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$Amazing Stay in the Key West! Premium Ocean View w\/ King Bed, Outdoor Pool$
From $306 per night (USD)
VRBO
Amazing Stay in the Key West! Premium Ocean View w\/ King Bed, Outdoor Pool
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 $306 per night (USD)
VRBO
$Perfect Location for Your Next Getaway! Amazing Room w\/ King Bed, Outdoor Pool$
From $229 per night (USD)
VRBO
Perfect Location for Your Next Getaway! Amazing Room w\/ King Bed, Outdoor Pool
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 $229 per night (USD)
VRBO
From $325 per night (USD)
VRBO
Dream Vacation! Fantastic Panoramic Ocean View Room, Outdoor Pool
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 $325 per night (USD)
VRBO
$Short Drive to the Nearest Beach! Amazing Deluxe Room w\/ Amazing Pool View$
From $313 per night (USD)
VRBO
Short Drive to the Nearest Beach! Amazing Deluxe Room w\/ Amazing Pool View
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 $313 per night (USD)
VRBO
$Fantastic Beach Vacation! Amazing Room, 2 Queen Beds, Pool w\/ Sun Loungers$
From $337 per night (USD)
VRBO
Fantastic Beach Vacation! Amazing Room, 2 Queen Beds, Pool w\/ Sun Loungers
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 $337 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Rare Find! 2 Comfortable Rooms In The Heart Of Key West Minutes From The 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 $528 per night (USD)
VRBO
From $259 per night (USD)
VRBO
Look No More! Perfect for a Getaway! Close to Nearest Beach, Outdoor Pool
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 $259 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Perfect Location! Spacious Deluxe Pool View, Outdoor Swimming Pool
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 $305 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Beautiful Key West! Close to the Beach! Amazing Ocean View, Outdoor Pool
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 $289 per night (USD)
VRBO
From $316 per night (USD)
VRBO
Escape To Paradise in Key West! Relaxing Room, Minutes Away From The Beach!
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 $316 per night (USD)
VRBO
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Expedia
KEY WEST - Weekly Stay Only - 2 Bedroom 2 Bathrooms Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Coconut Mallory Marina and Resort is located in the southernmost city in the continental United States. Key West, Fl ...
Click For Pricing
Expedia
From $446 per night (USD)
Expedia
PELICAN'S PERCH at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town neighborhood ...
From $446 per night (USD)
Expedia
From $379 per night (USD)
VRBO
ANNIE'S HIDEAWAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...
From $379 per night (USD)
VRBO
From $798 per night (USD)
VRBO
Exquisite Elegance in Old Town Key West: Your Stylish Sanctuary Awaits
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This stylish Conch home is tucked away on a quiet lane in Old Town Key West. Newly remodeled, impressively decorated 3 B ...
From $798 per night (USD)
VRBO
$Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!$
From $1440 per night (USD)
VRBO
Seafarer's Refuge: 3 Story spacious conch style home w\/ private pool & dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1440 per night (USD)
VRBO
From $411 per night (USD)
Expedia
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. Pets welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $411 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Carriage House at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $350 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Bunk Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $377 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Unique Home with loft @ Truman Annex
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $313 per night (USD)
VRBO
From $411 per night (USD)
Expedia
MARLIN BLUE in the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $411 per night (USD)
Expedia
From $359 per night (USD)
VRBO
COOL BREEZE @ the Key West Golf Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...
From $359 per night (USD)
VRBO
From $337 per night (USD)
Expedia
TROPICAL BREEZES at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $337 per night (USD)
Expedia
From $408 per night (USD)
VRBO
MANATEE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $408 per night (USD)
VRBO
From $364 per night (USD)
Expedia
ISLAND TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $364 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $210 per night (USD)
VRBO
$Classic Key West condo w\/ private parking, covered porches, & shared pool$
From $695 per night (USD)
Expedia
Classic Key West condo w\/ private parking, covered porches, & shared pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $695 per night (USD)
Expedia
$**LAYOVER in PARADISE @ CASA MARINA** New Home \/ Pool + LAST KEY SERVICES…$
From $485 per night (USD)
VRBO
**LAYOVER in PARADISE @ CASA MARINA** New Home \/ Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! A home design ...
From $485 per night (USD)
VRBO
From $551 per night (USD)
Expedia
AAH PARADISE at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
AAH PARADISE This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been r ...
From $551 per night (USD)
Expedia
From $538 per night (USD)
VRBO
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Note: In 2026, bookings will require a minimum stay of 28 days, starting on the first of the month. I can adjust the dat ...
From $538 per night (USD)
VRBO
From $520 per night (USD)
Expedia
A LICENSE TO CHILL in the Truman Annex
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...
From $520 per night (USD)
Expedia
From $1214 per night (USD)
VRBO
**BAHAMIAN BLUES @ BAHAMA VILLAGE** Impeccable Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! BAHAMIAN BLUE ...
From $1214 per night (USD)
VRBO
$Quaint Island Escape Condo w\/Spacious Balcony Deck in Beautiful Truman Annex$
From $275 per night (USD)
Expedia
Quaint Island Escape Condo w\/Spacious Balcony Deck in Beautiful Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental ...
From $275 per night (USD)
Expedia
From $1153 per night (USD)
VRBO
DOLPHIN WATCH in Key West @ The Truman Annex Compass Realty
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attrac ...
From $1153 per night (USD)
VRBO
From $441 per night (USD)
Expedia
AMBERJACK at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $441 per night (USD)
Expedia
From $914 per night (USD)
VRBO
CATCH OF THE DAY at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Tr ...
From $914 per night (USD)
VRBO
From $396 per night (USD)
Expedia
SOUTHARD COMFORT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beau ...
From $396 per night (USD)
Expedia
$Colorful cottage w\/shared pool, central AC, washer\/dryer$
From $305 per night (USD)
VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $305 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $759 per night (USD)
Expedia
From $476 per night (USD)
VRBO
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! DOCKSIDE DAYD ...
From $476 per night (USD)
VRBO
From $989 per night (USD)
Expedia
Pool, Parking, & Pet Friendly - Sunnyside Up
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Sunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s "Old Town." With an op ...
From $989 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Atlantic Paradise Escape | Luxury Oceanfront Condo in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Paradise Escape | Luxury Oceanfront Condo in Key West Monthly Rental | Unit MC322 | 2BR, 2BA | Direct Ocean Vi ...
From $205 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Lovely 2 bedroom, 2 bathroom steps from the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Key West at La Brisa, a gated Condo community, just steps from the beach on Key West's Atlantic coast. Walk in ...
From $345 per night (USD)
VRBO
From $660 per night (USD)
VRBO
PARADISE ON THE OCEANat The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $660 per night (USD)
VRBO
From $453 per night (USD)
Expedia
A SUNRISE COTTAGE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...
From $453 per night (USD)
Expedia
From $427 per night (USD)
VRBO
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to "Cocktails & Dreams," an impeccably updated second-floor condo located in the coveted Shipyard Condominiums! ...
From $427 per night (USD)
VRBO
From $364 per night (USD)
Expedia
ALMOST PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $364 per night (USD)
Expedia
From $3014 per night (USD)
VRBO
Private Heated Pool & Near Duval - The Curry House
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $3014 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 6
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Curry House offers three stories of historic Conch house charm, perfect for your getaway. This guesthouse featu ...
From $353 per night (USD)
Expedia
From $529 per night (USD)
VRBO
Balcony, Pool, Near Duval - Curry House Room 3 + 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Curry House offers three stories of historic charm, transporting you back in time. The guesthouse features priv ...
From $529 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $353 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 8
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $348 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 7
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $371 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $357 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 9
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $293 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Curry House | Heated Pool, King Bed, 1st Floor
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $353 per night (USD)
VRBO
From $895 per night (USD)
Expedia
Sweet Caroline | Banana's Foster Guesthouse
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $895 per night (USD)
Expedia
From $393 per night (USD)
VRBO
KeyLime Cottage | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $393 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Sugar Pie Suite | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $351 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Honeybun Hideaway at Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $371 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Banana Split | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $527 per night (USD)
Expedia
From $480 per night (USD)
VRBO
Creme Brulee Suite | Banana's Foster Guesthouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $480 per night (USD)
VRBO
From $502 per night (USD)
Expedia
COLORFUL COCKTAIL in the Truman Annex
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This Shipyard unit is a two level condominium which has a private courtyard with a deck to enjoy the beautiful weather a ...
From $502 per night (USD)
Expedia
From $825 per night (USD)
VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + 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! When explorin ...
From $825 per night (USD)
VRBO
From $594 per night (USD)
Expedia
A PALM OASIS at The Truman Annex in Key West.....
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
NEW LISTING!!! This charming two bedroom, two and one half bath townhome has recently been updated and added to our rent ...
From $594 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Coastal Inspired Cottage in Bahama Village Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...
From $437 per night (USD)
VRBO
$Colorful beachfront condo w\/ ocean view balcony & shared hot tub\/pool\/tennis$
From $784 per night (USD)
Expedia
Colorful beachfront condo w\/ ocean view balcony & shared hot tub\/pool\/tennis
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $784 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Key Rest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $227 per night (USD)
VRBO
$MONTHLY RENTAL, block to Duval, POOL, your own personal resort, 3 BR\/ 3 BA$
From $238 per night (USD)
Expedia
MONTHLY RENTAL, block to Duval, POOL, your own personal resort, 3 BR\/ 3 BA
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...
From $238 per night (USD)
Expedia
From $334 per night (USD)
VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $334 per night (USD)
VRBO
From $506 per night (USD)
Expedia
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...
From $506 per night (USD)
Expedia
From $298 per night (USD)
VRBO
ISLAND TIME at Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Island Time***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome back ...
From $298 per night (USD)
VRBO
From $571 per night (USD)
Expedia
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block t ...
From $571 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Extended Summer Stays for 2025- Open 6 months from April 1st onwards
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $156 per night (USD)
VRBO
From $652 per night (USD)
Expedia
**THE BEAMING BARRACUDA @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERV
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...
From $652 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Hyatt Beach House! Quiet Key West Location! Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $626 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $626 per night (USD)
Expedia
From $394 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $394 per night (USD)
VRBO
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Expedia
Studio at Hyatt Residence Club Key West, Sunset Harbor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Seth Nock Licensed Broker, Selling Timeshares INC. Studio at Hyatt Residence Club Key West, Sunset Harbor. Check-in: ...
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Expedia
From $304 per night (USD)
VRBO
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $304 per night (USD)
VRBO
From $300 per night (USD)
Expedia
TAILGATE KEY at the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $300 per night (USD)
Expedia
From $512 per night (USD)
VRBO
SWEET'S SPOT at The Truman Annex in Key West
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $512 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Red Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $479 per night (USD)
Expedia
From $364 per night (USD)
VRBO
BEST TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...
From $364 per night (USD)
VRBO
From $646 per night (USD)
Expedia
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The moment yo ...
From $646 per night (USD)
Expedia
From $417 per night (USD)
VRBO
POOLSIDE HANGOVER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy yo ...
From $417 per night (USD)
VRBO
From $1282 per night (USD)
Expedia
A Place on Emma at the Truman Annex in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1282 per night (USD)
Expedia
From $329 per night (USD)
VRBO
A DUCK ON THE GREEN at the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $329 per night (USD)
VRBO
From $337 per night (USD)
Expedia
SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $337 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Shared Pool & Near Duval - Road's End
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Located just a stone's throw from Mile Marker Zero, "Road's End" is a charming 1-bedroom, 1.5-bath townhome in ...
From $567 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $315 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $213 per night (USD)
VRBO
$Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w\/ pool$
From $574 per night (USD)
Expedia
Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w\/ pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $574 per night (USD)
Expedia
$Captain's Daughter: Oversized home for the whole family w\/private pool & dock$
From $1705 per night (USD)
VRBO
Captain's Daughter: Oversized home for the whole family w\/private pool & dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1705 per night (USD)
VRBO
From $431 per night (USD)
Expedia
HIGH TIDE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $431 per night (USD)
Expedia
From $408 per night (USD)
VRBO
A CONCH ESCAPE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $408 per night (USD)
VRBO
From $393 per night (USD)
Expedia
A SUNSET VIEW at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $393 per night (USD)
Expedia
From $1063 per night (USD)
VRBO
Spacious home with pool & balcony - 1 block from Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $1063 per night (USD)
VRBO
From $174 per night (USD)
Expedia
Charming home in Old Town, walk to shops & restaurants - yard
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Gingerbread Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $174 per night (USD)
Expedia
Click For Pricing
VRBO
GYPSY'S PALACE in the Truman Annex - Stunning ocean views!!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
Click For Pricing
VRBO
From $441 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $441 per night (USD)
Expedia

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