
Key West National Wildlife Refuge Rentals

- 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
- Click For Pricing
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 ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $758 per night (USD)
VRBO
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 $758 per night (USD)VRBO
- From $429 per night (USD)
Expedia
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 $429 per night (USD)Expedia
- From $480 per night (USD)
VRBO
**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 $480 per night (USD)VRBO
- From $351 per night (USD)
Expedia
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 $351 per night (USD)Expedia
- From $2137 per night (USD)
VRBO
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2137 per night (USD)VRBO
- From $317 per night (USD)
Expedia
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 $317 per night (USD)Expedia
- From $564 per night (USD)
VRBO
\"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 $564 per night (USD)VRBO
- From $749 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $749 per night (USD)VRBO
- From $339 per night (USD)
VRBO
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)VRBO
- From $431 per night (USD)
Expedia
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 $431 per night (USD)Expedia
- From $725 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 $725 per night (USD)VRBO
- From $638 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 $638 per night (USD)VRBO
- From $418 per night (USD)
VRBO
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)VRBO
- From $576 per night (USD)
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 ...
From $576 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 $291 per night (USD)
VRBO
See you in Sept SALE 37%off price shownVilla /close to everything/off st prking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
READ ADDITIONAL REVIEWS -Old Town -Whitehead St- BEST LOCATION -On Whitehead St. -Steps to Duval -Any discounts offered ...
From $291 per night (USD)VRBO
- 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 $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 $401 per night (USD)
VRBO
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
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 $401 per night (USD)VRBO
- From $308 per night (USD)
Expedia
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)Expedia
- From $498 per night (USD)
VRBO
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)VRBO
- From $479 per night (USD)
Expedia
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)Expedia
- From $1098 per night (USD)
VRBO
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)VRBO
- From $505 per night (USD)
Expedia
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)Expedia
- 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
- 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 $716 per night (USD)
VRBO
Beautiful ocean view condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A luxury, ocean front, 2 bedroom, (king in master, twins or twins as king in guest bedroom, queen sleeper in living room ...
From $716 per night (USD)VRBO
- From $1355 per night (USD)
Expedia
A Palm Tree Haven in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1355 per night (USD)Expedia
- From $2301 per night (USD)
VRBO
Harbor House Suite A | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $2301 per night (USD)VRBO
- From $792 per night (USD)
Expedia
World's End at Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy spectacular 3-way Key West views from the large wrap-around deck without leaving your rental unit. This 2 bedroom ...
From $792 per night (USD)Expedia
- From $598 per night (USD)
VRBO
Ann Street Tranquility: A cozy and peaceful cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $598 per night (USD)VRBO
- Click For Pricing
Expedia
Hyatt Residence Club, Sunset Harbor - Beautiful Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the heart of Old Town, perfectly situated on the western side of the island, this gracious retreat overlooks the Gulf ...
Click For PricingExpedia
- From $541 per night (USD)
VRBO
Old Town Key West Cottage 3bed/2bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Fully furnished ground floor cottage with 3 bedrooms (queen bed in every bedroom), 2 full bathrooms, plus a loft with an ...
From $541 per night (USD)VRBO
- Click For Pricing
Expedia
Best Location -Hyatt Sunset Harbor- water view-Jan 26 to Feb 2. Seven nights
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
LISTING is ONLY available January 26 to Feb 2. Best location in town. Only 1.5 blocks to Duvall Street but quiet. Key We ...
Click For PricingExpedia
- From $641 per night (USD)
VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $641 per night (USD)VRBO
- From $886 per night (USD)
VRBO
SEAPORT SUMMIT at Galleon Resort-Beach-Pool-King Suite-BBQ-near Mallory Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
GALLEON RESORT LUXURY WATERFRONT PENTHOUSE with LOFT + GREAT VIEWS OF THE MARINA, OCEAN & HISTORIC SEAPORT 5th FLOOR M ...
From $886 per night (USD)VRBO
- From $1933 per night (USD)
VRBO
Luxury 4BDR/4BA Penthouse | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Luxury Harbor House Suites! We proudly offer you a newly renovated 2,400SF, 4BDR/4BA Penthouse in the Cit ...
From $1933 per night (USD)VRBO
- Click For Pricing
Expedia
Priced to book! 2 Bdr/2Ba Walking distance to Duval St., Mallory Square, Trolley
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For PricingExpedia
- Click For Pricing
VRBO
DOWNTOWN KEY WEST 2BED OCEANFRONT!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtow ...
Click For PricingVRBO
- From $1043 per night (USD)
Expedia
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)Expedia
- From $1578 per night (USD)
VRBO
Conch House in Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Quintessential Grand Key West Estate! The James J. Curtis House c. 1874 was acquired by the Navy in 1903 and the home b ...
From $1578 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Cubana Casita in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cubana Casita is an easy-access ground floor condo with one bedroom and 1 baths. This special home's 'from the ground up ...
From $165 per night (USD)Expedia
- From $841 per night (USD)
VRBO
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)VRBO
- From $361 per night (USD)
Expedia
Another Siesta at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Find the best of Key West at your doorstep with this beautiful one-bedroom condo, with a private patio, a shared swimmin ...
From $361 per night (USD)Expedia
- From $468 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
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 $468 per night (USD)VRBO
- From $531 per night (USD)
Expedia
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + 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! There’s no do ...
From $531 per night (USD)Expedia
- From $481 per night (USD)
VRBO
A Fish Bowl at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Fish Bowl has been completely remodeled with attention to detail. A beautiful 1 bedroom, 1 bath downstairs condo locat ...
From $481 per night (USD)VRBO
- From $724 per night (USD)
Expedia
Private Island Oasis Getaway, A Dream Vacation
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Imagine the ultimate Key West dream home that feels like a faraway oasis - a short ferry ride to Sunset Key will have yo ...
From $724 per night (USD)Expedia
- From $816 per night (USD)
VRBO
Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...
From $816 per night (USD)VRBO
- From $528 per night (USD)
Expedia
SUMMER SAVINGS!!!! \nLatitude Adjustment @ Truman Annex Shipyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Latitude Adjustment located in the Truman Annex Shipyard just steps from beaches, restaurants & bars, Key We ...
From $528 per night (USD)Expedia
- From $983 per night (USD)
VRBO
Tropical Oasis in the Truman Annex with a private pool\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Searching for the perfect vacation home away from it all? Your hunt ends in here! A Wave from it All is a recently remod ...
From $983 per night (USD)VRBO
- From $198 per night (USD)
Expedia
THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!
- 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 $198 per night (USD)Expedia
- Click For Pricing
VRBO
Sunset Harbor Beach Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hyatt Sunset Harbor Resort is located in Key West, 2,300 feet from Mallory Square. Key West Aquarium is 2,650 feet from ...
Click For PricingVRBO
- From $427 per night (USD)
Expedia
Beachy Keen @ the Truman Annex
- 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 co ...
From $427 per night (USD)Expedia
- From $397 per night (USD)
VRBO
HELLO GORGEOUS! - Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
HELLO GORGEOUS! Welcome to this stunning Conch Cottage style home that has all the bells and whistles that you have be ...
From $397 per night (USD)VRBO
- From $422 per night (USD)
Expedia
A SALTWATER REMEDY ~ 2 BR/2.5 Ba Townhome Truman Annex w/ Shared Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PERFECT CAREFREE RETREAT... Located in the small private community of Porter Court within Truman Annex and set around a ...
From $422 per night (USD)Expedia
- 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
- 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
- Click For Pricing
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 ...
Click For PricingVRBO
- From $745 per night (USD)
Expedia
**THE PIRATE’S PENTHOUSE @ BAHAMA VILLAGE** 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! Located acros ...
From $745 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 $1969 per night (USD)
Expedia
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)Expedia
- From $686 per night (USD)
VRBO
**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)VRBO
- From $527 per night (USD)
Expedia
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)Expedia
- From $249 per night (USD)
VRBO
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)VRBO
- From $1035 per night (USD)
Expedia
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)Expedia
- From $278 per night (USD)
VRBO
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 $278 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 $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 $872 per night (USD)
VRBO
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $872 per night (USD)VRBO
- 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 $472 per night (USD)
Expedia
**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 $472 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $417 per night (USD)
Expedia
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)Expedia
- From $327 per night (USD)
VRBO
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)VRBO
- From $432 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 $432 per night (USD)VRBO
- From $375 per night (USD)
VRBO
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 $375 per night (USD)VRBO
- From $647 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 $647 per night (USD)Expedia
- From $181 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 $181 per night (USD)VRBO
- From $359 per night (USD)
Expedia
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 $359 per night (USD)Expedia
- From $499 per night (USD)
VRBO
New Years special in gorgeous Bahama Village 4Bd 4.5 Ba all ensuite, 2x parking!
- 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 $499 per night (USD)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
- From $1001 per night (USD)
VRBO
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 $1001 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $621 per night (USD)
VRBO
**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)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
- From $683 per night (USD)
VRBO
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)VRBO
- From $175 per night (USD)
Expedia
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)Expedia