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Key West Rentals
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- From $2746 per night (USD)
VRBO
The Curry House by Brightwild | Historic Guesthome
- 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 $2746 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Curry House #6 by Brightwild | King Bed, Pool
- 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 guest ...
From $275 per night (USD)Expedia
- From $556 per night (USD)
VRBO
Curry House by Brightwild | Balcony & Pool -Rm 3&4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $556 per night (USD)VRBO
- From $283 per night (USD)
Expedia
Curry House Room 1 | Heated Pool & Balcony
- 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 $283 per night (USD)Expedia
- From $274 per night (USD)
VRBO
Curry House #8 by Brightwild | King Bed, Balcony
- 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 $274 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Curry House #7 by Brightwild | King Bed, Balcony
- 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 $267 per night (USD)Expedia
- From $283 per night (USD)
VRBO
Curry House #2 by Brightwild | Balcony & Pool
- 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 $283 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Curry House by Brightwild | Heated Pool - Rm #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 $254 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Curry House Room 5 | 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 $275 per night (USD)VRBO
- From $693 per night (USD)
Expedia
Sweet Caroline by Brightwild | Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $693 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Key Lime Cottage by Brightwild | Pool & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $316 per night (USD)VRBO
- From $316 per night (USD)
Expedia
Sugar Pie Suite by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $316 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Honey Bun Hideaway by Brightwild | Pool & Grill!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $316 per night (USD)VRBO
- From $356 per night (USD)
Expedia
Banana Split by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $356 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Creme Brulee Suite by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $316 per night (USD)VRBO
- From $544 per night (USD)
Expedia
COLORFUL COCKTAIL at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 $544 per night (USD)Expedia
- From $725 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 $725 per night (USD)VRBO
- From $693 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 $693 per night (USD)Expedia
- From $278 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 $278 per night (USD)VRBO
- From $517 per night (USD)
Expedia
Colorful beachfront condo w\/ ocean view balcony & shared hot tub\/pool\/tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $517 per night (USD)Expedia
- From $213 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 $213 per night (USD)VRBO
- From $233 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 $233 per night (USD)Expedia
- From $329 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 30 days prior to your arrival! You don’t oft ...
From $329 per night (USD)VRBO
- From $215 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 $215 per night (USD)Expedia
- From $280 per night (USD)
VRBO
FORE REEL at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fore Reel! Have you ever dreamed of living in a quaint Key West Golfing gated community with so many wonderfu ...
From $280 per night (USD)VRBO
- From $295 per night (USD)
Expedia
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 $295 per night (USD)Expedia
- From $558 per night (USD)
VRBO
~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 $558 per night (USD)VRBO
- From $204 per night (USD)
Expedia
Extended Summer Stays for 2024 available now
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located facing the tranquil lush courtyard at 1800 Atlantic. This spacious family retreat features a renovated kitchen. ...
From $204 per night (USD)Expedia
- From $618 per night (USD)
VRBO
**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 $618 per night (USD)VRBO
- From $674 per night (USD)
Expedia
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 $674 per night (USD)Expedia
- From $674 per night (USD)
VRBO
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 $674 per night (USD)VRBO
- 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
- Click For Pricing
VRBO
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 PricingVRBO
- From $304 per night (USD)
Expedia
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)Expedia
- From $298 per night (USD)
VRBO
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 $298 per night (USD)VRBO
- From $502 per night (USD)
Expedia
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 $502 per night (USD)Expedia
- From $380 per night (USD)
VRBO
Red Room at Grand Maloney Hotel with Pool!
- 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 $380 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Road's End by Brightwild | Steps to Duval St!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Just a stone's throw away from Mile Marker Zero lies the aptly named "Road's End," a charming 1 Bd, 1.5 Bth tow ...
From $422 per night (USD)Expedia
- From $399 per night (USD)
VRBO
BEST TIME at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This Shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and e ...
From $399 per night (USD)VRBO
- From $440 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 30 days prior to your arrival! The moment yo ...
From $440 per night (USD)Expedia
- From $334 per night (USD)
VRBO
African Queen by Brightwild | GREAT Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: African Queen Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seapo ...
From $334 per night (USD)VRBO
- From $352 per night (USD)
Expedia
Pilar's Cottage by Brightwild | Studio w\/Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Pilar Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport distr ...
From $352 per night (USD)Expedia
- From $1720 per night (USD)
VRBO
Harborwalk Hideaways by Brightwild |Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $1720 per night (USD)VRBO
- From $422 per night (USD)
Expedia
POOLSIDE HANGOVER at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away ...
From $422 per night (USD)Expedia
- From $1435 per night (USD)
VRBO
A Place on Emma at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1435 per night (USD)VRBO
- From $380 per night (USD)
Expedia
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 $380 per night (USD)Expedia
- From $392 per night (USD)
VRBO
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 $392 per night (USD)VRBO
- From $191 per night (USD)
Expedia
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed an ...
From $191 per night (USD)Expedia
- From $180 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 $180 per night (USD)VRBO
- From $387 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
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $387 per night (USD)Expedia
- From $1916 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 $1916 per night (USD)VRBO
- From $454 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 $454 per night (USD)Expedia
- From $250 per night (USD)
VRBO
SHELLABRATION at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY***** This prime two bedroom, two and a half bath fully furnished ...
From $250 per night (USD)VRBO
- From $444 per night (USD)
Expedia
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 $444 per night (USD)Expedia
- From $426 per night (USD)
VRBO
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 $426 per night (USD)VRBO
- Click For Pricing
Expedia
GYPSY'S PALACE at The Truman Annex in Key West - 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 PricingExpedia
- From $1130 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 $1130 per night (USD)VRBO
- From $119 per night (USD)
Expedia
Charming home in Old Town, walk to shops & restaurants - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gingerbread Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $119 per night (USD)Expedia
- From $477 per night (USD)
VRBO
ARCHIPELAGO l at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $477 per night (USD)VRBO
- From $291 per night (USD)
Expedia
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 $291 per night (USD)Expedia
- From $448 per night (USD)
VRBO
Location, Beauty & Comfort @ Truman Annex
- Bedrooms:
- 3
- 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 $448 per night (USD)VRBO
- From $749 per night (USD)
Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Like many hig ...
From $749 per night (USD)Expedia
- From $1098 per night (USD)
VRBO
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront 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 $1098 per night (USD)VRBO
- From $435 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 $435 per night (USD)Expedia
- From $276 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 $276 per night (USD)VRBO
- From $380 per night (USD)
Expedia
Sky Loft by Brightwild | Penthouse in Prime Spot!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This gem of a top floor apartment is perfect for your weekend getaway. Sky Loft is located just one block away ...
From $380 per night (USD)Expedia
- From $3928 per night (USD)
VRBO
Takeover at the Grand Maloney by Brightwild
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $3928 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Claude Monet Suite by Brightwild | Pool & Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Micro-efficiency near downtown Key West! The Galleria was once a haven for traveling artists who frequented K ...
From $292 per night (USD)Expedia
- From $967 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 $967 per night (USD)VRBO
- From $441 per night (USD)
Expedia
**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private 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! Look for the ...
From $441 per night (USD)Expedia
- From $2246 per night (USD)
VRBO
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $2246 per night (USD)VRBO
- From $233 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 $233 per night (USD)Expedia
- From $633 per night (USD)
VRBO
Hidden Beach - the perfect place to stay in Key West
- Bedrooms:
- 2
- 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 $633 per night (USD)VRBO
- From $1830 per night (USD)
Expedia
Key West - Historic & Charming - Main House
- 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 $1830 per night (USD)Expedia
- From $2178 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 $2178 per night (USD)VRBO
- Click For Pricing
Expedia
Banyan Resort - 2 Blocks to Sunset Celebration
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed ...
Click For PricingExpedia
- From $940 per night (USD)
VRBO
ARCHIPELAGO at The Truman Annex in Key West
- Bedrooms:
- 5
- 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 $940 per night (USD)VRBO
- From $720 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $720 per night (USD)Expedia
- From $736 per night (USD)
VRBO
AQUA BREEZE at 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 $736 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $381 per night (USD)
VRBO
SHADY NOOK at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $381 per night (USD)VRBO
- From $239 per night (USD)
Expedia
A PALM TREE PARADISE @ the Key West Golf Club
- Bedrooms:
- 2
- 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 $239 per night (USD)Expedia
- From $403 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $403 per night (USD)VRBO
- From $733 per night (USD)
Expedia
THE PLANTATION at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $733 per night (USD)Expedia
- From $995 per night (USD)
VRBO
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 $995 per night (USD)VRBO
- From $526 per night (USD)
Expedia
LIFE IN THE SLOW LANE at the Truman Annex in Key West
- Bedrooms:
- 3
- 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 $526 per night (USD)Expedia
- From $720 per night (USD)
VRBO
SALTWATER ANGLER at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $720 per night (USD)VRBO
- From $369 per night (USD)
Expedia
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 $369 per night (USD)Expedia
- From $710 per night (USD)
VRBO
A HARBOUR ROOST at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $710 per night (USD)VRBO
- From $362 per night (USD)
Expedia
A SANCTUARY HOME at the Key West Golf Club
- Bedrooms:
- 3
- 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 $362 per night (USD)Expedia
- From $376 per night (USD)
VRBO
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 $376 per night (USD)VRBO
- From $502 per night (USD)
Expedia
ASCENSION at The Truman Annex in Key West
- 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 $502 per night (USD)Expedia
- From $460 per night (USD)
VRBO
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 $460 per night (USD)VRBO
- 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 PricingVRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $728 per night (USD)
Expedia
OCEAN BREEZE at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $728 per night (USD)Expedia
- From $477 per night (USD)
VRBO
SAGO PALM at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $477 per night (USD)VRBO
- From $394 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 $394 per night (USD)Expedia
- From $368 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 3
- 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 $368 per night (USD)VRBO
- From $350 per night (USD)
Expedia
The Bolivar, Old Town Key West Monthly vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tuck upstairs in the back of a historic Conch house is a home away from home with private back porch. 1 Block walk from ...
From $350 per night (USD)Expedia