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From $632 per night (USD)
VRBO
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 $632 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $349 per night (USD)
VRBO
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 $349 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $395 per night (USD)
VRBO
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 $395 per night (USD)
VRBO
From $354 per night (USD)
Expedia
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 $354 per night (USD)
Expedia
From $664 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 $664 per night (USD)
VRBO
Click For Pricing
Expedia
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
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 $518 per night (USD)
Expedia
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 $518 per night (USD)
Expedia
From $717 per night (USD)
VRBO
**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 $717 per night (USD)
VRBO
From $666 per night (USD)
Expedia
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 $666 per night (USD)
Expedia
From $436 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 $436 per night (USD)
VRBO
From $650 per night (USD)
Expedia
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 $650 per night (USD)
Expedia
From $168 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 $168 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 $334 per night (USD)
VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
Bedrooms:
4
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 $187 per night (USD)
Expedia
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautifully home with quaint charm has a one month minimum stay requirement because of local zoning regulation. Col ...
From $187 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Extended Summer Stays for 2025- Open 6 months from April 1st onwards
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $187 per night (USD)
VRBO
From $516 per night (USD)
Expedia
**THE BEAMING BARRACUDA @ THE FOUNDRY** Near Duval & Beach + 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! THE BEAMING B ...
From $516 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Hyatt Beach House! Quiet Key West Location! Sleeps 6
Bedrooms:
2
Bathrooms:
2
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 $773 per night (USD)
Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
Bedrooms:
2
Bathrooms:
2
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 $773 per night (USD)
Expedia
From $320 per night (USD)
VRBO
ISLAND TIME at Key West Golf Club
Bedrooms:
2
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 $320 per night (USD)
VRBO
From $512 per night (USD)
Expedia
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
Bedrooms:
1
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 $512 per night (USD)
Expedia
From $534 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 $534 per night (USD)
VRBO
From $307 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 $307 per night (USD)
Expedia
From $508 per night (USD)
VRBO
SWEET'S SPOT at The Truman Annex in Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $508 per night (USD)
VRBO
Click For Pricing
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: ...
Click For Pricing
Expedia
From $304 per night (USD)
VRBO
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
2
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 $336 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 $336 per night (USD)
Expedia
From $356 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 $356 per night (USD)
VRBO
From $387 per night (USD)
Expedia
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The moment yo ...
From $387 per night (USD)
Expedia
From $424 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 $424 per night (USD)
VRBO
From $1353 per night (USD)
Expedia
A Place on Emma at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1353 per night (USD)
Expedia
From $363 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 $363 per night (USD)
VRBO
From $380 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 $380 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Steps from Duval, Shared Pool - Road's End
Bedrooms:
1
Bathrooms:
1
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 $430 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $196 per night (USD)
Expedia
From $192 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 $192 per night (USD)
VRBO
From $468 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 $468 per night (USD)
Expedia
From $1299 per night (USD)
VRBO
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 $1299 per night (USD)
VRBO
From $441 per night (USD)
Expedia
HIGH TIDE at The Truman Annex in Key West
Bedrooms:
1
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 $441 per night (USD)
Expedia
From $463 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 $463 per night (USD)
VRBO
From $413 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 $413 per night (USD)
Expedia
From $367 per night (USD)
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! ...
From $367 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
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 $1082 per night (USD)
Expedia
Click For Pricing
VRBO
Charming home in Old Town, walk to shops & restaurants - yard
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gingerbread Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
VRBO
From $456 per night (USD)
Expedia
ARCHIPELAGO l at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $456 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Old Town Charm Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
From $295 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Location, Beauty & Comfort @ Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $444 per night (USD)
Expedia
From $879 per night (USD)
VRBO
Oceanfront 4-Bed 3-Bath home with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $879 per night (USD)
VRBO
From $437 per night (USD)
Expedia
Alluring corner unit w/ full kitchen & pool - close to beach/ nightlife
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Seaclusion Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $437 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tradewinds at Smathers Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $267 per night (USD)
VRBO
From $821 per night (USD)
Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $821 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $468 per night (USD)
VRBO
From $3155 per night (USD)
Expedia
Takeover at the Grand Maloney
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3155 per night (USD)
Expedia
From $910 per night (USD)
VRBO
BLUE LAGOON at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $910 per night (USD)
VRBO
From $368 per night (USD)
VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)
VRBO
From $1709 per night (USD)
VRBO
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1709 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Sailor's Sanctuary - A Renovated Condo in Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $189 per night (USD)
Expedia
From $520 per night (USD)
VRBO
Hidden Beach - the perfect place to stay in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 3 - In Old Town, just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. ...
From $520 per night (USD)
VRBO
From $1959 per night (USD)
VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $1959 per night (USD)
VRBO
From $879 per night (USD)
VRBO
ARCHIPELAGO in the Truman Annex
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $879 per night (USD)
VRBO
From $677 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $677 per night (USD)
Expedia
From $709 per night (USD)
VRBO
AQUA BREEZE at 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 $709 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Hidden Beach Unit 1. The perfect place to stay in Key West for less
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $538 per night (USD)
Expedia
From $415 per night (USD)
VRBO
SHADY NOOK at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll enjoy bright, ...
From $415 per night (USD)
VRBO
From $244 per night (USD)
Expedia
A PALM TREE PARADISE @ the Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $244 per night (USD)
Expedia
From $411 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in the heart of Old Town within the sought-after Shipyard community, this inviting second-floor condo offers the ...
From $411 per night (USD)
VRBO
From $930 per night (USD)
Expedia
A GULFSTREAM DRIFT at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $930 per night (USD)
Expedia
From $506 per night (USD)
VRBO
LIFE IN THE SLOW LANE at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $506 per night (USD)
VRBO
From $677 per night (USD)
Expedia
SALTWATER ANGLER at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $677 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Island Breezes at The Truman Annex in Key West@ the Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $388 per night (USD)
VRBO
From $780 per night (USD)
Expedia
A HARBOUR ROOST at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $780 per night (USD)
Expedia
From $399 per night (USD)
VRBO
A SANCTUARY HOME at the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...
From $399 per night (USD)
VRBO
From $442 per night (USD)
Expedia
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautiful gated home is located on an oversized corner lot a few blocks from White Street Pier and Higg's Beach wit ...
From $442 per night (USD)
Expedia
From $466 per night (USD)
VRBO
**ASCENSION** @ The Truman Annex Compass Realty
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $466 per night (USD)
VRBO
From $449 per night (USD)
Expedia
DANCING PALMS at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Leave the c ...
From $449 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For Pricing
VRBO
From $538 per night (USD)
Expedia
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $538 per night (USD)
Expedia
From $704 per night (USD)
VRBO
OCEAN BREEZE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $704 per night (USD)
VRBO
From $493 per night (USD)
Expedia
SAGO PALM at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $493 per night (USD)
Expedia
From $1996 per night (USD)
VRBO
Features.Key West Suites Hotel has an outdoor pool and fitness center
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 ...
From $1996 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $391 per night (USD)
Expedia
From $636 per night (USD)
VRBO
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $636 per night (USD)
VRBO
From $448 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $448 per night (USD)
VRBO
From $1051 per night (USD)
VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $1051 per night (USD)
VRBO
From $753 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W/ 4+ Bedrooms/ 5.5 Baths
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $753 per night (USD)
VRBO
From $506 per night (USD)
VRBO
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $506 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $456 per night (USD)
Expedia
From $629 per night (USD)
VRBO
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
28 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $629 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Prime location, stunning views from 2 decks—walk or ride to explore the island!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $400 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $506 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nice quiet landing a few blocks from the action on Duval Street. This is a Saturday-Saturday weekly home for the rest of ...
From $202 per night (USD)
Expedia
From $801 per night (USD)
VRBO
Waterfront 4 Bed 4 Bath Home in Key Cove Landings
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $801 per night (USD)
VRBO
From $287 per night (USD)
Expedia
GOLF VILLA - Monthly Rental - 2BD/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $287 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $371 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Sea Breeze at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sea Breeze at 1800 Atlantic is a two bedroom / two bathroom fully furnished condo located in the East Tower on the top f ...
From $284 per night (USD)
Expedia
From $529 per night (USD)
VRBO
Balcony, Pool, & Pet Friendly - St. Martin Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $529 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Newly Updated! The Grand Cayman Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $526 per night (USD)
Expedia

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