Key West National Wildlife Refuge Rentals
From $430 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 $430 per night (USD)VRBO
From $1725 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 $1725 per night (USD)VRBO
From $1117 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 $1117 per night (USD)VRBO
From $898 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 $898 per night (USD)VRBO
From $393 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 $393 per night (USD)VRBO
From $1473 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 $1473 per night (USD)Expedia
From $208 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 $208 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 $667 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 $667 per night (USD)VRBO
From $1996 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 $1996 per night (USD)Expedia
From $578 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 $578 per night (USD)VRBO
From $849 per night (USD)VRBO
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 ...
From $849 per night (USD)VRBO
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 $483 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 $483 per night (USD)VRBO
From $516 per night (USD)VRBO
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 $516 per night (USD)VRBO
From $311 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 $311 per night (USD)VRBO
From $650 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 $650 per night (USD)VRBO
From $658 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 $658 per night (USD)VRBO
From $1190 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 $1190 per night (USD)VRBO
From $875 per night (USD)Expedia
**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 $875 per night (USD)Expedia
From $711 per night (USD)VRBO
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 ...
From $711 per night (USD)VRBO
From $365 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 $365 per night (USD)VRBO
From $278 per night (USD)VRBO
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)VRBO
From $410 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 $410 per night (USD)VRBO
From $512 per night (USD)VRBO
MAI TAI TERRACE - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Mai Tai Terrace – Your Tropical Getaway in Key West Located in The Shipyard subdivision of the sought-after ...
From $512 per night (USD)VRBO
From $362 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 $362 per night (USD)VRBO
From $578 per night (USD)VRBO
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 $578 per night (USD)VRBO
From $659 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 $659 per night (USD)VRBO
From $1060 per night (USD)VRBO
**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 $1060 per night (USD)VRBO
From $321 per night (USD)Expedia
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 $321 per night (USD)Expedia
From $606 per night (USD)VRBO
Truman Annex Best Location in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature ...
From $606 per night (USD)VRBO
From $731 per night (USD)Expedia
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 $731 per night (USD)Expedia
From $1591 per night (USD)VRBO
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 $1591 per night (USD)VRBO
From $443 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 $443 per night (USD)VRBO
From $650 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 $650 per night (USD)VRBO
From $603 per night (USD)VRBO
Miami Vice Sailboat Used For TV Series we moved out of the Perry Marina
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
We are working on renovations other repairs. We are taking a limited number of day sails and plan to retire. Please chec ...
From $603 per night (USD)VRBO
From $511 per night (USD)VRBO
**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 $511 per night (USD)VRBO
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 $345 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 $345 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $833 per night (USD)VRBO
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 $833 per night (USD)VRBO
From $585 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 $585 per night (USD)VRBO
From $1296 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 $1296 per night (USD)VRBO
From $487 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 $487 per night (USD)VRBO
From $1551 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 $1551 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 $384 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 $384 per night (USD)VRBO
From $727 per night (USD)Expedia
~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 $727 per night (USD)Expedia
From $777 per night (USD)VRBO
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 $777 per night (USD)VRBO
From $634 per night (USD)Expedia
Fantastic Fall Special Rates.
- 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 $634 per night (USD)Expedia
From $1057 per night (USD)VRBO
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 $1057 per night (USD)VRBO
From $593 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 $593 per night (USD)VRBO
From $1020 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 $1020 per night (USD)VRBO
From $610 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! Will be retiring and will take limited number of custom sailing trips. Located ...
From $610 per night (USD)VRBO
From $516 per night (USD)VRBO
**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 $516 per night (USD)VRBO
From $1119 per night (USD)Expedia
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 $1119 per night (USD)Expedia
From $1218 per night (USD)VRBO
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 $1218 per night (USD)VRBO
From $534 per night (USD)Expedia
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)Expedia
From $516 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 $516 per night (USD)VRBO
From $904 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 $904 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 $550 per night (USD)Expedia
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 $550 per night (USD)Expedia
From $340 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 $340 per night (USD)VRBO
From $590 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 $590 per night (USD)VRBO
From $2281 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 $2281 per night (USD)VRBO
From $447 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 $447 per night (USD)VRBO
From $1386 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 $1386 per night (USD)VRBO
From $1107 per night (USD)Expedia
**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 $1107 per night (USD)Expedia
From $524 per night (USD)VRBO
**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 $524 per night (USD)VRBO
From $1850 per night (USD)Expedia
**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 $1850 per night (USD)Expedia
From $1023 per night (USD)VRBO
**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 $1023 per night (USD)VRBO
From $1342 per night (USD)Expedia
**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 $1342 per night (USD)Expedia
From $2524 per night (USD)VRBO
**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 $2524 per night (USD)VRBO
Click For PricingExpedia
Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 21-Dec 28.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is the luxury boutique resort you and your family and friends deserve. A few steps to famous Mallory Square and all ...
Click For PricingExpedia
From $580 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 $580 per night (USD)VRBO
From $381 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 $381 per night (USD)Expedia
From $1925 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 $1925 per night (USD)VRBO
From $1032 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 $1032 per night (USD)Expedia
From $586 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 $586 per night (USD)VRBO
From $574 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 $574 per night (USD)Expedia
From $754 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 $754 per night (USD)VRBO
From $416 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 $416 per night (USD)Expedia
From $1681 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 $1681 per night (USD)VRBO
From $1294 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 $1294 per night (USD)Expedia
From $1404 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 $1404 per night (USD)VRBO
From $955 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 $955 per night (USD)Expedia
From $433 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 $433 per night (USD)VRBO
From $672 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 $672 per night (USD)Expedia
From $283 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 $283 per night (USD)VRBO
From $357 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 $357 per night (USD)Expedia
From $546 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 $546 per night (USD)VRBO
From $182 per night (USD)VRBO
June & August 2026 now available! 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 $182 per night (USD)VRBO
From $994 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 $994 per night (USD)VRBO
From $404 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 $404 per night (USD)VRBO
From $594 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 $594 per night (USD)VRBO
From $952 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 $952 per night (USD)VRBO
From $1000 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 $1000 per night (USD)VRBO
Click For PricingExpedia
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For PricingExpedia
From $416 per night (USD)VRBO
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $416 per night (USD)VRBO
From $463 per night (USD)Expedia
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $463 per night (USD)Expedia