
Key West National Wildlife Refuge Rentals

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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
- From $677 per night (USD)
Expedia
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 $677 per night (USD)Expedia
- From $457 per night (USD)
VRBO
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 $457 per night (USD)VRBO
- From $436 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 $436 per night (USD)Expedia
- From $410 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 $410 per night (USD)VRBO
- From $817 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 $817 per night (USD)Expedia
- From $470 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 $470 per night (USD)VRBO
- From $3810 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 $3810 per night (USD)Expedia
- From $249 per night (USD)
VRBO
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 $249 per night (USD)VRBO
- From $1931 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 $1931 per night (USD)VRBO
- From $848 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 $848 per night (USD)VRBO
- From $418 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 $418 per night (USD)Expedia
- From $635 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 $635 per night (USD)VRBO
- From $390 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 $390 per night (USD)Expedia
- From $222 per night (USD)
VRBO
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 $222 per night (USD)VRBO
- From $357 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Gulf Getaway | Condo w/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $233 per night (USD)VRBO
- From $691 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $691 per night (USD)Expedia
- From $962 per night (USD)
VRBO
Washer & Dryer, Near Downtown - The Mesa House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $962 per night (USD)VRBO
- From $794 per night (USD)
Expedia
Casa Rosa: 4BR/4BA house, pool, near Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $794 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $450 per night (USD)VRBO
- From $251 per night (USD)
Expedia
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You have many ...
From $251 per night (USD)Expedia
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VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For PricingVRBO
- From $601 per night (USD)
Expedia
Balcony & Near Downtown - Cloud Suite on Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of w ...
From $601 per night (USD)Expedia
- From $393 per night (USD)
VRBO
A PEACE OF PARADISE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $393 per night (USD)VRBO
- From $417 per night (USD)
Expedia
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $417 per night (USD)Expedia
- From $266 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $266 per night (USD)VRBO
- From $371 per night (USD)
Expedia
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)Expedia
- From $307 per night (USD)
VRBO
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $307 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Keys to Paradise - Shipyard Truman Annex - LOWEST RATES JUNE-SEPTEMBER!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $339 per night (USD)Expedia
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Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
Click For PricingExpedia
- From $283 per night (USD)
Expedia
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W/D
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $283 per night (USD)Expedia
- From $476 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR/3.5BA Condo & Pool + LAST KEY SERVI
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $476 per night (USD)VRBO
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Expedia
Southern Skies, Stylish Home in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
Click For PricingExpedia
- From $470 per night (USD)
VRBO
Key West Sunset Serenade - w Pool & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The first time you arrive to Key West everything indicates that you’ve reached the last tropical island along the ribbon ...
From $470 per night (USD)VRBO
- From $357 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)Expedia
- From $178 per night (USD)
VRBO
Monkey House by AvantStay | Pool, by Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $178 per night (USD)VRBO
- From $787 per night (USD)
Expedia
Rooftop Penthouse, Walk to Duval - KAMP
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $787 per night (USD)Expedia
- From $451 per night (USD)
VRBO
Gorgeous Bahama Village 4Bd 4Ba all ensuite, 2x parking, pets, ideal location!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, ...
From $451 per night (USD)VRBO
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Expedia
Studio Unit in quiet resort adjacent to Old Town Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For PricingExpedia
- From $459 per night (USD)
VRBO
**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICES…
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE COZY STAR ...
From $459 per night (USD)VRBO
- From $1158 per night (USD)
Expedia
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1158 per night (USD)Expedia
- From $818 per night (USD)
VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $818 per night (USD)VRBO
- From $505 per night (USD)
Expedia
Royal Palm in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of changing licensing ...
From $505 per night (USD)Expedia
- From $528 per night (USD)
VRBO
Pool, Pet Friendly, & Near Duval - Coastal Rose
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $528 per night (USD)VRBO
- From $454 per night (USD)
Expedia
Pet Friendly, Near Duval - Rose Petal Petite Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $454 per night (USD)Expedia
- From $820 per night (USD)
VRBO
Pet Friendly, & Near Duval - Rose Key Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $820 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Tropical Cottage w/ Private Pool--Two blocks from Duval - Near Hemingway House!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $184 per night (USD)Expedia
- From $945 per night (USD)
VRBO
An Ocean Serenity in Truman Annex, Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award ...
From $945 per night (USD)VRBO
- From $2664 per night (USD)
Expedia
Pool & Parking, & Near Duval - The Rigby House
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $2664 per night (USD)Expedia
- From $697 per night (USD)
VRBO
NEW!!! Gorgeous! Beacon Terrace in the Truman Annex Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
"Beacon Terrace" in the Truman Annex is a beautifully renovated town home in the historic Foundry in the Truman Annex. ...
From $697 per night (USD)VRBO
- From $973 per night (USD)
VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $973 per night (USD)VRBO
- From $657 per night (USD)
VRBO
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $657 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Elegant Boutique Room w/ Private Patio & Garden - Duval Street steps away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $465 per night (USD)VRBO
- From $874 per night (USD)
VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $874 per night (USD)VRBO
- From $467 per night (USD)
Expedia
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $467 per night (USD)Expedia
- From $484 per night (USD)
VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $484 per night (USD)VRBO
- From $456 per night (USD)
VRBO
Stylish Boutique Room w/ 2 Queen Beds - Access Pool & Poolside Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $456 per night (USD)VRBO
- From $226 per night (USD)
VRBO
Cozy on Caroline - Key West Seaport
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $226 per night (USD)VRBO
- From $345 per night (USD)
Expedia
Southern Skies, Stylish Home in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart of Key West's His ...
From $345 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Charming 1923 2 Bedroom, 1 Bath home with bonus loft.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to The Emma House! A delightful 1923 Key West retreat located in the heart of historic and vibrant Bahama Villa ...
From $216 per night (USD)VRBO
- From $1125 per night (USD)
Expedia
Hyatt Sunset Harbor Resort Timeshare available 2 weeks only Mar22-Apr5, 2026
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coveted Hyatt Resort unit available for 2 consecutive weeks - located in between Truman Annex, Duval St. and Mallory Sq ...
From $1125 per night (USD)Expedia
- From $713 per night (USD)
VRBO
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbe ...
From $713 per night (USD)VRBO
- From $370 per night (USD)
Expedia
Jerry's Escape - Truman @ Duval | Cozy Studio Perfect for Couples
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Truman @ Duval - Unit C | Cozy Studio Perfect for Couples Experience your perfect romantic retreat, offering a charming ...
From $370 per night (USD)Expedia
- From $436 per night (USD)
VRBO
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime Location Welcome to your perfect family getaway in the ...
From $436 per night (USD)VRBO
- From $483 per night (USD)
VRBO
Charming Hideaway with Pool – Walk to Duval St & Local Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $483 per night (USD)VRBO
- From $467 per night (USD)
VRBO
Sunny Florida Escape with Pool, Beach Access & Stunning Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $467 per night (USD)VRBO
- From $585 per night (USD)
Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $585 per night (USD)Expedia
- From $778 per night (USD)
VRBO
The Penthouse at Custom House Inn | New! Coastal Escape on Duval Street!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Penthouse at Custom House Inn | Serene Coastal Escape on Duval Street! Immerse yourself in the calm and comfort of ...
From $778 per night (USD)VRBO
- Click For Pricing
Expedia
Most Beautiful View on Key West?
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make yourself at home in this 2-bedroom Key West retreat. This cool condo features a beautiful view from every room. Spa ...
Click For PricingExpedia
- From $739 per night (USD)
VRBO
Upscale 2-bedroom villa in the heart of Old Town. Minutes to Duval & Mallory Sq
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this upscale condo in Key West. This terrific property features 2 bedrooms with 1 king bed and 1 queen bed, a ...
From $739 per night (USD)VRBO
- From $537 per night (USD)
Expedia
Sandbar Suite | 2 bed/2 bath apartment with patio overlooking Front Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Sandbar Suite – 2BR/2BA Island Getaway with Front Street views Welcome to The Sandbar Suite, a bright and breezy 2- ...
From $537 per night (USD)Expedia
- From $606 per night (USD)
VRBO
KEY WEST- Amazing 3 rd floor corner unit overlooking Florida Bay and Yacht Club.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Consider this 3rd floor corner condo overlooking the Florida Bay and Yacht Club as your next vacation destination. Enjoy ...
From $606 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Casa Mamisa - 2 bedroom home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The two bedroom Casa Mamisa is your home away from home on a quiet lane just off of Duval Street. This peaceful space fe ...
From $422 per night (USD)Expedia
- From $136 per night (USD)
VRBO
Sunny Island Escape | 1 bed, 1 bath monthly rental in heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the Heart of Key West from This Charming Monthly Vacation Retreat Stay just steps from the action in this be ...
From $136 per night (USD)VRBO
- From $587 per night (USD)
VRBO
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman Annex Welcome to your sunny esc ...
From $587 per night (USD)VRBO
- From $1824 per night (USD)
VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1824 per night (USD)VRBO
- From $968 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $968 per night (USD)VRBO
- From $2236 per night (USD)
VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
- From $1941 per night (USD)
VRBO
The Banyan | Concierge | Beach Access | Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1941 per night (USD)VRBO
- From $11524 per night (USD)
VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $11524 per night (USD)VRBO
- From $2236 per night (USD)
VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
- From $1839 per night (USD)
VRBO
Galleon | Marina | Lux Resort | Pool | Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1839 per night (USD)VRBO
- From $1839 per night (USD)
VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $1839 per night (USD)VRBO
- From $5625 per night (USD)
VRBO
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
- From $5625 per night (USD)
VRBO
Key West Florida Charming 1-bedroom resort with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
- From $5625 per night (USD)
VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
- From $1227 per night (USD)
VRBO
No secrets at Pilar's Secret - Just a great location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1227 per night (USD)VRBO
- From $812 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $812 per night (USD)VRBO
- From $1609 per night (USD)
Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1609 per night (USD)Expedia
- From $3478 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $3478 per night (USD)VRBO
- From $1189 per night (USD)
VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1189 per night (USD)VRBO
- From $1705 per night (USD)
VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1705 per night (USD)VRBO
- From $1308 per night (USD)
VRBO
Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1308 per night (USD)VRBO
- From $470 per night (USD)
VRBO
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $470 per night (USD)VRBO
- From $354 per night (USD)
Expedia
SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $354 per night (USD)Expedia
- From $410 per night (USD)
VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $410 per night (USD)VRBO
- From $642 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $642 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $385 per night (USD)VRBO
- From $534 per night (USD)
Expedia
\"Tranquility \" At Ann Street Gardens Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $534 per night (USD)Expedia