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $606 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Elegantly Furnished Key West Condo in the Truman Annex.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. The condo ...
From $550 per night (USD)Expedia
- Click For Pricing
VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For PricingVRBO
- From $519 per night (USD)
Expedia
Cloud Suite on Duval | Luxury Condo, Epic Location
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of w ...
From $519 per night (USD)Expedia
- From $305 per night (USD)
VRBO
GARDEN HIDEAWAY ~ Beautiful lush landscaped oasis located in the Casa Marina!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
PARADISE AWAITS... This charming home is located in one of the most desirable locations in Key West, Casa Marina. Garden ...
From $305 per night (USD)VRBO
- From $211 per night (USD)
Expedia
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location, Location, LOCATION!!! Perfectly located in Old Town Key West, this beautifully remodeled 3 bedroom, 2 bathroom ...
From $211 per night (USD)Expedia
- From $320 per night (USD)
VRBO
A PEACE OF PARADISE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $320 per night (USD)VRBO
- From $898 per night (USD)
Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $898 per night (USD)Expedia
- From $248 per night (USD)
VRBO
Key Lime Cottage (Monthly)
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Located on the edge of Old Town near the art district on White Street the Key Lime Cottage offers great accommodations f ...
From $248 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Esperanza Suite- Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Esperanza Suite is a bi-level suite with a very spacious upstairs King bedroom with a writing desk and chair and a color ...
From $237 per night (USD)VRBO
- From $399 per night (USD)
VRBO
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $399 per night (USD)VRBO
- From $152 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $152 per night (USD)Expedia
- From $625 per night (USD)
VRBO
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Best rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sunday ...
From $625 per night (USD)VRBO
- From $243 per night (USD)
VRBO
SMATHER'S BEACH, Deluxe 2 BR oceanview unit, GREAT RATES ,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront at Smathers Beach in beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private o ...
From $243 per night (USD)VRBO
- From $1450 per night (USD)
VRBO
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $1450 per night (USD)VRBO
- From $552 per night (USD)
VRBO
Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
'The Plantation' is a NO SMOKING or VAPING,3 bed 3 bath townhome located within the gated community of Truman Annex in K ...
From $552 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $198 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Roosters Perch at Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $299 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Atlantic Ocean view across from Smathers Beach - La Brisa - Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open floor plan, 2 bedroom, 2 bath condo at La Brisa. Gated condo community. Large deep pool with saunas in the pool b ...
From $250 per night (USD)VRBO
- Click For Pricing
Expedia
Thalia`s Retreat at Duval Square- 2 bedroom 2.5 bath with shared rooftop pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
Click For PricingExpedia
- From $399 per night (USD)
VRBO
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s ri ...
From $399 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Beachfront, Deluxe 3 BR oceanfront condo, great rates
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Oceanfront at Smathers Beach in Beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private oa ...
From $371 per night (USD)VRBO
- Click For Pricing
Expedia
Orchid Suite- 1 bedroom 1.5 bath with shared pool one half block off Duval
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with ...
Click For PricingExpedia
- From $600 per night (USD)
VRBO
\"Tranquility \" At Ann Street Gardens Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $600 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $565 per night (USD)VRBO
- Click For Pricing
Expedia
Windsor Townhome #3 - Green Gecko
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
Click For PricingExpedia
- From $148 per night (USD)
VRBO
May 3 ngt. mid-wk..spec.\nclose beach full kitchen & patio\n139.ngt + extras\n\n\n\n\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $148 per night (USD)VRBO
- Click For Pricing
Expedia
Porchside Paradise - 1 bedroom 1 bath just steps away from Duval street.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
Click For PricingExpedia
- From $643 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sunday ...
From $643 per night (USD)VRBO
- From $400 per night (USD)
Expedia
The Secret Grotto
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to The Secret Grotto! This spacious 3,220 square foot home is located on nearly a 5,000 square foot lot and fea ...
From $400 per night (USD)Expedia
- From $700 per night (USD)
VRBO
The Gideon Lowe House - Old Town Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $700 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $300 per night (USD)Expedia
- From $1028 per night (USD)
VRBO
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1028 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Oceanfront Condo at Hyatt Windward Pointe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You won't find a better steal than a high-season stay in this beautiful and spacious second-floor condo on the Hyatt Win ...
From $700 per night (USD)Expedia
- From $112 per night (USD)
VRBO
One bedroom in the heart of downtown w\/ kitchen
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Truman @ Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $112 per night (USD)VRBO
- From $507 per night (USD)
VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $507 per night (USD)VRBO
- From $899 per night (USD)
VRBO
Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the G ...
From $899 per night (USD)VRBO
- From $347 per night (USD)
VRBO
💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please contact the owner for stays less than 28 days before you try to book. Military Vouchers are Welcome! In Key We ...
From $347 per night (USD)VRBO
- From $719 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King 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 $719 per night (USD)VRBO
- From $307 per night (USD)
VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $307 per night (USD)VRBO
- From $215 per night (USD)
VRBO
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $215 per night (USD)VRBO
- From $908 per night (USD)
Expedia
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $908 per night (USD)Expedia
- From $1786 per night (USD)
VRBO
3\/4 Time: Oceanfront, luxury home with private pool & lush landscaping
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $1786 per night (USD)VRBO
- From $1820 per night (USD)
Expedia
Southern Comfort: Luxury Waterfront Home with private pool & lush landscaping
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1820 per night (USD)Expedia
- From $1814 per night (USD)
VRBO
Paris Mango: Waterfront Luxury Home with Ocean View & Heated Private Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $1814 per night (USD)VRBO
- From $1294 per night (USD)
Expedia
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1294 per night (USD)Expedia
- From $1099 per night (USD)
VRBO
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1099 per night (USD)VRBO
- Click For Pricing
Expedia
Secret Courtyard-2 bedroom 2 bath just steps off Duval street.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Secret Courtyard Cottage is truly the best kept secret in Key West. Recently renovated, this small historic cigar maker ...
Click For PricingExpedia
- Click For Pricing
Expedia
The Hollinsed House | Harvey`s Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Ideally located at the Hollinsed House o ...
Click For PricingExpedia
- From $287 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $287 per night (USD)Expedia