Key West Rentals
From $413 per night (USD)VRBO
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)VRBO
From $2946 per night (USD)Expedia
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 $2946 per night (USD)Expedia
From $412 per night (USD)VRBO
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 $412 per night (USD)VRBO
From $579 per night (USD)Expedia
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 $579 per night (USD)Expedia
From $353 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 $353 per night (USD)VRBO
From $402 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 $402 per night (USD)Expedia
From $444 per night (USD)VRBO
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 $444 per night (USD)VRBO
From $340 per night (USD)Expedia
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 $340 per night (USD)Expedia
From $290 per night (USD)VRBO
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 $290 per night (USD)VRBO
From $391 per night (USD)Expedia
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 $391 per night (USD)Expedia
From $835 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 $835 per night (USD)VRBO
From $546 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 $546 per night (USD)Expedia
From $411 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 $411 per night (USD)VRBO
From $376 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 $376 per night (USD)Expedia
From $665 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 $665 per night (USD)VRBO
From $445 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 $445 per night (USD)Expedia
From $1429 per night (USD)VRBO
Villa Déjà vu Key West - 4BR Private Villa in Old Town Key West with Heated Pool sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get ...
From $1429 per night (USD)VRBO
From $664 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 $664 per night (USD)Expedia
From $730 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 $730 per night (USD)VRBO
From $705 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 $705 per night (USD)Expedia
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 $668 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 $668 per night (USD)Expedia
From $450 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 $450 per night (USD)VRBO
From $228 per night (USD)Expedia
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 $228 per night (USD)Expedia
From $406 per night (USD)VRBO
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)VRBO
From $1283 per night (USD)Expedia
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 $1283 per night (USD)Expedia
From $778 per night (USD)VRBO
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 $778 per night (USD)VRBO
From $395 per night (USD)Expedia
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SALT AIR & SUNSHINE... This 1 bedroom, 1 bathroom private single family home is a sweet surprise just off Duval St. It's ...
From $395 per night (USD)Expedia
From $1233 per night (USD)VRBO
TROPICAL RETREAT ~ 3 Bedroom/3.5 Bath 1/2 Block from Duval w/ Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
SPOIL YOURSELF IN PARADISE... Indulge yourself in the rustic charm of historic Key West enveloped in lush, vibrant surro ...
From $1233 per night (USD)VRBO
From $507 per night (USD)Expedia
**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 $507 per night (USD)Expedia
From $255 per night (USD)VRBO
INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w/ Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
YOUR PEACEFUL PARADISE AWAITS… Find this unmatched island escape tucked away in the lust and intimate Southernmost Caban ...
From $255 per night (USD)VRBO
From $465 per night (USD)Expedia
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w/ Pool & Compact Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home ...
From $465 per night (USD)Expedia
From $506 per night (USD)VRBO
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 $506 per night (USD)VRBO
From $1812 per night (USD)Expedia
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1812 per night (USD)Expedia
From $1304 per night (USD)VRBO
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
YOUR SOUTHERN SANCTUARY... Find your serenity in this stylish and cheery townhome, just a short distance away from the s ...
From $1304 per night (USD)VRBO
From $577 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 $577 per night (USD)Expedia
From $181 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 $181 per night (USD)VRBO
From $558 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 $558 per night (USD)Expedia
From $576 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 $576 per night (USD)VRBO
From $957 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 $957 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 $406 per night (USD)VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $406 per night (USD)VRBO
Click For PricingVRBO
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 $246 per night (USD)Expedia
Anchors Away - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Away – Classic Conch Style Living in Old Town Key West Experience the charm of traditional Key West living at A ...
From $246 per night (USD)Expedia
From $525 per night (USD)VRBO
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
UNMATCHED ISLAND RETREAT… Tucked away within one of the island’s most impressive lanes in the Casa Marina district, this ...
From $525 per night (USD)VRBO
From $753 per night (USD)Expedia
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 $753 per night (USD)Expedia
From $233 per night (USD)VRBO
**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a quiet residential street in the beautiful key west neighborhood of casa marina just blocks from Higgs Beach ...
From $233 per night (USD)VRBO
From $533 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 $533 per night (USD)Expedia
From $265 per night (USD)VRBO
Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sophisticated 2 bedroom, 1 bathroom Key West Home just steps from the white sand and salty hues of Smathers Beach, short ...
From $265 per night (USD)VRBO
From $380 per night (USD)Expedia
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 $380 per night (USD)Expedia
From $479 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 $479 per night (USD)VRBO
From $1451 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 $1451 per night (USD)Expedia
From $378 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 $378 per night (USD)VRBO
From $422 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 $422 per night (USD)Expedia
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $512 per night (USD)Expedia
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $512 per night (USD)Expedia
From $195 per night (USD)VRBO
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 $195 per night (USD)VRBO
From $633 per night (USD)Expedia
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FAR FROM ORDINARY... Extraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak i ...
From $633 per night (USD)Expedia
From $347 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 $347 per night (USD)VRBO
From $593 per night (USD)VRBO
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $593 per night (USD)VRBO
From $870 per night (USD)VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space ...
From $870 per night (USD)VRBO
From $480 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 $480 per night (USD)Expedia
From $1589 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 $1589 per night (USD)VRBO
From $488 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 $488 per night (USD)Expedia
From $679 per night (USD)VRBO
Old Town 4 /4.5 house with private pool and 2 poolside cottages + outdoor shower
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Newly restored Key West property in old town. Blocks from Duval and the harbor. Private heated pool central AC washer dr ...
From $679 per night (USD)VRBO
From $497 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 $497 per night (USD)Expedia
From $447 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 $447 per night (USD)VRBO
From $378 per night (USD)VRBO
Key West Private Home/Pool/on the Water\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
LOCATION LOCATION! Located on the only canal in Key West, with a protected bird sanctuary across the canal. A short Ub ...
From $378 per night (USD)VRBO
From $606 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 $606 per night (USD)VRBO
From $894 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 $894 per night (USD)Expedia
From $174 per night (USD)VRBO
Home away from home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the gated community of the Key West Golf Club, enjoy your morning coffee in the enclosed back porch overlooki ...
From $174 per night (USD)VRBO
From $488 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 $488 per night (USD)Expedia
From $613 per night (USD)VRBO
Charming 3 bedroom blocks from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Conch Style home on Southard street is just a few blocks from Duval St and across from the old Harris Scho ...
From $613 per night (USD)VRBO
From $599 per night (USD)Expedia
Luxury two floor apartment in prime location of famous Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This Modern & Spacious 2 story Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Sho ...
From $599 per night (USD)Expedia
From $466 per night (USD)VRBO
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 $466 per night (USD)VRBO
From $437 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $437 per night (USD)VRBO
From $932 per night (USD)VRBO
**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 $932 per night (USD)VRBO
From $248 per night (USD)Expedia
ALMOST HEAVEN ~ Stunning 2 Bedroom, 2 Bathroom Condo with Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE: This community is currently undergoing balcony repair property-wide potentially through April 2026. A ...
From $248 per night (USD)Expedia
From $318 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $318 per night (USD)VRBO
From $1217 per night (USD)Expedia
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 $1217 per night (USD)Expedia
From $564 per night (USD)VRBO
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 $564 per night (USD)VRBO
From $267 per night (USD)Expedia
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)Expedia
From $453 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 $453 per night (USD)VRBO
From $347 per night (USD)VRBO
CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Description: Welcome to Corazon, a stunning 2-bedroom vacation rental in the heart of Key West's Old Town neighborhood. ...
From $347 per night (USD)VRBO
From $3802 per night (USD)VRBO
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 $3802 per night (USD)VRBO
From $1028 per night (USD)Expedia
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 $1028 per night (USD)Expedia
From $1267 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1267 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 $1354 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 $1354 per night (USD)VRBO
From $176 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 $176 per night (USD)Expedia
From $2074 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 $2074 per night (USD)VRBO
From $2916 per night (USD)Expedia
Classic Key West Estate - 7BR Mansion off Duval St w/Pool & Guesthouse Sleeps 16
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation re ...
From $2916 per night (USD)Expedia
From $1814 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 $1814 per night (USD)VRBO
From $328 per night (USD)Expedia
SEA-NIC VIEW ~ 2 BR/2Ba Water-front views, Heated Pool Access and Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
IT'S A SWELL LIFE… Endless island treasures engulf this oceanfront haven which is your one stop destination for a comple ...
From $328 per night (USD)Expedia
From $1136 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 $1136 per night (USD)VRBO
From $878 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 $878 per night (USD)Expedia
From $862 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 $862 per night (USD)VRBO
From $475 per night (USD)Expedia
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 $475 per night (USD)Expedia
From $482 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 $482 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