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Listings in "Key West"

Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!
$ 205 /night
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ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
$ 183 /night
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Serene dog-friendly haven with pool access, central AC, & walkable locale
$ 239 /night
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Secret Casita: Relaxing 2BD/2BA escape RealKeyWest
$ 125 /night
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Downtown Waterfront Penthouse Pool, Dock, Parking
$ 945 /night
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Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
$ 762 /night
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Downtown Waterfront Penthouse Pool, Parking, Dock
$ 972 /night
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Pelican Landing Falmingo-2bedroom waterfront condo w/boat slip, parking
$ 337 /night
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Waterfront Penthouse sleeps 16 w/Pool & Boat Dock
$ 978 /night
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Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
$ 1,014 /night
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Seafarer’s Refuge: 3 Story spacious conch style home w/ private pool & dock!
$ 1,010 /night
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Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
$ 632 /night
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Pelican Landing Dominica-2bedroom waterfront condo w/boat slip, parking
$ 312 /night
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Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
$ 581 /night
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Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
$ 627 /night
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Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
$ 833 /night
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Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
$ 588 /night
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Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
$ 4,274 /night
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Downtown 4/4 Waterfront Penthouse Pool, Dock, Pet
$ 978 /night
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Pelican Landing Bermuda-2bedroom waterfront condo w/boat slip, parking
$ 280 /night
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Large 2/2 Waterfront Condo Great View Pool & Dock
$ 399 /night
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Captain’s Daughter: Oversized home for the whole family w/private pool & dock
$ 1,236 /night
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Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
$ 984 /night
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Downtown Waterfront 2/2 Dock & Pool Pet-Friendly
$ 390 /night
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Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
$ 754 /night
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Spacious 2/2 Waterfront Condo w/Pool&Dock
$ 401 /night
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Large waterfront 2/2 end unit with boat slip
$ 385 /night
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Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
$ 896 /night
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Bayview Manor at Paradise Harbor with Private Pool and Dock!
$ 1,068 /night
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Shipyard 276-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
$ 237 /night
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Always Your Paradise by AvantStay | Shared Pool | Near Zachary Beach!
$ 183 /night
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Best location in town. Walk or ride and cover the whole island.
$ 291 /night
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Gulf Getaway by Brightwild | Condo w/Pool!
$ 156 /night
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SOUTHARD COMFORT at The Truman Annex in Key West
$ 287 /night
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Cozy Piece of Key West History
$ 237 /night
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Eleanor’s Place in Key West Old Town – Dogs Ok with Parking.
$ 315 /night
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La Paloma- Updated Old Town 2 bedroom 1 bath home w/ jacuzzi backyard oasis
$ 188 /night
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**BAHAMIAN BLUES @ BAHAMA VILLAGE** Impeccable Home & Pool + LAST KEY SERVICES…
$ 814 /night
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@ KEY WEST DOWNTOWN STUDIO APT AMAZING PRICES SUMMER 2023 & Winter 2023/2024
$ 79 /night
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Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg/bikes
$ 177 /night
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Sunny Side Up- 3 BDR/2BA | 4 Bed, 3 Bath
$ 270 /night
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SWEET DREAMS ARE MADE OF ‘THE KEYS’ ~ Bahama Village 2 BR/2 Ba Home w/ Pool!
$ 435 /night
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~ INN COGNEATO ~Experience island life in a private oasis with heated pool.
$ 219 /night
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Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
$ 197 /night
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MONTHLY RENTAL, block to Duval, POOL, your own personal resort, 3 BR/ 3 BA
$ 158 /night
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SPARKLING Old Town KW PRIVATE 3BR Home Lagoon Pool FREE Bikes Steps to Duval
$ 138 /night
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Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
$ 99 /night
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Historic house near Duval Street
$ 278 /night
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Conch Haven luxury 1 Bedroom Old Town MONTHLY
$ 163 /night
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King Bed Room in the Heart of Key West! Perfect for Friends & Couples Vacation
$ 245 /night
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Amelia by the Sea in Key West
$ 254 /night
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Amelia Street Retreat: Updated 3BR Key West Home, 2 Blocks to Duval St, Relaxing Patio & Parking!
$ 208 /night
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Southern Skies, Stylish Home in Old Town Key West
$ 279 /night
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Updated Old Town condo with pool & parking 5 min walk to Duval and Truman Park
$ 347 /night
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Charming, newly renovated Key West home2 bed, 1 bath with bonus loft bedroom
$ 165 /night
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Beautiful, private, bright one bedroom cottage walk to Duval, Truman Waterfront, Santiago’s Bodega
$ 103 /night
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Mirabella- updated Old Town home w/ private pool oasis, parking, 2 bed 2 bath
$ 147 /night
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Serenity by AvantStay | Guest House in Old Town w/ Shared Pool
$ 121 /night
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~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.
$ 142 /night
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Peachy Keen: Parking, Private Pool, Dogs Ok near Truman Annex
$ 254 /night
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~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.
$ 132 /night
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La Casita by AvantStay | Steps to Duval Street | Month Long Stays Only
$ 103 /night
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Key West – Historic & Charming – Main House
$ 1,230 /night
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Queen’s Lair Rockhouse
$ 187 /night
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PARADISE ON PORTER in the Truman Annex
$ 324 /night
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ANGEL FISH at The Truman Annex in Key West
$ 299 /night
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Truman Annex Townhome w/pool Key west
$ 315 /night
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Stylish Condo with Swimming Pool – Minutes from Popular Attractions
$ 390 /night
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Old Town Key West Historic Cigarmaker’s Cottage – Sleeps 5
$ 533 /night
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Old Town Cottage House in Old Town Key West!
$ 100 /night
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Old Town Key West – Historic & Charming – 2 Blks From Duval
$ 630 /night
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Key West Old Town Rental Compound – Private, Sleeps 20
$ 3,031 /night
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**THE PIRATE’S PENTHOUSE @ BAHAMA VILLAGE** Centrally Located Condo + LAST KEY S
$ 340 /night
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CHANGES IN LATITUDES ~ Renovated 3 BR/2.5 Ba Home w/ Pool!
$ 197 /night
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BEACHY KEEN ~ Charming 1 BR, 1 Ba Home w/ Loft in Great Location!
$ 91 /night
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Bahama Village studio @ the Galleria!
$ 160 /night
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Bayfront bungalow with private dock, kayaks, SUPs, tiki hut & pool access
$ 203 /night
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Castaway Cove: 2/2 Condo near the beach with shared pool and hot tub
$ 233 /night
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Truman Annex, two blocks from Duval
$ 248 /night
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SALTWATER ANGLER at The Truman Annex in Key West
$ 479 /night
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Sunset Harbor – Old Town Key West Location – Beautiful Property
$ 593 /night
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CATCH OF THE DAY at The Truman Annex in Key West
$ 647 /night
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Sea-Shells Harbour Place at Truman Annex in Key West
$ 712 /night
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Peaceful 2 BR Condo with All Amenities
$ 180 /night
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Upscale dog-friendly home on golf course with lush back yard & pool
$ 180 /night
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Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking – Dog OK
$ 266 /night
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NEW! Atlantic Escape by Brightwild – Beach & Pool
$ 132 /night
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Wonderful Condo in Key West w/Free WiFi, Lanai, A/C, Shared Hot Tub & Pool
$ 173 /night
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BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE
$ 144 /night
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Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
$ 333 /night
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A HARBOUR ROOST at The Truman Annex in Key West
$ 470 /night
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OCEAN BREEZE at The Truman Annex in Key West
$ 470 /night
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Sunset Harbor – Old Town Key West Location – Beautiful Property
$ 426 /night
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Banana Key in Key West
$ 274 /night
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Shipyard Truman Annex 1st Floor End Unit
$ 132 /night
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“Paradise Found” in Historic Key West
$ 245 /night
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SWEET LIKE SUMMERTIME ~ 3 BR/2Ba Home w/ Pool and Yard!
$ 173 /night
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Sweet Caroline Historic Seaport Key West Home Rental Floor 2
$ 236 /night
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Southard Love – 2.5 Blocks to Downtown, Walk to Beach. 4 Bedrooms, 3 Baths
$ 402 /night
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LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!
$ 218 /night
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