Key West Rentals
From $250 per night (USD)HomeAway
A tastefully decorated space in the heart of Old Town Key West
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $250 per night (USD)HomeAway
From $232 per night (USD)VRBO
~ MARGARET TRUMAN SUITE ~ Updated Suite w/ Shared Pool In Perfect Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: The Margaret Truman Suite is steps from Duval Street, the Lighthouse, Southernmost Point, the Hemi ...
From $232 per night (USD)VRBO
From $550 per night (USD)HomeAway
The Dolphin House by AT HOME IN KEY WEST
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the ...
From $550 per night (USD)HomeAway
From $259 per night (USD)VRBO
PET FRIENDLY! 3 Bedroom 3 bathroom home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
"FlipFlop Inn" is a beautiful 3 Bedroom 3 Bath home(each bedroom has its own private full bath), located in the luxu ...
From $259 per night (USD)VRBO
From $325 per night (USD)HomeAway
Sunshine Dream- Monthly Rental the first of the month to the end of the month.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunshine Dreams is a historic conch cottage located on a quiet lane in the center of Old Town. This one bedroom, one bat ...
From $325 per night (USD)HomeAway
From $250 per night (USD)VRBO
Key West Found by AT HOME IN KEY WEST
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Just steps away from Harry Truman's "Little White House" you’ll find your vacation dreams come true! Located in the his ...
From $250 per night (USD)VRBO
From $250 per night (USD)HomeAway
Tropical Paradise-Pool- Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax poolside on a private deck, enjoying the bougainvillaea draped over the masonry privacy fence. Banana trees and m ...
From $250 per night (USD)HomeAway
From $300 per night (USD)VRBO
Starfish Monthly Rental 2 blocks from Duval street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious 2 bedroom, 2 bath shotgun style home is your ideal Key West Vacation Home away from home. Walk down the hu ...
From $300 per night (USD)VRBO
From $125 per night (USD)HomeAway
Direct Ocean View from Your Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom ...
From $125 per night (USD)HomeAway
From $250 per night (USD)VRBO
"Coconut Cabana" Old Town Tropical Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An Old town Key West home, located in the Historic District and just one half a block off of world famous Duval Street. ...
From $250 per night (USD)VRBO
From $165 per night (USD)HomeAway
Colony Sunset- Bright and airy cottage in the heart of old town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retrea ...
From $165 per night (USD)HomeAway
From $700 per night (USD)VRBO
Classic Key West Estate ~ Spectacular Historic Seaport Home
- Bedrooms:
- 6.5
- Bathrooms:
- 7
- Sleeps:
- 14
Featured on the HGTV House Hunter's on Vacation series in July 2011, the timeless charm of this distinguished Classic Ke ...
From $700 per night (USD)VRBO
From $325 per night (USD)HomeAway
Featured on HGTV***MULTIPLE MONTH DISCOUNT***Updated 3/3 Pool Home with 1/1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive t ...
From $325 per night (USD)HomeAway
From $292 per night (USD)VRBO
Secluded, Private, Tropical Retreat In Old Town, Key West.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 story cypress cottage on National Historic Register. 2 bedrooms (queen) upstairs sharing bathroom. Additional bathro ...
From $292 per night (USD)VRBO
From $185 per night (USD)HomeAway
Shipyard Treasure by AT HOME IN KEY WEST
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Finding a perfect property for your family vacation is easier said than done, but this contemporary condo at Truman Anne ...
From $185 per night (USD)HomeAway
From $240 per night (USD)VRBO
~ STEAMPLANT 208 ~ Luxurious Condo w/ Breathtaking Views & Rooftop Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Welcome to Steamplant 208! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $150 per night (USD)HomeAway
Sea Biscuit 1/2 block to Duval, private pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sea Biscuit – Completely renovated in 2011. I do weekly rentals SAT. to SAT from November 1 until May . 8 people max in ...
From $150 per night (USD)HomeAway
From $160 per night (USD)VRBO
Comfortable Key West Family Home. Free Parking and WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated commun ...
From $160 per night (USD)VRBO
From $98 per night (USD)HomeAway
Peaceful townhome, located in the Key West Golf Club with 2 community pools
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Clu ...
From $98 per night (USD)HomeAway
From $300 per night (USD)VRBO
The Mermaids House - Old Town, MONTHLY ! Historic Bahama Conch House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of the Old Town Historic district of Bahama Village Key West, where life in the old days was very differen ...
From $300 per night (USD)VRBO
From $142 per night (USD)HomeAway
~ SOLARIS GARDEN ~ Enjoy Old Town Livin' Just A Short Walk to All the Action!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About THE PROPERTY: Solaris Garden, located on one of Key West most private slow lanes, and is a Bohemian Dream! Perfe ...
From $142 per night (USD)HomeAway
From $450 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. Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant ...
From $450 per night (USD)VRBO
From $180 per night (USD)HomeAway
Beach House Condo by AT HOME IN KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home. A beautiful 2 bedr ...
From $180 per night (USD)HomeAway
From $225 per night (USD)VRBO
A Place In Paradise by AT HOME IN KEY WEST
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! You will experience true Key West liv ...
From $225 per night (USD)VRBO
From $450 per night (USD)HomeAway
Charming gated community just off Duval, Monthly Rental Only
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Esperanza Suite is a professionally managed, pet friendly, bi-level suite available on a monthly basis. It has a very ...
From $450 per night (USD)HomeAway
From $600 per night (USD)VRBO
Flirty Flamingo Key West
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $600 per night (USD)VRBO
From $550 per night (USD)HomeAway
Easy Livin' by AT HOME IN KEY WEST
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you ...
From $550 per night (USD)HomeAway
From $100 per night (USD)VRBO
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $100 per night (USD)VRBO
From $100 per night (USD)HomeAway
McCartney's Manor- Luxury Private Cottage, Courtyard and Hot Tub!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Part of 4 exclusive units at Abbey Road, McCartney's Manor is in a private, gated compound. The state-of-the-art kitche ...
From $100 per night (USD)HomeAway
From $70 per night (USD)VRBO
Heart of Old Town, Truman Annex Private END UNIT 2BR king/twin, Grnd FL, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
TRUMAN ANNEX: The ROOSTER RETREAT is a lovely 2 bedroom, (1 king/2 twins, and queen bed) 1 newly remodeled bathroom. We ...
From $70 per night (USD)VRBO
From $100 per night (USD)HomeAway
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 $100 per night (USD)HomeAway
From $300 per night (USD)VRBO
Award Winning Home Next to Lighthouse! Newly Updated Private Pool, Gated Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This licensed vacation home was recently featured on Key West's 2017 historic home tour and is available to rent monthly ...
From $300 per night (USD)VRBO
From $70 per night (USD)HomeAway
The Galleria~Unit #11 Located in Historic Bahama Village! Bikes Included!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleria #11 – A Hidden Gem on Howe Street! small and no frills but affordable for Key West! Good things DO ...
From $70 per night (USD)HomeAway
From $150 per night (USD)VRBO
Oceanfront Island Dreams, Storybook Sunsets & Fantastic Views in Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Overlooking the Atlantic Ocean on your private porch with fridge bar type mirrored walls with sail fish of glass. Many ...
From $150 per night (USD)VRBO
From $129 per night (USD)HomeAway
Newton Street Hideaway: A secluded one bedroom
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
28 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town ...
From $129 per night (USD)HomeAway
From $275 per night (USD)VRBO
Abbey Road-Great for large group-Shared Pools-1/2 block from Duval Street!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Abbey Road - Gated Compound, Sleeps up to 12! Daily Housekeeping! Including Lennon's Lodge (Sleeps 6 with 8 person hot ...
From $275 per night (USD)VRBO
From $195 per night (USD)HomeAway
Southard Getaway - Truly Paradise by AT HOME IN KEY WEST
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Im ...
From $195 per night (USD)HomeAway
From $375 per night (USD)VRBO
Mango Cottage- 2BR/2BA Family-Friendly Old Town Private Home with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mango Cottage This recently-restored historic Conch house is an excellent vacation home. The kitchen and bathrooms have ...
From $375 per night (USD)VRBO
From $200 per night (USD)HomeAway
Oceanfront with free WIFI, PAPAYA PLACE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean! This gr ...
From $200 per night (USD)HomeAway
From $189 per night (USD)VRBO
"A Touch of Paradise" 2 bedrm, 2 FULL baths, pool, Great LOCATION!!!read reviews
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Best Location!!Rare 2 FULL baths! This Key West Getaway, with beachy decor, Great Pool...is so close to all the local Ke ...
From $189 per night (USD)VRBO
From $100 per night (USD)HomeAway
Harrison's Hideaway - Cottage, Pvt. Spa - 2 Shared Pools - Steps from Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Part of 4 exclusive units at Abbey Road, this free standing historic Cigar Maker's cottage is at 918-920 Center Street. ...
From $100 per night (USD)HomeAway
From $350 per night (USD)VRBO
Retreat In The Heart Of Old Town Key West (Monthly Rental Only)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Harmony Sol is the perfect spot for your Key West getaway. Located in the middle of Old Town Key West and within walk di ...
From $350 per night (USD)VRBO
From $250 per night (USD)HomeAway
Casa De Cuba a Beach House - Cuban Flair Steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location! Style! Elegance! This restored "beach" home is fabulous combination of everything a great vacation property sh ...
From $250 per night (USD)HomeAway
From $118 per night (USD)VRBO
SUITE CAROLINE - Luxury condo within steps to Key West's historic seaport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
28 DAY MINIMUM RENTAL Situated in the heart of Old Town Key West, on the legendary Caroline Street, this beautifully res ...
From $118 per night (USD)VRBO
From $523 per night (USD)HomeAway
Tucked away near the Southernmost Point, Louisa's Hideaway is it!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. ...
From $523 per night (USD)HomeAway
From $250 per night (USD)VRBO
Beach Club #104 - Unique oceanfront living with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $250 per night (USD)VRBO
From $525 per night (USD)HomeAway
Duval Square Penthouse: A gorgeous condo on Duval St with room for everyone
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
Freshly renovated in January 2019– and ready for you! Duval Square Penthouse has enough luxurious square footage for ...
From $525 per night (USD)HomeAway
From $232 per night (USD)VRBO
~ HARRY TRUMAN SUITE ~ Updated Suite w/ Heated Pool Just Steps to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: The Harry Truman Suite is steps from Duval Street, the Lighthouse, Southernmost Point, the Hemingwa ...
From $232 per night (USD)VRBO
From $161 per night (USD)HomeAway
Monthly Rental in the Heart of Old Town
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM Open the door to this brand new home in the very center of Old Town Key West, and begin your perfect ex ...
From $161 per night (USD)HomeAway
From $35 per night (USD)VRBO
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $35 per night (USD)VRBO
From $200 per night (USD)HomeAway
~ LITTLE MISS MAGIC ~ Lovely Home w/ Sparkling Pool In PERFECT Location
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: "Little Miss Magic" lies in an absolutely perfect Key West location! Relax in the midst of a calm ...
From $200 per night (USD)HomeAway
From $400 per night (USD)VRBO
Luxury Galleon Resort & Marina 2 Bed/2 Bath Marina View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
From $400 per night (USD)VRBO
From $250 per night (USD)HomeAway
Family House- Two K bedrooms, 1.5 baths, Pvt.Spa in Garden Setting-Shared Pools!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 6
This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/ ...
From $250 per night (USD)HomeAway
From $425 per night (USD)VRBO
Pete's Cottages: Twin Cypress cottages steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $425 per night (USD)VRBO
From $182 per night (USD)HomeAway
New Listing! - Mid Town Getaway with pool & jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-styl ...
From $182 per night (USD)HomeAway
From $125 per night (USD)VRBO
Stay at our tropical oasis in the Historic District close to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully remodeled Cottage in the Historic District of Key West. Walk or ride your bike to anywhere on the island. ...
From $125 per night (USD)VRBO
From $190 per night (USD)HomeAway
Located right by Smathers Beach, 4 PALMS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West is all about the beach and the ocean and this tastefully decorated rental located right on Smather's Beach migh ...
From $190 per night (USD)HomeAway
From $234 per night (USD)VRBO
Key West: 3 BR, 2 BA Luxury Yacht; Special Now!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Upscale 'Keys Yacht Vacation'! 3 bedroom, 2 bath beautiful yacht. Currently located in one of the nicest marinas in all ...
From $234 per night (USD)VRBO
From $240 per night (USD)HomeAway
Leeward Isle Key West Retreat: 2 BR / 2 BA townhouse in Key West, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Leeward Isle Key West Retreat – Location is everything! A hidden gem in the heart of Old Town Key West. Nestled in a q ...
From $240 per night (USD)HomeAway
From $118 per night (USD)VRBO
~ CASABLANCA TOO ~ Cute Cottage w/ Private Hot Tub & Off Street Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About THE PROPERTY: Casablanca Too is the perfect get-a-way vacation rental for two! Casablanca Too is one half of a ...
From $118 per night (USD)VRBO
From $75 per night (USD)HomeAway
Harbour Place 115 in Truman Annex Key West
- Bedrooms:
- 3.5
- 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 $75 per night (USD)HomeAway
From $500 per night (USD)VRBO
Parrothead's Golf Paradise with Private Pool in Sanctuary
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your tropical townhome overlooking the 18th fairway complete with private jetted pool. Gated community "The S ...
From $500 per night (USD)VRBO
From $375 per night (USD)HomeAway
Penthouse on Duval Street ~ Perfectly staged on Duval Street Key West
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly staged in the island’s city center, this spectacular downtown Key West rental received a major upscale renovat ...
From $375 per night (USD)HomeAway
From $742 per night (USD)VRBO
~ GRAND MAISON ~ Amazing Home On Duval w/ Heated Pool & Off Street Parking
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point ...
From $742 per night (USD)VRBO
From $180 per night (USD)HomeAway
Linger Longer by AT HOME IN KEY WEST
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation! Enjoy a ...
From $180 per night (USD)HomeAway
From $185 per night (USD)VRBO
The Hollinsed House - Harvey's Haven - Great Location!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Harvey's Haven - beauty and economy in the heart of Old Town Key West! Ideally located at 611 Southard Street ...
From $185 per night (USD)VRBO
From $185 per night (USD)HomeAway
Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located only two miles from Duval 1800 Atlantic Blvd offers the best of both worlds; close to downtown without most of t ...
From $185 per night (USD)HomeAway
From $489 per night (USD)VRBO
David and Christopher Welcome You To Gracie's Place
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
David and Christopher have been together 24 years, moved to Key West in 2013, recently added Gracie's Place to the prope ...
From $489 per night (USD)VRBO
From $1009 per night (USD)HomeAway
Family Reunion - Pool Garden Compound
- Bedrooms:
- 10
- Bathrooms:
- 12
- Sleeps:
- 24
Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key Wes ...
From $1009 per night (USD)HomeAway
From $260 per night (USD)VRBO
La Casa del Luces- Steps from the Beach and Duval - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
La Casa de Luces - Come to relax or to play while enjoying the spectacular sunsets and the blue waters of Key West! This ...
From $260 per night (USD)VRBO
From $322 per night (USD)HomeAway
~ POINCIANA PARADISE ~ Historic Home w/ Hot Tub & Parking for 2 Near Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: The Poinciana Paradise vacation rentals are located on a tiny lane in 'Old Town' Key West. This ...
From $322 per night (USD)HomeAway
From $150 per night (USD)VRBO
Key West Charming by AT HOME IN KEY WEST
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home ...
From $150 per night (USD)VRBO
From $450 per night (USD)HomeAway
Conch Republlic Cottage - Nightly Group Rental Unit - Sleeps up to 10 off Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This nightly group rental consists of 3 separate units, Porchside Paradise, Orange Blossom Suite and Deckside Suite. Co ...
From $450 per night (USD)HomeAway
From $180 per night (USD)VRBO
BRISA DEL MAR offers full Ocean view!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise, sunbathe, sunset, repeat! Enjoy spectacular ocean views from this lovely rental! This two bedroom, two bath co ...
From $180 per night (USD)VRBO
From $230 per night (USD)HomeAway
Pete's West Cottage steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $230 per night (USD)HomeAway
From $365 per night (USD)VRBO
Downtown Location in Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $365 per night (USD)VRBO
From $180 per night (USD)HomeAway
~ WISH UPON A STAR ~ Immaculate "Old Town" Home w/Pool & Parking,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: "Wish Upon a Star" is conveniently situated in the heart of "Old Town" Key West! Enjoy peace and q ...
From $180 per night (USD)HomeAway
From $179 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $179 per night (USD)VRBO
From $379 per night (USD)HomeAway
Renovated in Old Town, Private heated pool, 3 Block from Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated house with modern flare and Key West vibes and decor. This property is only available for rent on ...
From $379 per night (USD)HomeAway
From $180 per night (USD)VRBO
In the heart of Old Town - A Barefoot Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for the perfect home away from home? No need to look any further! No shoes needed at “A Barefoot Retreat” in t ...
From $180 per night (USD)VRBO
From $83 per night (USD)HomeAway
Kokomo by AT HOME IN KEY WEST
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Steps away from the large lagoon style pool surrounded w/lush tropical landscape. Everybody knows a little place like K ...
From $83 per night (USD)HomeAway
From $170 per night (USD)VRBO
~ SEA VISTA ~ Oceanfront Home, Pet Friendly, Fenced Yard, Pvt Pool & Parking
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 7
About THE PROPERTY: Just steps away from putting your toes in the ocean... Ever dream of waking up, walking out your ...
From $170 per night (USD)VRBO
From $279 per night (USD)HomeAway
Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Our luxurious condo is part of the brand new spectacular Beachside Resort & Conference Center. Beachside is Key West an ...
From $279 per night (USD)HomeAway
From $359 per night (USD)VRBO
Exclusive Key West Beach Front ~ Amazing View of the Ocean.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Rare, one-of-a kind designer luxury suite located in an exclusive gated beachfront property. Breath taking views overlo ...
From $359 per night (USD)VRBO
From $285 per night (USD)HomeAway
Artist Garden by AT HOME IN KEY WEST
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious home with a large outside deck is tucked away on a quiet lane of Truman Annex, yet only a short walk to al ...
From $285 per night (USD)HomeAway
From $240 per night (USD)VRBO
Duval Square Retreat: A beautiful condo steps from the action
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and quieter end of Duval ...
From $240 per night (USD)VRBO
From $350 per night (USD)HomeAway
Vintage Luxury Cottage ~ Hidden Duval Street Location - Private Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
"Vintage Luxury Cottage" - Just Off Upper Duval Street - Private Renovated Cottage with Private Pool Without a doubt, o ...
From $350 per night (USD)HomeAway
From $144 per night (USD)VRBO
~ INN COGNEATO COTTAGE ~ Gorgeous Home w/Pool in the <3 of Key West. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: Inn Cogneato is a newly renovated beautiful 2 bedroom 2 bath home located in one of the oldest par ...
From $144 per night (USD)VRBO
From $130 per night (USD)HomeAway
~ PETUNIA COTTAGE ~ Beautifully Renovated 'Old Town' Home w/ Outdoor Shower
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Just like its name, Petunia is a happy place. Open the picket gate, walk down the short, bricked w ...
From $130 per night (USD)HomeAway
From $100 per night (USD)VRBO
Sunset Suite - Gated Compound 1/2 Block Off Duval St. - Private spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunset Suite with daily housekeeping is a best kept secret! Overlooking the gardens, the entrance to this historic unit ...
From $100 per night (USD)VRBO
From $180 per night (USD)HomeAway
Bahamian Reed by AT HOME IN KEY WEST
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back ...
From $180 per night (USD)HomeAway
From $299 per night (USD)VRBO
Luxury Townhouse in the Gallery District of Old Town, Key West.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Luxury, 1,500 sq. ft. townhouse with 2 large bedrooms both with king beds, 3 full-size bathrooms plus covered parking fo ...
From $299 per night (USD)VRBO
From $190 per night (USD)HomeAway
~CASA KEY WEST~ Historical Home w/ Plunge Pool In PERFECT Location.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: As seen on HGTV's television series "ISLAND LIFE"! One of the Grand Dames of Key West, this two-s ...
From $190 per night (USD)HomeAway
From $200 per night (USD)VRBO
Water View property on Smathers Beach: 2 Bed / 2 Bath, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Peaceful views and tropical breezes of the natural salt ponds, acting as a bird sanctuary for native species, will help ...
From $200 per night (USD)VRBO
From $175 per night (USD)HomeAway
Large open air condo overlooking pool, fully appointed, 2 bikes provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Complex The Truman Annex is truly one of a kind in Key West. It is a gated community with impeccably kept grounds. ...
From $175 per night (USD)HomeAway
From $140 per night (USD)VRBO
Conch Adventure by AT HOME IN KEY WEST
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in a quiet corner of the Shipyard section in the desirable Truman Annex, this 2-bedroom 1 bath downstairs condo ...
From $140 per night (USD)VRBO
From $600 per night (USD)HomeAway
4 Bed/4 Bath Retreat at the End of the Road
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located at the end of the Florida Keys connected by road, Key West is both an oasis of calm and the launching pad for an ...
From $600 per night (USD)HomeAway
From $550 per night (USD)VRBO
Louisa House: A comfortable four bedroom vacation hideaway
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southe ...
From $550 per night (USD)VRBO
From $259 per night (USD)TripAdvisor
Best Location, 1/2 Block to Duval, Bimini Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The fa ...
From $259 per night (USD)TripAdvisor
From $159 per night (USD)PerfectPlaces
Newton's Nest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
NEWTON'S NEST (Monthly Rental) Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where y ...
From $159 per night (USD)PerfectPlaces