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From $706 per night (USD)
VRBO
Perfect Staycation! Two Convenient Rooms, Onsite Pool, Minutes to Closest Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $706 per night (USD)
VRBO
From $1150 per night (USD)
VRBO
Perfect Staycation! Four Spacious Rooms, Outdoor Swimming 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 $1150 per night (USD)
VRBO
$Perfect staycation! Four Gorgeous Spaces (w\/ 2 Queen Beds Each), Outdoor Pool$
From $969 per night (USD)
VRBO
Perfect staycation! Four Gorgeous Spaces (w\/ 2 Queen Beds Each), Outdoor Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $969 per night (USD)
VRBO
From $1294 per night (USD)
VRBO
Perfect Key West Staycation Perfect For Your Family! Four Relaxing Rooms, Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1294 per night (USD)
VRBO
From $1271 per night (USD)
VRBO
Perfect Beach Getaway! Four Convenient Rooms, Driving Distance to the Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1271 per night (USD)
VRBO
From $727 per night (USD)
VRBO
Perfect staycation! 3 Convenient Spaces, Close to Amazing Beach, Outdoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $727 per night (USD)
VRBO
From $1060 per night (USD)
VRBO
Ideal Location! Three Spacious Spaces, Close to Beach, Outdoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1060 per night (USD)
VRBO
From $954 per night (USD)
VRBO
Beach Getaway For Family and Friends! 3 Spacious Ocean View Rooms, Outdoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $954 per night (USD)
VRBO
From $1446 per night (USD)
VRBO
Amazing Land and Sea Getaway! Four Convenient Rooms, Close to Nearest Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1446 per night (USD)
VRBO
From $1131 per night (USD)
VRBO
Ideal Location for Family and Friends! Four Spacious Rooms, Outdoor Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $1131 per night (USD)
VRBO
$FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest$
From $472 per night (USD)
VRBO
FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
WELCOME TO FOUNDRY 7! Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find ...
From $472 per night (USD)
VRBO
$THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba\/ 1Ba Unit in The Shipyard!$
From $351 per night (USD)
Expedia
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba\/ 1Ba Unit in The Shipyard!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighb ...
From $351 per night (USD)
Expedia
From $544 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 $544 per night (USD)
VRBO
From $884 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 $884 per night (USD)
VRBO
$Classic Key West living w\/ a full kitchen, balcony, & shared pool$
From $586 per night (USD)
VRBO
Classic Key West living w\/ a full kitchen, balcony, & shared pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $586 per night (USD)
VRBO
From $287 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 $287 per night (USD)
Expedia
From $1008 per night (USD)
VRBO
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
2
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 $1008 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Looking for Relaxing Location for Your Next Getaway? Premium Ocean View Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our tropical oasis, where modern comfort meets Key West charm. Our family-friendly room boasts newly decorate ...
From $335 per night (USD)
VRBO
$MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated private pool, and close to Duval!$
From $999 per night (USD)
VRBO
MANGO MARGARITA~ 2 bedroom\/2.5 bath, heated private pool, and close to Duval!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
LOCATION LOCATION LOCATION... Enjoy this convenient Old Town Location. Located a block from Duval and a short walk or b ...
From $999 per night (USD)
VRBO
From $1198 per night (USD)
Expedia
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Bedrooms:
2
Bathrooms:
4
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 $1198 per night (USD)
Expedia
$CONCH HEAVEN ~ Stylish 2B\/2Ba, Sleeps 6 in Old Town w\/ Heated Cocktail Pool!$
From $956 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 $956 per night (USD)
VRBO
From $1110 per night (USD)
Expedia
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms. Open the rear French doors to a p ...
From $1110 per night (USD)
Expedia
From $358 per night (USD)
VRBO
SEA LA VIE ~ Living in Complete Luxury in This Elegant Three Story Home!
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town. This home is elegant, yet quite the tropical del ...
From $358 per night (USD)
VRBO
From $332 per night (USD)
Expedia
ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pass by from ...
From $332 per night (USD)
Expedia
From $1362 per night (USD)
VRBO
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...
From $1362 per night (USD)
VRBO
From $1256 per night (USD)
Expedia
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $1256 per night (USD)
Expedia
$STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!$
From $1285 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 $1285 per night (USD)
VRBO
From $2326 per night (USD)
Expedia
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 $2326 per night (USD)
Expedia
$SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!$
From $1179 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
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 $1179 per night (USD)
VRBO
From $572 per night (USD)
Expedia
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $572 per night (USD)
Expedia
From $229 per night (USD)
VRBO
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
IMMACULATE RETREAT... Beautifully designed townhouse located in the Southernmost Cabana Community of Key West just steps ...
From $229 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
Bedrooms:
2
Bathrooms:
5
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 $1067 per night (USD)
Expedia
$ATLANTIC BREEZE ~ 2B\/2BA Renovated Retreat w\/ Pool, Fitness Area & Beach!$
From $642 per night (USD)
VRBO
ATLANTIC BREEZE ~ 2B\/2BA Renovated Retreat w\/ Pool, Fitness Area & Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BEACHES ON BOTH SIDES... This newly renovated two bedroom condo is close to the airport, beaches, restaurants and minute ...
From $642 per night (USD)
VRBO
From $278 per night (USD)
Expedia
HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ISLAND TIME AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms, a privat ...
From $278 per night (USD)
Expedia
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!$
From $531 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
'La Dolce Vita' is located in Old Town, Key West!! Just 3 short blocks to Southernmost Beach and Southernmost Po ...
From $531 per night (USD)
VRBO
From $417 per night (USD)
Expedia
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ADORING RETREAT ONE BLOCK FROM DUVAL… One bedroom gem on Simonton Street one block from Duval. One bedroom, one bathroo ...
From $417 per night (USD)
Expedia
Click For Pricing
VRBO
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coas ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Luxurious top floor, end unit, within premier resort on the Atlantic Ocean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax in style at the Hyatt Windward Pointe Resort. This is the best location within the resort: Top floor, end unit. Lo ...
Click For Pricing
Expedia
$Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!$
From $357 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 $357 per night (USD)
VRBO
$Gulf Getaway | Condo w\/Pool!$
From $278 per night (USD)
Expedia
Gulf Getaway | Condo w\/Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $278 per night (USD)
Expedia
From $543 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 $543 per night (USD)
VRBO
$GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!$
From $1080 per night (USD)
Expedia
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 $1080 per night (USD)
Expedia
From $470 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 $470 per night (USD)
VRBO
From $1132 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $1132 per night (USD)
Expedia
From $1142 per night (USD)
VRBO
Washer & Dryer, Near Downtown - The Mesa House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $1142 per night (USD)
VRBO
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $595 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $595 per night (USD)
Expedia
$BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!$
From $206 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 $206 per night (USD)
VRBO
$LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!$
From $211 per night (USD)
Expedia
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
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 $211 per night (USD)
Expedia
From $378 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 retreat is nestled in the highly sought-after neighborhood of The Meado ...
From $378 per night (USD)
VRBO
From $153 per night (USD)
Expedia
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
Bedrooms:
1
Bathrooms:
2
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 $153 per night (USD)
Expedia
From $855 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $855 per night (USD)
VRBO
Click For Pricing
Expedia
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
Expedia
From $814 per night (USD)
VRBO
Balcony & Near Downtown - Cloud Suite on Duval
Bedrooms:
3
Bathrooms:
3
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 $814 per night (USD)
VRBO
From $775 per night (USD)
Expedia
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 $775 per night (USD)
Expedia
From $275 per night (USD)
VRBO
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 $275 per night (USD)
VRBO
From $377 per night (USD)
Expedia
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 $377 per night (USD)
Expedia
$**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE$
From $1141 per night (USD)
VRBO
**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 $1141 per night (USD)
VRBO
From $484 per night (USD)
Expedia
**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 $484 per night (USD)
Expedia
From $265 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $265 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Book now!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe! **Reservations are available in weekly (7 ...
From $619 per night (USD)
VRBO
From $324 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 $324 per night (USD)
VRBO
$Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking$
From $2064 per night (USD)
Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)
Expedia
From $296 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 $296 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Roosters Perch at Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $434 per night (USD)
Expedia
From $293 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 $293 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Bedrooms:
2
Bathrooms:
3
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 $521 per night (USD)
VRBO
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $534 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 $534 per night (USD)
VRBO
$Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen\n$
From $230 per night (USD)
Expedia
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $230 per night (USD)
Expedia
From $714 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $714 per night (USD)
VRBO
From $611 per night (USD)
Expedia
The Secret Grotto
Bedrooms:
5
Bathrooms:
4
Sleeps:
6
Welcome to The Secret Grotto! This spacious 3,300 square foot home is located on nearly a 5,000 square foot lot and fea ...
From $611 per night (USD)
Expedia
From $974 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 $974 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $434 per night (USD)
Expedia
From $1139 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 $1139 per night (USD)
VRBO
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Expedia
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
3
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 ...
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Expedia
$One bedroom in the heart of downtown w\/ kitchen$
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VRBO
One bedroom in the heart of downtown w\/ kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Truman at Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
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VRBO
From $524 per night (USD)
Expedia
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 $524 per night (USD)
Expedia
From $931 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 $931 per night (USD)
VRBO
From $493 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 $493 per night (USD)
VRBO
From $868 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 $868 per night (USD)
VRBO
From $389 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 $389 per night (USD)
VRBO
From $142 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 $142 per night (USD)
VRBO
From $992 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 $992 per night (USD)
Expedia
$3\/4 Time: Oceanfront, luxury home with private pool & lush landscaping$
From $1126 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 $1126 per night (USD)
VRBO
From $1146 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 $1146 per night (USD)
Expedia
From $1105 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 $1105 per night (USD)
VRBO
From $1378 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 $1378 per night (USD)
Expedia
From $1314 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 $1314 per night (USD)
VRBO
From $366 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 $366 per night (USD)
Expedia
From $999 per night (USD)
VRBO
Craig & Cindy's 4 Bedroom Key West Truman Annex Porter House with private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $999 per night (USD)
VRBO
From $406 per night (USD)
VRBO
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a GATED COMMUNITY across from ...
From $406 per night (USD)
VRBO
$NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes\n$
From $182 per night (USD)
VRBO
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY REDECORATED AS OF APRIL 15. 2025 all dark natural wood walls and cabinets gone instead painted off-white color th ...
From $182 per night (USD)
VRBO
From $723 per night (USD)
Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $723 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Mango Tree Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $132 per night (USD)
VRBO
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Expedia
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
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Expedia
$Curaçao 2BR Condo w\/ Pool & Waterfront Dock$
From $514 per night (USD)
VRBO
Curaçao 2BR Condo w\/ Pool & Waterfront Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring family & friends to this 1200 sqft waterfront condo in historic Old Town Key West. On-site ...
From $514 per night (USD)
VRBO
$Downtown Aruba 2BR\/2BA • Pool, Dock, Pet OK$
From $695 per night (USD)
Expedia
Downtown Aruba 2BR\/2BA • Pool, Dock, Pet OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $695 per night (USD)
Expedia
From $1894 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1894 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Old Town Eleuthera • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $700 per night (USD)
Expedia
From $154 per night (USD)
VRBO
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $154 per night (USD)
VRBO
$Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl$
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Expedia
Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
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Expedia

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