Key West National Wildlife Refuge, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Key West National Wildlife Refuge, Florida on RentalSaver.com!

Key West National Wildlife Refuge Rentals

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SEAPORT SKYLINE-Beach-Pool-King-BBQ-Hot Tub-Rooftop views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OCEANFRONT CASUAL LUXURY CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. PENTHOUSE COND ...
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VRBO
From $247 per night (USD)
Expedia
Caroline On My Mind-New Listing-Light, Bright and Airy!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $247 per night (USD)
Expedia
From $648 per night (USD)
VRBO
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This prope ...
From $648 per night (USD)
VRBO
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Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
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Expedia
$SUMMER RATES STARTING AT 200 PER NIGHT!!! \nMAI TAI TERRACE - KEY WEST$
From $317 per night (USD)
VRBO
SUMMER RATES STARTING AT 200 PER NIGHT!!! \nMAI TAI TERRACE - KEY WEST
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Mai Tai Terrace located in The Shipyard subdivision of Truman Annex in beautiful Key West. This 2-bedroom, ...
From $317 per night (USD)
VRBO
From $674 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $674 per night (USD)
VRBO
From $294 per night (USD)
VRBO
Blue Bayou: Ideal Key West Location W/ Shared Pool, Steps from Beach, Duval Street & Mallory Square!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, with no exceptions. Please review additiona ...
From $294 per night (USD)
VRBO
From $311 per night (USD)
Expedia
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latitudes Restaurant!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Homeowners' Association (HOA) mandates a minimum rental period of 30 nights, and no exceptions can be made. Please revie ...
From $311 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Historic house near Duval Street
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This private home is located on a secluded lane just behind the Key West Lighthouse across from the Hemingway Home Museu ...
From $439 per night (USD)
VRBO
From $1554 per night (USD)
Expedia
**ELEGANT ESCAPE @ THE ANNEX** Lavish Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! There’s no be ...
From $1554 per night (USD)
Expedia
$Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16$
From $900 per night (USD)
VRBO
Two-bedroom townhouse overlooking the harbor.\n \nONLY AVAILABLE Nov. 9 - Nov 16
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Two story townhouse with two bedrooms, pull out couch, full kitchen, three bathrooms. Overlooking the harbor with full ...
From $900 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Lavender Jungle by AvantStay | Great Location w/ Patio & Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $324 per night (USD)
Expedia
From $682 per night (USD)
VRBO
Truman's Hideaway by AvantStay | Great Location w/ Patio, Outdoor Dining & BBQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $682 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Conch Adventure by AvantStay | Great Location w/ Patio, Outdoor Dining
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $356 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Sundown Refuge by AvantStay | Great Location w/ Outdoor Dining & Shared Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $495 per night (USD)
VRBO
From $427 per night (USD)
Expedia
Linger Longer by AvantStay | Key West Walkable | Gated Community, Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $427 per night (USD)
Expedia
From $200 per night (USD)
VRBO
La Casita by AvantStay | Steps to Duval Street | Month Long Stays Only
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* The location of La Casita cannot be beaten -- right ...
From $200 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $406 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Emma's Secret by AvantStay | Heart of Old Town | Month Long Stays Only
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Located in one of Key West’s historic and most cult ...
From $173 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Easy Livin' by AvantStay | Key West Home w/ Pool & BBQ | Week Long Stays Only
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $820 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Parrot Perch by AvantStay | Old Town Key West w/ Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $429 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Artist Garden by AvantStay | Great Location w/ Balcony, Shared Pool & BBQ!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $456 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Key West Found by AvantStay | Close to Shops w/ Patio & Shared Pool! |
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $543 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Bahamian Reed by AvantStay | Walk to Everything! w/ Community Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $392 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Serenity by AvantStay | Guest House in Old Town w/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Located in Bahama Village, a quaint neighborhood in ...
From $258 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Pool, 2 Blocks to Duval St, Gated Community | Shipyard Treasure by AvantStay
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $352 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Always Your Paradise by AvantStay | Shared Pool | Near Zachary Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $330 per night (USD)
VRBO
From $645 per night (USD)
Expedia
Key West Casa by AvantStay | Communal Pool | BBQ & Patio | Near Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $645 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Breezy Bungalow by AvantStay | Close 2 Zachary Taylor State Park & Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $414 per night (USD)
VRBO
From $948 per night (USD)
Expedia
Southard Getaway by AvantStay | w/ Covered Patio, Great Location & Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $948 per night (USD)
Expedia
From $504 per night (USD)
VRBO
Beach House Condo by AvantStay | Communal Pool, Gated Community | Great Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $504 per night (USD)
VRBO
From $475 per night (USD)
Expedia
A Place In Paradise by AvantStay | Key West Walkable w/ Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $475 per night (USD)
Expedia
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VRBO
Priced to book! Sleeps 4- Walking Distance to Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
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VRBO
From $841 per night (USD)
Expedia
Amelia Home by AvantStay | In Historic Old Town w/ Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper o ...
From $841 per night (USD)
Expedia
From $1043 per night (USD)
VRBO
Three Condos w/ Entertainment, Private Parking & Beach Nearby - Great for Groups
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1043 per night (USD)
VRBO
From $793 per night (USD)
Expedia
Noah's Retreat in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of changing licensing ...
From $793 per night (USD)
Expedia
From $462 per night (USD)
VRBO
A Fish Bowl Too at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cozy two bedroom condo in Key West is the perfect place for a romantic getaway or a solo retreat. As you enter the ...
From $462 per night (USD)
VRBO
From $984 per night (USD)
Expedia
SEAPORT SAILING-Beach-Pool-King-BBQ-Hot Tub-Race Week!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OCEANFRONT CASUAL LUXURY MARINA PENTHOUSE CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO ...
From $984 per night (USD)
Expedia
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VRBO
Priced to Book! 1BR/1BA Walking distance to Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
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VRBO
From $686 per night (USD)
Expedia
**TRUMAN’S TROVE @ THE ANNEX** Private Home & 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! Hunting for t ...
From $686 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Banana Key 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 $527 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Shipyard in Key West, FL
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of changing licensing ...
From $249 per night (USD)
Expedia
From $1035 per night (USD)
VRBO
Kemp House in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of ...
From $1035 per night (USD)
VRBO
From $365 per night (USD)
Expedia
AHOY MATE! New Shipyard Listing!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly updated condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled w ...
From $365 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Old Town Key West Luxury 4BR – Private Pool by Historic Seaport - Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $476 per night (USD)
VRBO
From $418 per night (USD)
Expedia
ISLE BE BACK at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Thank you for considering Isle Be Back for your escape to the tropical paradise of Key West. Here you will enjoy the lap ...
From $418 per night (USD)
Expedia
From $308 per night (USD)
VRBO
The Courtyard in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can ...
From $308 per night (USD)
VRBO
From $498 per night (USD)
Expedia
Havana Hideaway 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 $498 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Campbell Suite in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell S ...
From $479 per night (USD)
VRBO
From $1098 per night (USD)
Expedia
A Wave From It All at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Searching for the perfect vacation home away from it all? Your hunt ends in here! A Wave from it All is an updated and t ...
From $1098 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 2 full bathroom {q ...
From $505 per night (USD)
VRBO
From $255 per night (USD)
VRBO
Duval Sq., Old Town, very walkable, full kitchen, pool, parking, 2 BR/2.5 BA.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 Bedrooms 2.5 Bathrooms. Comfortably Sleeps 4, Max occupancy 6. 1240 total sq. ft. Bedroom nr. 1: 1 King bed, with a b ...
From $255 per night (USD)
VRBO
$\A Captain's Quarters at the Truman Annex in Key West\$
From $1070 per night (USD)
VRBO
\"A Captain's Quarters at the Truman Annex in Key West\"
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Searching for the perfect vacation home away from it all? Your hunt ends in here! A Captain's Quarters is an updated and ...
From $1070 per night (USD)
VRBO
From $334 per night (USD)
Expedia
A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 ...
From $334 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Shipyard 208-6 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 $417 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Bahama Village studio @ the Galleria!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This studio has been lovingly renovated and is a wonderful space in historic Old Town to enjoy all of Key West! The unit ...
From $327 per night (USD)
Expedia
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VRBO
Experience The Galleon – A 5-Star Timeshare Resort in Charming Old Key West, Fl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon, in the heart of "Old Town Key West" located on the historic Seaport/Marina and a short walk to world famous ...
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VRBO
From $621 per night (USD)
Expedia
**HARBORSIDE HARMONY @ TRUMAN ANNEX** Waterfront Condo + 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! HARBORSIDE HA ...
From $621 per night (USD)
Expedia
From $405 per night (USD)
VRBO
J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to J Ferrara #9, your ideal retreat in the heart of Key West! Nestled on a quiet street in the artist-inspired ...
From $405 per night (USD)
VRBO
From $751 per night (USD)
Expedia
The Perch on Duval- Hip & Modern Duval Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Perch on Duval, an elegant and charming 2-bedroom vacation rental situated in the heart of downtown Key West. ...
From $751 per night (USD)
Expedia
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VRBO
Key West Sunset Harbor - Mallory Square only steps away - Walk to downtown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Hyatt Vacation Club - 2bed 2 bath - View of the water. Walk to Mallory Square, Parking for 1 vehicle, Free Wifi and Pool ...
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VRBO
From $885 per night (USD)
Expedia
Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Admirals Gold, a luxurious weekly vacation rental nestled in the prestigious Truman Annex neighborhood. This ...
From $885 per night (USD)
Expedia
$Charming, newly renovated Key West home\n2 bed, 1 bath with bonus loft bedroom$
From $310 per night (USD)
VRBO
Charming, newly renovated Key West home\n2 bed, 1 bath with bonus loft bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our charming home nestled in the heart of Key West's historic Bahama Village in Old Town! This quaint and inv ...
From $310 per night (USD)
VRBO
From $683 per night (USD)
Expedia
Truman Annex end-unit home, private outdoor spaces, pool, close to Duval & beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There's a lot to love about #1 at the Foundry! It's nestled within Key's West world-famous Truman Annex where you'll fin ...
From $683 per night (USD)
Expedia
From $175 per night (USD)
VRBO
One Bedroom Cottage House in Old Town Key West by the Hemingway House.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
🌴 Escape to Your Private Key West Cottage Retreat! 🌞 Welcome to your charming and secluded Key West cottage, a perfec ...
From $175 per night (USD)
VRBO
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Expedia
OLD TOWN LUXURY HOME - completely remodeled, updated, steps to Duval Street.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in the heart of Old Town, this rare home has 3 Bedrooms with 3.5 Baths in the Main House. New in 2021 to the hig ...
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Expedia
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VRBO
Beautiful Studio over looking the Key West Marine at Sunset Harbor
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Walk out of your room and walk down to the pool over looking the Harbor. you can watch the sunset from the pool. You are ...
Click For Pricing
VRBO
From $520 per night (USD)
VRBO
Traditional Two Queen, Pier House, Comfortable Ambiance, next to Nightlife Sight
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 $520 per night (USD)
VRBO
From $759 per night (USD)
VRBO
Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Family friendly, secluded retreat within Key West Truman Annex gated community. Our lanai is a destination in of itself ...
From $759 per night (USD)
VRBO
From $337 per night (USD)
Expedia
Ann Street Gardens in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $337 per night (USD)
Expedia
Click For Pricing
VRBO
Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer/dryer pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the beauty of Key West from this 2-bedroom 2 bath resort. The spacious bedrooms feature a king and queen bed, p ...
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VRBO
From $514 per night (USD)
Expedia
**CASA AVILA @ OLD TOWN** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! CASA AVILA co ...
From $514 per night (USD)
Expedia
From $556 per night (USD)
VRBO
Walk to Duval Street - Iconic Mermaid House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to an iconic Key West paradise with this exceptional vacation rental, where a mermaid theme enchants throughout t ...
From $556 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to 1015 Eaton Street, nestled in the heart of the Historic Seaport neighborhood. Renovated in 2024, this 4-bedro ...
From $788 per night (USD)
Expedia
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Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 6, Swimming Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
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Expedia
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Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 4, Swimming Pool, Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 2, Swimming Pool, Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
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VRBO
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Expedia
Sailor’s Sanctuary | Stunning Updated Condo Near Duval Street!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sailor’s Sanctuary | Stunning Updated Condo Near Duval Street! Welcome to Sailor’s Sanctuary, a beautifully renovated g ...
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Expedia
From $583 per night (USD)
VRBO
Key West Hyatt Sunset Harbor Villa - Thanksgiving week! 11/23 - 30, 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Key West Sunset Harbor Villa boasts 2 bedrooms, including a beautiful master suite with jacuzzi tub and full shower ...
From $583 per night (USD)
VRBO
From $607 per night (USD)
Expedia
COCONUT COTTAGE- Island Vibes & Cozy Stays W/ Pool & Parking - OLD TOWN KEY WEST
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Coconut Cottage a stunning new construction home in Old Town Key West's Bahama Village. Featuring 2-bedroom, ...
From $607 per night (USD)
Expedia
From $257 per night (USD)
VRBO
1-bedroom 2 blocks to Duval, close to beach, parking, and pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located in Key West 2 blocks from Duval and half a mile to Beach, enjoy what this 1-bedroom condo has to offer. This lov ...
From $257 per night (USD)
VRBO
$\An Island Retreat in the Truman Annex, Key West\$
From $766 per night (USD)
Expedia
\"An Island Retreat in the Truman Annex, Key West\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This charming two bedroom, two and one half bath town home has recently been updated and added to our rental program! Fr ...
From $766 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Poolside Palms in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summer Discounts!Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of c ...
From $230 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Dee's Dream Sunset Condo with WiFi and AC in Key West - 2 bdrm - Shipyard #151
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This beautiful 2-bedroom condo in the quiet and private gated Shipyard Community. It has rave reviews & 2 blocks from fa ...
From $523 per night (USD)
VRBO
From $691 per night (USD)
VRBO
**GRENN TURTLE COTTAGE @ THE ANNEX** Stunning Private Home + 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! GREEN TURTLE ...
From $691 per night (USD)
VRBO
From $246 per night (USD)
Expedia
A SEAGLASS PARADISE. ~ Charming 2 BR/1 Ba Condo in Truman Annex!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $246 per night (USD)
Expedia
From $571 per night (USD)
VRBO
**HEMINGWAY'S HAVEN @ OLD TOWN** Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Nestled in th ...
From $571 per night (USD)
VRBO
From $468 per night (USD)
VRBO
A Caribbean Alternative townhome in Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Caribbean Alternative is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West ...
From $468 per night (USD)
VRBO
From $1664 per night (USD)
VRBO
Galleon Resort, Pool, Hot Tub, In Town, Pool, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios h ...
From $1664 per night (USD)
VRBO
From $1669 per night (USD)
VRBO
Banyon Resort, Beach, Pool, Hot Tub, In Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In the heart of historic Old Town Key West, The Banyan Resort boasts a storied history and sits on a historic, mid-1800' ...
From $1669 per night (USD)
VRBO
From $674 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $674 per night (USD)
VRBO
From $219 per night (USD)
Expedia
THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $219 per night (USD)
Expedia
From $786 per night (USD)
VRBO
3 Bedroom Key West Home - Perfect Location & Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street, hund ...
From $786 per night (USD)
VRBO
From $180 per night (USD)
VRBO
STUNNING! HEART OF OLD TOWN!: Walk to Duval and Historic Seaport in minutes.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Live like a local in this unique loft apartment in the heart of Key West's Old Town historic district. Walk to Duval Str ...
From $180 per night (USD)
VRBO
$\Paradise Found\ in Historic Key West$
From $378 per night (USD)
VRBO
\"Paradise Found\" in Historic Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Paradise has been Found at this beautiful Old Town Key West condo! Just steps away from the new Truman Waterfront, Fort ...
From $378 per night (USD)
VRBO
From $851 per night (USD)
Expedia
A Buccaneer Bay at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Searching for the perfect vacation home away from it all? Your hunt ends in Key West! Discover BUCCANEER BAY, a tasteful ...
From $851 per night (USD)
Expedia
From $967 per night (USD)
VRBO
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Inspired by romantic turn-of-the-century architecture, Bella Grand Premier Estate is a unique Old Town Key West estate w ...
From $967 per night (USD)
VRBO
From $1895 per night (USD)
Expedia
Key West Island Rendezvous - Private Compound Steps Off Duval w/Pool - Sleeps 12
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in t ...
From $1895 per night (USD)
Expedia
From $1969 per night (USD)
VRBO
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
The iconic William Skelton Home in downtown Key West offers an ideal retreat for your group of 16 guests. The six bedroo ...
From $1969 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Key Lime Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Weekly Treat!! A whole downtown vacation experience for the entire family. Rent this condo in the hearth of most request ...
From $528 per night (USD)
VRBO

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