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From $334 per night (USD)
VRBO
Conch Republic Consul General's Cottage.-Historic District
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $334 per night (USD)
VRBO
From $608 per night (USD)
VRBO
** Waterfront - Two Blocks From Duval Street & Mallory Square**
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This condo located right on the water in Building 5 (Unit 531) - top floor - at the Hyatt Sunset Harbor, is a 2 bedroom, ...
From $608 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Private Home- Sun-filled Pool- Neighborhood Water Inlet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and c ...
From $261 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Conch Republic Consul General's Cottage.-Pool-Historic District-Assigned Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $319 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Steps To The Beach And The Sunrise-No Contact Check-In
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnis ...
From $334 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Stone Throw Famous Duval Street Location-No Contact Check-In
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $240 per night (USD)
Expedia
From $667 per night (USD)
VRBO
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunday to Sunday WEEK available to book. Limited Boat Slip available onsite. Must be reserved in advance after reserva ...
From $667 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Historic District-Pool View-Duval Street-Beach Nearby-No Contact Check-In
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2 bedroom, fully furnished condominium with brand new living room furniture and dining room table set is located in ...
From $243 per night (USD)
Expedia
From $431 per night (USD)
VRBO
Colony Sunset- Bright and airy cottage in the heart of old town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in The Colony, a secluded, gated enclave just steps from Duval Street, Colony Sunset is a colorful and relaxing ...
From $431 per night (USD)
VRBO
From $358 per night (USD)
Expedia
A PLEASANT STAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $358 per night (USD)
Expedia
From $496 per night (USD)
VRBO
ANGEL FISH at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropically decorated 2 bedroom 2 bathroom townhouse in secluded area of Truman Annex, complete with updated appliances, ...
From $496 per night (USD)
VRBO
From $652 per night (USD)
Expedia
ABSOLUTE TRUMAN ANNEX in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $652 per night (USD)
Expedia
From $677 per night (USD)
VRBO
TROPICAL EXECUTIVE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $677 per night (USD)
VRBO
From $743 per night (USD)
Expedia
Paradise Island suite-2 bedroom 1 bath, a block off Duval St w/pool, parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $743 per night (USD)
Expedia
From $1152 per night (USD)
VRBO
Bimini suite-3 bedroom 3 bath, a block off Duval St w/pool, parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $1152 per night (USD)
VRBO
Click For Pricing
Expedia
2 BR at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium ...
Click For Pricing
Expedia
From $840 per night (USD)
VRBO
Grand Bahama suite-3 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $840 per night (USD)
VRBO
From $719 per night (USD)
Expedia
Nassau suite-2 bedroom 2 bath, a block off Duval St w/pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: ALL guests staying at the property MUST be 25 years of age or older at this property- NO EXCEPTIONS P ...
From $719 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Conch Republic House - Key West Millionaires Row
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In the center of Key West's prestigious "Millionaires Row," Conch Republic House is a tranquil getaway for up to six in ...
From $212 per night (USD)
VRBO
From $357 per night (USD)
Expedia
SUN, SEA, AND SKY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sun Sea and Sky is blocks from bustling Duval Street, the heart of Old Town Key West, and an easy walk to restaurants, s ...
From $357 per night (USD)
Expedia
From $437 per night (USD)
VRBO
ANGLER'S RETREAT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...
From $437 per night (USD)
VRBO
From $773 per night (USD)
VRBO
🏝️3 Bdrm - Ocean View Every Room-Secluded -Quiet-OCEAN FRONT- 90 FT BALCONY
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
🏝️Thank you for your interest in our stunning Oceanfront 3-bedroom property in Key West! Before proceeding , we kindly ...
From $773 per night (USD)
VRBO
From $391 per night (USD)
VRBO
GREEN BAMBOO at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Paradise! This 2 bedroom townhouse, featuring one bedroom with a king and the second bedroom features twin be ...
From $391 per night (USD)
VRBO
From $612 per night (USD)
Expedia
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: "Island Time" is a newly renovated, 2 bed 2 bath condo located in the gated La Brisa Condominium complex. Situa ...
From $612 per night (USD)
Expedia
From $603 per night (USD)
VRBO
CAPTAINS WHEEL at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home feat ...
From $603 per night (USD)
VRBO
From $681 per night (USD)
Expedia
**WALKING ON SUNSHINE @ THE BEACH** Ocean Condo & Large Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $681 per night (USD)
Expedia
From $447 per night (USD)
VRBO
A LOW TIDE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award winning gated community of the T ...
From $447 per night (USD)
VRBO
Click For Pricing
Expedia
Private luxury retreat all included.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
All included in this large home has a huge master bedroom with 2 walking closets, opens to large wrap around balcony ove ...
Click For Pricing
Expedia
From $783 per night (USD)
VRBO
Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to La Margarita, a newly renovated home with coastal charm only blocks away from Duval Street, the Historic Seap ...
From $783 per night (USD)
VRBO
From $3668 per night (USD)
Expedia
Steps from Duval with Private Pool – Southern Palms
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or ...
From $3668 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Luxurious monthly rental in mid-town
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
28 Day minimum Rental: Secured behind a contemporary privacy fence and an attractive cobblestone driveway is this hidden ...
From $390 per night (USD)
VRBO
From $1751 per night (USD)
Expedia
Key West Suites Hotel # 205
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
From $1751 per night (USD)
Expedia
From $462 per night (USD)
VRBO
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 $462 per night (USD)
VRBO
From $756 per night (USD)
Expedia
A SUNSET AND A HARBOUR VIEW at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, ...
From $756 per night (USD)
Expedia
From $465 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 $465 per night (USD)
VRBO
From $457 per night (USD)
VRBO
Charming Old Town Bungalow
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Charming two story, 3 Bedroom 3 Bathroom. Renovated home built in 1908, on a corner lot in Historical Old Town Key West. ...
From $457 per night (USD)
VRBO
From $1402 per night (USD)
VRBO
Secret Villa I @ Old Town with Private Pool, close to Duval!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1402 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Nan-sea's Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This inviting 2-bedroom, 2-bathroom ground-floor condo is the perfect retreat for one or two couples. The first bedroom ...
From $177 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Elegant Key West Tree House - Walking Distance to Beach and Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Elegant Key West Tree House is a unique monthly rental to stay anytime of the year. Discretely built back off the st ...
From $205 per night (USD)
VRBO
From $481 per night (USD)
Expedia
SERENDIPITY ~ Grand 4 Bedroom/4.5 Bathroom Home in Heart of Key West!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
TIME TO CREATE LIFELONG MEMORIES… Your long-awaited island retreat is sure to have all expectations exceeded within this ...
From $481 per night (USD)
Expedia
From $1419 per night (USD)
VRBO
3-Story spacious conch style home w/ private pool & dock!
Bedrooms:
3
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 $1419 per night (USD)
VRBO
From $781 per night (USD)
VRBO
2BR Condo - Hyatt Beach House Resort - Private Beach - Resort Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key Wes ...
From $781 per night (USD)
VRBO
Click For Pricing
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 $450 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 $450 per night (USD)
Expedia
From $463 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 $463 per night (USD)
VRBO
From $436 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 $436 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Unique Home with loft @ Truman Annex
Bedrooms:
1
Bathrooms:
1
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 $302 per night (USD)
VRBO
From $224 per night (USD)
Expedia
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 $224 per night (USD)
Expedia
From $491 per night (USD)
VRBO
MARLIN BLUE in the Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $491 per night (USD)
VRBO
From $433 per night (USD)
Expedia
COOL BREEZE @ the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** This community is loc ...
From $433 per night (USD)
Expedia
From $380 per night (USD)
VRBO
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 $380 per night (USD)
VRBO
From $460 per night (USD)
Expedia
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 $460 per night (USD)
Expedia
From $415 per night (USD)
VRBO
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 $415 per night (USD)
VRBO
Click For Pricing
Expedia
Classic Key West condo w/ private parking, covered porches, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
Expedia
From $658 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 $658 per night (USD)
VRBO
From $701 per night (USD)
Expedia
Aah PARADISE at the Truman Annex in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AAH PARADISE This Foundry townhome is a Bostonian style 3 level home located in Old Town Key West. This home has been re ...
From $701 per night (USD)
Expedia
From $427 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 $427 per night (USD)
VRBO
From $598 per night (USD)
Expedia
A LICENSE TO CHILL in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...
From $598 per night (USD)
Expedia
From $281 per night (USD)
VRBO
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 $281 per night (USD)
VRBO
From $1148 per night (USD)
Expedia
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 $1148 per night (USD)
Expedia
From $463 per night (USD)
VRBO
AMBERJACK at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $463 per night (USD)
VRBO
From $1132 per night (USD)
Expedia
CATCH OF THE DAY at The Truman Annex in Key West
Bedrooms:
2
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 $1132 per night (USD)
Expedia
From $452 per night (USD)
VRBO
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 $452 per night (USD)
VRBO
From $169 per night (USD)
Expedia
PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. One of ...
From $169 per night (USD)
Expedia
From $669 per night (USD)
VRBO
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 $669 per night (USD)
VRBO
From $381 per night (USD)
Expedia
**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 $381 per night (USD)
Expedia
From $479 per night (USD)
VRBO
La Brisa - Ocean Views Across from Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy beautiful views of the Atlantic Ocean while sitting on your private porch. Located in the scenic La Brisa complex, ...
From $479 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Really Nice completely updated private home in Old Town with private pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently renovated, bright, cheerful and beautifully decorated 1200 square foot. This is a 3 bedroom, 2 bath home with p ...
From $250 per night (USD)
VRBO
From $1087 per night (USD)
VRBO
Pool, Parking, & Pet Friendly - Sunnyside Up
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Summary: Sunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s "Old Town." With an op ...
From $1087 per night (USD)
VRBO
From $2103 per night (USD)
VRBO
~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
THE PROPERTY: Villa Josine not only has curb appeal but also is a stunning example of a Key West eyebrow house. This arc ...
From $2103 per night (USD)
VRBO
Click For Pricing
VRBO
Atlantic Paradise Escape | Luxury Oceanfront Condo in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
Click For Pricing
VRBO
From $1422 per night (USD)
Expedia
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1422 per night (USD)
Expedia
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 $408 per night (USD)
VRBO
Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Dade County pine house has a strong connection to the sea. It was built in 1910 by ship's carpenters and owned for ...
From $408 per night (USD)
VRBO
From $774 per night (USD)
VRBO
PARADISE ON THE OCEANat The Truman Annex in Key West
Bedrooms:
2
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 $774 per night (USD)
VRBO
From $467 per night (USD)
Expedia
A SUNRISE COTTAGE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
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 $467 per night (USD)
Expedia
From $441 per night (USD)
VRBO
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals in 202 ...
From $441 per night (USD)
VRBO
From $413 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 $413 per night (USD)
Expedia
From $333 per night (USD)
VRBO
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 $333 per night (USD)
VRBO
From $372 per night (USD)
Expedia
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 $372 per night (USD)
Expedia
From $341 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 $341 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $309 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 $309 per night (USD)
VRBO
From $957 per night (USD)
Expedia
Private Parking, Heated Pool - Sweet Caroline
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $957 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Private Parking , Heated Pool - Key Lime Cottage
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 $407 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Heated Pool, Epic Location - Sugar Pie Suite
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 $355 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Heated Pool, Epic Location - Honeybun Hideaway
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 $341 per night (USD)
VRBO
From $607 per night (USD)
Expedia
Private Parking, Heated Pool - Banana Split
Bedrooms:
1
Bathrooms:
1
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 $607 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Heated Pool, Private Parking - Creme Brulee Suite
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 $386 per night (USD)
VRBO
From $1317 per night (USD)
Expedia
Villa Déjà vu Key West - Steps Off Duval w Private Pool
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get ...
From $1317 per night (USD)
Expedia
From $609 per night (USD)
VRBO
COLORFUL COCKTAIL in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your perfect Key West getaway! Nestled in the coveted Shipyard community of Truman Annex, this beautifully ma ...
From $609 per night (USD)
VRBO
From $696 per night (USD)
Expedia
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + 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! When explorin ...
From $696 per night (USD)
Expedia
From $674 per night (USD)
VRBO
A PALM OASIS at The Truman Annex in Key West.....
Bedrooms:
2
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 $674 per night (USD)
VRBO
From $371 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 $371 per night (USD)
VRBO
From $633 per night (USD)
VRBO
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $633 per night (USD)
VRBO
From $403 per night (USD)
VRBO
Sunrise 103-2BR/2BA condo near beaches with pool, parking, balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $403 per night (USD)
VRBO
From $241 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 $241 per night (USD)
VRBO
From $406 per night (USD)
Expedia
MONTHLY RENTAL, Thanksgiving 25 open, block to Duval, POOL, personal resort
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 $406 per night (USD)
Expedia
From $1393 per night (USD)
VRBO
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KEY WEST IN STYLE... Imagine carefree days in the tropics, spent in the comfort of this exceptionally located retreat wi ...
From $1393 per night (USD)
VRBO
From $633 per night (USD)
Expedia
New Listing- Modern & spacious historic home with private pool and parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover paradise at Brisa Azul (Blue Breeze), an exquisite historic home nestled in the heart of Old Town Key West. Thi ...
From $633 per night (USD)
Expedia

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