
Key West National Wildlife Refuge Rentals

- From $446 per night (USD)
VRBO
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Fam ...
From $446 per night (USD)VRBO
- From $1083 per night (USD)
VRBO
Rare Penthouse 2 bed/2bath additional King in loft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $1083 per night (USD)VRBO
- From $771 per night (USD)
VRBO
The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!
- 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 $771 per night (USD)VRBO
- From $772 per night (USD)
VRBO
Rose Lane Villas - Villa Vista - 2 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 $772 per night (USD)VRBO
- From $311 per night (USD)
VRBO
Villa Fleur at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and d ...
From $311 per night (USD)VRBO
- From $1310 per night (USD)
Expedia
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
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 $1310 per night (USD)Expedia
- From $246 per night (USD)
VRBO
Private Home in Heart of Old Town (Shared Pool!)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $246 per night (USD)VRBO
- From $435 per night (USD)
Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $435 per night (USD)Expedia
- From $623 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside Condo & 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! OLD TOWN OASI ...
From $623 per night (USD)VRBO
- From $1751 per night (USD)
Expedia
Key West Suites Hotel - Adam Scott Rote Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...
From $1751 per night (USD)Expedia
- From $449 per night (USD)
VRBO
Key West Rooster
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please call or text if you’d like to book our home 702 232... 3750 When booking our home please include a brief descri ...
From $449 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $467 per night (USD)
VRBO
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 $467 per night (USD)VRBO
- From $475 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $475 per night (USD)Expedia
- From $534 per night (USD)
VRBO
A Touch of Bermuda at Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping ...
From $534 per night (USD)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 $287 per night (USD)
VRBO
Villa Nomade at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. Th ...
From $287 per night (USD)VRBO
- From $736 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 $736 per night (USD)VRBO
- From $419 per night (USD)
VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $419 per night (USD)VRBO
- From $648 per night (USD)
Expedia
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)Expedia
- From $884 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! While Old Tow ...
From $884 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $623 per night (USD)
VRBO
Treasure Cove- 2BDR/2.5BA | 2 Bed, 2.5 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $623 per night (USD)VRBO
- From $330 per night (USD)
Expedia
Villa Mer at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The li ...
From $330 per night (USD)Expedia
- From $341 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $341 per night (USD)VRBO
- From $278 per night (USD)
Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $278 per night (USD)Expedia
- From $418 per night (USD)
VRBO
A Touch Of Cuba In Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and sin ...
From $418 per night (USD)VRBO
- From $317 per night (USD)
Expedia
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)Expedia
- From $344 per night (USD)
VRBO
Freshly Renovated Cottage Old Town MONTHLY
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This freshly renovated cottage in the the heart of Old Key West is located only 2 blocks off Duval St and is a short wal ...
From $344 per night (USD)VRBO
- From $461 per night (USD)
Expedia
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $461 per night (USD)Expedia
- From $439 per night (USD)
VRBO
Rose Lane Villas - Villa Rosa - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 wit ...
From $439 per night (USD)VRBO
- From $993 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush 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! Hidden amongs ...
From $993 per night (USD)Expedia
- From $289 per night (USD)
VRBO
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has t ...
From $289 per night (USD)VRBO
- From $443 per night (USD)
VRBO
Truman Annex Best Location in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature ...
From $443 per night (USD)VRBO
- From $593 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $593 per night (USD)VRBO
- From $1980 per night (USD)
Expedia
Balcony - Sky Suites Retreat, on Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $1980 per night (USD)Expedia
- From $421 per night (USD)
VRBO
Old Town Beauty built in 1883
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy the lovely Key West ocean breeze from your private Tree House. This is the quietest area of Old Town but only4 blo ...
From $421 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 $602 per night (USD)
VRBO
Miami Vice Sailboat Used For TV Series with 2 Hour Sandbar Motor Boat Trip
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
We are working on renovations other fall.text us to get more details ! Come see us this fall or wi yet at another marina ...
From $602 per night (USD)VRBO
- From $341 per night (USD)
Expedia
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & 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! It is not so ...
From $341 per night (USD)Expedia
- From $1156 per night (USD)
VRBO
Waterfront Views from Dolphin Watch
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than tw ...
From $1156 per night (USD)VRBO
- From $461 per night (USD)
VRBO
Location, Location, Location!!! Downtown Key West - Truman Annex!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
All the amenities of a fantastic resort suite and free assigned parking in the middle of everything in Key West...2/1 th ...
From $461 per night (USD)VRBO
- From $433 per night (USD)
VRBO
Sunset views at the Galleon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
From $433 per night (USD)VRBO
- From $706 per night (USD)
Expedia
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $706 per night (USD)Expedia
- From $518 per night (USD)
VRBO
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $518 per night (USD)VRBO
- From $1039 per night (USD)
VRBO
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
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 $1039 per night (USD)VRBO
- From $378 per night (USD)
VRBO
Large Floorplan & Yard, Sunny 2BR KING/twin, 1 Bath, Truman Annx, Grd Flr, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amazing LOCATION! Truman Annex: SHABBY CHICKEN - come stay at the large & proud bird in town!! Large front yard and po ...
From $378 per night (USD)VRBO
- From $1413 per night (USD)
VRBO
Palm Trees Ocean Breeze Key West FL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck over ...
From $1413 per night (USD)VRBO
- From $321 per night (USD)
VRBO
Truman Annex - Beautiful Townhome - President's Lane
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2-story townhouse; master bedroom with King Bed and double doors to deck; full bath; second bedroom with two t ...
From $321 per night (USD)VRBO
- From $307 per night (USD)
VRBO
Tranquil 2-BR Condo in Truman Annex, Steps to Pool & 5-Min Walk to Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our lovely condo which is located in the famed Truman Annex Complex right in the heart of fabulous Key West. ...
From $307 per night (USD)VRBO
- From $704 per night (USD)
VRBO
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 ni ...
From $704 per night (USD)VRBO
- From $525 per night (USD)
Expedia
Beautiful sunsets!! Harbour Place, Truman Annex. Walk or bike to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Harbor Place is one of the most prestigious properties in Key West! This unit offers breath taking water views overlook ...
From $525 per night (USD)Expedia
- From $475 per night (USD)
VRBO
SUMMER ISN'T OVER YET - PROCES REDUCED FOR OPEN NIGHTS!!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $475 per night (USD)VRBO
- From $985 per night (USD)
Expedia
Historic Old Town Key West - Turtle House, Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $985 per night (USD)Expedia
- From $449 per night (USD)
VRBO
Key West Hen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Give me a call if you have any questions! 702-232-3750 ****The roof has been replaced and the gutters are being done as ...
From $449 per night (USD)VRBO
- From $846 per night (USD)
VRBO
Tropical State of Mind Key West FL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in ...
From $846 per night (USD)VRBO
- From $528 per night (USD)
VRBO
Key West 44ft Sailboat Wild Thing-we are moving !
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We are moving ! Check for details here! Send a note Plan for your getaway soon for specials like sand bar trip on a mot ...
From $528 per night (USD)VRBO
- From $526 per night (USD)
Expedia
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $526 per night (USD)Expedia
- From $838 per night (USD)
VRBO
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $838 per night (USD)VRBO
- From $914 per night (USD)
Expedia
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both ...
From $914 per night (USD)Expedia
- From $534 per night (USD)
VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $534 per night (USD)VRBO
- From $429 per night (USD)
VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 wit ...
From $429 per night (USD)VRBO
- From $844 per night (USD)
VRBO
Hyatt Sunset Harbour Resort-Prime location on Key West!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All rentals will be in seven-night increments with a Friday through Sunday for check-in. Thank you for choosing Dash R ...
From $844 per night (USD)VRBO
- From $343 per night (USD)
VRBO
Cozy Piece of Key West History
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECTLY located, 100 y-o "Conch" House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, compl ...
From $343 per night (USD)VRBO
- From $303 per night (USD)
VRBO
THE OLD SAPODILLA HOUSE ~ Pet Friendly Home in Historic Bahama Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $303 per night (USD)VRBO
- From $372 per night (USD)
VRBO
~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $372 per night (USD)VRBO
- From $468 per night (USD)
VRBO
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 n ...
From $468 per night (USD)VRBO
- From $1382 per night (USD)
VRBO
~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. ...
From $1382 per night (USD)VRBO
- From $482 per night (USD)
VRBO
~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Home is available September 1 for a monthly rental (only). 28 night minimum** WEEKLY RENTAL: This property has a 7 n ...
From $482 per night (USD)VRBO
- From $1238 per night (USD)
VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...
From $1238 per night (USD)VRBO
- From $1014 per night (USD)
VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $1014 per night (USD)VRBO
- From $539 per night (USD)
Expedia
**VILLA BAHAMA @ THE ANNEX** Villa 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! VILLA BAHAMA ...
From $539 per night (USD)Expedia
- From $2651 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $2651 per night (USD)VRBO
- From $1461 per night (USD)
Expedia
**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval & Beach + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BAHAMIAN BAMB ...
From $1461 per night (USD)Expedia
- From $655 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $655 per night (USD)VRBO
- From $2515 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $2515 per night (USD)Expedia
- From $571 per night (USD)
VRBO
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + 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! SALTWATER HAR ...
From $571 per night (USD)VRBO
- From $449 per night (USD)
Expedia
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + 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! LA PETITE PEN ...
From $449 per night (USD)Expedia
- From $1734 per night (USD)
VRBO
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $1734 per night (USD)VRBO
- From $863 per night (USD)
Expedia
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Traveling wit ...
From $863 per night (USD)Expedia
- From $575 per night (USD)
VRBO
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & 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! If you dream ...
From $575 per night (USD)VRBO
- From $543 per night (USD)
Expedia
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & 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! SEA CAPTAIN'S ...
From $543 per night (USD)Expedia
- From $730 per night (USD)
VRBO
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + 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! This Old Town ...
From $730 per night (USD)VRBO
- From $382 per night (USD)
Expedia
Truman Annex Gem • 2BR Condo • Walk to Beach & Bars
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 Guests Welcome to Innis-free, ou ...
From $382 per night (USD)Expedia
- From $1770 per night (USD)
VRBO
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $1770 per night (USD)VRBO
- From $1785 per night (USD)
Expedia
**DIAMOND GIRL @ THE ANNEX** Elegant 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! Seals & Croft ...
From $1785 per night (USD)Expedia
- From $1202 per night (USD)
VRBO
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $1202 per night (USD)VRBO
- From $873 per night (USD)
Expedia
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $873 per night (USD)Expedia
- From $430 per night (USD)
VRBO
Truman Annex, two blocks from Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Available for weekly, or longer, rentals (monthly or longer starting in 2026) this three-story townhouse is located on a ...
From $430 per night (USD)VRBO
- From $556 per night (USD)
Expedia
**SOUTHERNMOST PALMS @ THE ANNEX** Villa 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! When you thin ...
From $556 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $265 per night (USD)VRBO
- From $411 per night (USD)
Expedia
Cheery Beach Getaway Near Local Attractions - Pool & Easy Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Perch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $411 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Elegant home with with patio & community pool - walk to beaches & Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Mangrove Lagoon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $385 per night (USD)VRBO
- From $187 per night (USD)
VRBO
2026 now available! SPARKLING Old Town PRIVATE 3BR Lagoon Pool& FIVE stars!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This colorful three bedroom, two full bath, private, and historic home is a wonderful spot to vacation, live like a loca ...
From $187 per night (USD)VRBO
- From $571 per night (USD)
VRBO
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This modern O ...
From $571 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, 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 $185 per night (USD)VRBO
- From $341 per night (USD)
VRBO
Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ pool
- Bedrooms:
- 1
- 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 $341 per night (USD)VRBO
- From $323 per night (USD)
VRBO
Truman Annex unit 254
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $323 per night (USD)VRBO
- From $819 per night (USD)
VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $819 per night (USD)VRBO
- From $993 per night (USD)
VRBO
Hyatt Sunset Harbor Resort for ONLY Sunday to Sunday Week's stay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is for A WEEK'S Stay Only in a 2 Bedroom 2 Bathroom Villa for 6 People. Discover this relaxing oasis in the heart ...
From $993 per night (USD)VRBO