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From $4035 per night (USD)
VRBO
Multi-home tropical paradise with large, heated pool, & wraparound sundeck
Bedrooms:
6
Bathrooms:
6
Sleeps:
22
Papa's is close to everything, yet a genuinely secluded tropical paradise in Key West. Take the worry out of coordinatin ...
From $4035 per night (USD)
VRBO
From $650 per night (USD)
Expedia
Charming 2nd-story apartment with balcony & lighthouse view - walk everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Julia Whitehead Lighthouse Suites! Built in the 1890s on the site of what had been a small provisions and but ...
From $650 per night (USD)
Expedia
From $675 per night (USD)
VRBO
Tropical getaway with pool & sundeck - 1 block to Duval St, 2 blocks to beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This second-floor tropical studio has a private outdoor seating area and plenty of space for your vacation crew. Spend t ...
From $675 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Sunny condo with pool, lovely deck, central AC & washer/dryer - central location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great centra ...
From $530 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Pineapple Conch House
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to a vacationer’s contemporary conch house with 2-bedrooms, 2-baths, and a secluded pool and deck oasis. Room by ...
From $249 per night (USD)
VRBO
From $1200 per night (USD)
Expedia
**THE SOPHISTICATED SANDPIPER** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A lavish Key ...
From $1200 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Your Breezy Old Town Retreat Awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Breezy Key West First-Floor Condo w/ Pool Access Tucked into the heart of Old Town Key West, this first-floor condo is ...
From $296 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Pretty In Pink- Modern Comfort, Prime Location-2BD/2Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Tucked away in the exclusive Gardens of Key West community, this elegant single-family home offers the perfect blend of ...
From $259 per night (USD)
Expedia
From $849 per night (USD)
VRBO
**THE PLAYFUL PELICAN @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Thinking of f ...
From $849 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Poolside Paradise at Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Your Private Island Retreat Experience the ultimate Key West getaway in this luxury poolside townhome locate ...
From $204 per night (USD)
Expedia
From $334 per night (USD)
VRBO
Island Time on Washington : Stylish 4BR Key West Home, Heated Pool, Dogs OK, Parking & Near Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $334 per night (USD)
VRBO
From $1716 per night (USD)
Expedia
The Green Hour | 5BR Casa Marina Estate w/ Private Pool & Outdoor Kitchen
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
A Private Compound In Casa Marina formerly known as Plantation Tropicale Where The Day Naturally Shift ...
From $1716 per night (USD)
Expedia
From $28824 per night (USD)
VRBO
Steps to Duval St + Free Breakfast, Pool & Spa
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $28824 per night (USD)
VRBO
From $21317 per night (USD)
Expedia
Key West Beach Stay + Free Breakfast, Pool & Spa
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $21317 per night (USD)
Expedia
From $22666 per night (USD)
VRBO
Duval Street Stay + Free Breakfast, Beach & Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $22666 per night (USD)
VRBO
From $21317 per night (USD)
Expedia
Key West Beach Stay + Free Breakfast, Pool & Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $21317 per night (USD)
Expedia
From $22301 per night (USD)
VRBO
Duval Street Stay + Free Breakfast, Pool & Spa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $22301 per night (USD)
VRBO
From $22301 per night (USD)
Expedia
Duval Street Stay + Free Breakfast, Pool & Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $22301 per night (USD)
Expedia
From $22749 per night (USD)
VRBO
Beachfront Key West + Free Breakfast, Pool & Spa
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $22749 per night (USD)
VRBO
From $21670 per night (USD)
Expedia
Steps to Duval St + Free Breakfast, Pool & Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $21670 per night (USD)
Expedia
From $22666 per night (USD)
VRBO
Duval Street Stay + Free Breakfast. Private Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $22666 per night (USD)
VRBO
From $22749 per night (USD)
Expedia
Beachfront Key West + Free Breakfast, Bar & Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resor ...
From $22749 per night (USD)
Expedia
From $758 per night (USD)
VRBO
Mermaids Cove - Luxury Meets Location - 5BD/5.5Bath
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Welcome to Mermaid’s Cove, a stunning 5-bedroom, 5.5-bath luxury vacation home in the heart of Key West. Designed for co ...
From $758 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Hatteras Sleeps 8 & SelfDrive 20' Pontoon Fishing Lobstering Snorkeling Sandbar
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
The paired pontoon boat with this stay is a separete payment from your stay payment and is required within 7 days of the ...
From $257 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Seas the Breeze – Poolside Condo Near the Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
🌴 Seas the Breeze – Poolside Condo Near the Beach Relax in this poolside island retreat on the quiet side of Key Wes ...
From $395 per night (USD)
VRBO
From $397 per night (USD)
Expedia
A Cayo Hueso Retreat at the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A Cayo Hueso Retreat - This lovely, fully furnished, townhouse has 3 bedrooms and 2.5 baths . The master suite has a kin ...
From $397 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Walk to Southernmost Point! Conch Cottage w/ Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
2 Blocks to Hemingway Home | Designated Workspace | Laundry Machines Old Town Key West has a character all its own, and ...
From $412 per night (USD)
VRBO
From $122 per night (USD)
Expedia
Monthly 1-bedroom Apt B with kitchen, Old Town Key West.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This Key West apartment (B) boasts 1 inviting bedroom. Full kitchen, table and living room. Perfectly located in Old Tow ...
From $122 per night (USD)
Expedia
From $260 per night (USD)
VRBO
ZEN GARDEN RETREAT~NEW! Adult Only 3 BR with Treetop Suite/Writer Studio!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
**NEW LISTING** BRING YOUR SANDY FEET AND FLIP FLOPS ... Dive into ultimate island nirvana in this delightful cottage, ...
From $260 per night (USD)
VRBO
From $948 per night (USD)
Expedia
SANDY CHIC ~ NEW LISTING! Upscale 3 BR/3.5 Ba Home w/ Pool and Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
NEW LISTING! DREAMY OLD TOWN RETREAT… This Upper Duval classic abode exudes historic charm in quintessential Key West ...
From $948 per night (USD)
Expedia
From $672 per night (USD)
VRBO
**TASTE OF HAVANA @ DUVAL STREET** Home & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Experience th ...
From $672 per night (USD)
VRBO
From $529 per night (USD)
Expedia
**HAVANA ESPECIAL @ DUVAL** Cottage & Hot Tub + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! HAVANA ESPECI ...
From $529 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Key West Steps to Duval, Truman Waterfront Park and Beach. Walk everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Live like a local in the best Key West neighborhood situated just blocks from Duval Street and Ft. Zachary State Beach P ...
From $136 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Shared Pool + Backyard Lounge | Charming Cottage | Steps to Waterfront Dining
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Key West has a way of slowing everything down. The salt air, the swaying palms, the sense that your biggest decision of ...
From $186 per night (USD)
Expedia
From $478 per night (USD)
VRBO
Key West Paradise Found - Experience the Best Views at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Paradise Found – Oceanfront Luxury in Key West Welcome to Paradise Found, a beautifully renovated top-floor condo offer ...
From $478 per night (USD)
VRBO
From $404 per night (USD)
Expedia
Hyatt Beach House Key West - 2 bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Hyatt Beach House in beautiful Key West. Enjoy the lush tropical feel of this resort by kicking back and re ...
From $404 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Andros Suite | Perfect Location with Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Andros Suite Discover Andros Suite, a serene island hideaway just moments from the energy of Duval Street—where the cha ...
From $446 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Marvelous Newly Renovated 2-bedroom Dog Friendly home close to Duval & Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Sultan's Shanty! There’s no better way to spend a Key West vacation than in a freshly renovated home that ...
From $285 per night (USD)
Expedia
From $514 per night (USD)
VRBO
THE BLUE PINEAPPLE ~ Old Town 4 BR/4.4 Bath Home w/ Private Pool & Parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
A FUSION OF LUXURY AND HISTORY… This stunning Victorian estate has been meticulously renovated, offering the elegant all ...
From $514 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your Treetop Condo awaits. The welcoming garden atmosphere of this adorable tropical property is perfect for a tranquil ...
From $378 per night (USD)
Expedia
$\Porter Paradise at the Truman Annex in Key West\$
From $571 per night (USD)
VRBO
\"Porter Paradise at the Truman Annex in Key West\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming getaway in the prestigious Porter Court is located in the award winning Truman Annex in Old Town Key West. ...
From $571 per night (USD)
VRBO
From $548 per night (USD)
Expedia
POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
SPECTACULAR POOL HOME IN PEACEFUL SANCTUARY... Space, style and sunshine abound in this stunning 1926 single-story refug ...
From $548 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Blue Horizon Hideaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Waterfront 3BDR/2.5BA Key Cove Retreat, W/shared pool The Space: Welcome to Blue Horizon Hideaway, a spaci ...
From $292 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Quaint Key West Escape Old Town - Local Living
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Nestled in Key West, this adorable cottage features a cozy bedroom with a king bed, a well-equipped bathroom with a show ...
From $283 per night (USD)
Expedia
From $338 per night (USD)
VRBO
The Tipsy Mermaid at Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Tipsy Mermaid, your tropical retreat in the heart of the Key West Golf Club community. This stylish two-story ...
From $338 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Salt Ponds | Work & Relax in Key West | Poolside Condo • Balcony • Near Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your perfect Key West getaway! Located in the desirable Salt Ponds community, this beautifully maintained con ...
From $194 per night (USD)
Expedia
From $866 per night (USD)
VRBO
**VILLA PARADISO @ CASA EAST** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Welcome to VI ...
From $866 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Villa del Sol
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: Spacious Retreat with Pool & Guest Cottage The Space: Welcome to your tropical escape in one of Key West’s ...
From $429 per night (USD)
Expedia
From $689 per night (USD)
VRBO
Azure Vista Penthouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Ocean View Penthouse in Downtown Key West The Space: Oceanfront Penthouse at Historic Mills Place – Truman ...
From $689 per night (USD)
VRBO
From $518 per night (USD)
Expedia
Magical Ocean Penthouse – Top-Floor Ocean View Condo in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Magical Ocean Penthouse at 1800 Atlantic – Key West Experience the beauty of Key West from Magical Ocean Penthouse, a s ...
From $518 per night (USD)
Expedia
From $331 per night (USD)
VRBO
**DEEP BLUE DREAMS @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! As soon as yo ...
From $331 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Vitamin Sea at LaBrisa - Oceanfront View!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your Key West retreat. This well-appointed 2-bedroom, 2-bath residence offers a comfortable, elevated stay fo ...
From $254 per night (USD)
Expedia
From $1161 per night (USD)
VRBO
Slack Tide On Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Slack Tide: Location, location, location! Balcony overlooking Duval Street, just 2 blocks from the beach and Southernmos ...
From $1161 per night (USD)
VRBO
From $2713 per night (USD)
Expedia
Captain's Cove | Canalfront w/ Pool & Boat Lift
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Captain's Cove | Canalfront w/ Pool & Boat Lift Welcome to Captain's Cove, a stunning 4-bedroom, 4-bath waterfront retr ...
From $2713 per night (USD)
Expedia
From $767 per night (USD)
VRBO
Historic Cigar Barons Mansion
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Upscale historic cigar barons mansion in walking distance to everything you desire in Key West. 3 spacious 1Br’s with o ...
From $767 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Grinnell Old Town Hideaway Newly Renovated 1 Bed Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautifully renovated one bedroom apartment in the heart of Old Town Key West. No attention to detail has been spared wi ...
From $192 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Excitement on the Ocean Key West Oceanfront Condo Stunning Atlantic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Excitement on the Key West Ocean | Luxury Oceanfront Condo with Spectacular Atlantic Views Feel the excitement the mome ...
From $505 per night (USD)
VRBO
From $597 per night (USD)
Expedia
~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Flamingo Cottage is one of several cottages nestled down a gated walkway. Upon entering this two bedroom ...
From $597 per night (USD)
Expedia
From $595 per night (USD)
VRBO
~GARDENIA COTTAGE~18+ Adult Only cottage near Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
THE PROPERTY: Enjoy a soothing cup of coffee on the private patio or take an early morning walk on Mallory Square. This ...
From $595 per night (USD)
VRBO
From $645 per night (USD)
Expedia
POPEYE'S COTTAGE ~ NEW! Historic 3 BR/3Ba w/ Pool in Perfect Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
NEW LISTING! DISTINGUISHED LANDMARK GEM… Discover the irresistible appeal of Key West in this beautifully preserved Con ...
From $645 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Enjoy the best of Key West from this ideally located monthly rental just steps from the pool and close to Truman Waterfront, Fort Zachary Taylor State Park and Beach, Coffee Butler Amphitheater, and Duval Street. Private treetop deck.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cut and paste this video link https://www.youtube.com/watch?v=9mv1bfrtnjI Just steps to the pool and close ...
From $268 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Serendipity South: Premium Key West Pool Oasis Near The Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your tropical retreat! This stunning 3-bedroom, 2-bathroom home is perfect for the discerning traveler seekin ...
From $273 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Shipyard 297-Condo in Truman Annex-2 bedroom 2 bath, close to Duval w/ pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $257 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Ensuite Quad at The Hollinsed House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Hollinsed House's 2nd Floor "Victorian Delights" has a queen bed, large living room (with futon), dining area and r ...
From $404 per night (USD)
VRBO
From $366 per night (USD)
VRBO
King Ensuite at The Hollinsed House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The "Poolside Suite" on the 1st floor of the Carriage House building at the Hollinsed House is a large deluxe studio wit ...
From $366 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Queen Ensuite at The Hollinsed House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The "ShangriLa Suite" on the 1st floor of the Carriage House building at the Hollinsed House is a large deluxe studio wi ...
From $353 per night (USD)
VRBO
From $467 per night (USD)
VRBO
Apartment at The Hollinsed House
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
The "Caribbean Suite" on the 2nd floor of the Carriage House building at the Hollinsed House is a tropical 2BR/1BA with ...
From $467 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Monthly 1 bedroom apt-C with kitchen, Old Town Key West. Fantasy Fest 26 open
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This Key West apartment (C) boasts 1 inviting bedroom. Full kitchen, table and living room. Perfectly located in Old Tow ...
From $128 per night (USD)
Expedia
From $131 per night (USD)
VRBO
Old Town Studio Cottage with Full Kitchen, In-Unit Laundry & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming Studio Retreat with Pool Access in Old Town Key West. Escape to island living at this delightful studio located ...
From $131 per night (USD)
VRBO
From $430 per night (USD)
VRBO
Blue Flamingo Resort Key West | 2 Relaxing Ocean View Rooms for Your Stay
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located on North Roosevelt Boulevard, this resort offers convenient access to Key West’s vibrant downtown and popular at ...
From $430 per night (USD)
VRBO
From $236 per night (USD)
VRBO
Live the Island Life | Pool, Lawn Games, Cabanas & Karaoke Nights
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience luxury and space in this studio suite at Blue Flamingo Resort, offering uninterrupted ocean vistas. The suite ...
From $236 per night (USD)
VRBO
From $483 per night (USD)
Expedia
The Cayo Coco | Key West Condo with Pool, Hot Tub!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Cayo Coco | Key West Condo with Pool, Hot Tub & Balcony Views Welcome to The Cayo Coco, a beautifully updated 2-bed ...
From $483 per night (USD)
Expedia
From $495 per night (USD)
VRBO
The Grand Cayman | Beautifully Remodeled Key West!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Grand Cayman | Beautifully Remodeled Key West Condo! Escape to The Grand Cayman, a bright and beautifully appointed ...
From $495 per night (USD)
VRBO
From $497 per night (USD)
Expedia
The Saint Martin Suite | Delightfully Updated Beach Vibes!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Saint Martin Suite | Coastal-Chic Condo w/ Pool, Hot Tub & Balcony Views! Escape to The Saint Martin Suite, a brigh ...
From $497 per night (USD)
Expedia
From $499 per night (USD)
VRBO
The Saint Kitts Suite | Breathtaking View, Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Saint Kitts Suite | Dog-Friendly Key West Condo with Pool, Hot Tub & Balcony Views Escape to The Saint Kitts Suite, ...
From $499 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Ann Street Gardens
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $392 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Authors Retreat
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
This 2 bedroom, 1 ½ bath condo in the Campbell historic building offers a new translation for the word “vacation.” The v ...
From $187 per night (USD)
VRBO
From $879 per night (USD)
Expedia
-LUXURIOUS 4 Bd, 3.5 Bth off DUVAL-OLD TOWN-Modern, Pool/hot tub-Separate Studio
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Welcome to Pretty’s Place, A newly renovated home which blends modern luxury with timeless Key West character. Updated f ...
From $879 per night (USD)
Expedia
From $596 per night (USD)
VRBO
Two blocks from Southernmost Beach! Cozy One Bedroom Apartment.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Slack Tide Sunset : Location, location, location! Small Balcony looking towards the sunset, just 2 blocks from the beach ...
From $596 per night (USD)
VRBO
From $317 per night (USD)
Expedia
A Southard Pearl at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A "Southard Pearl" is a charming condo in the Shipyard in the Truman Annex and is outfitted with washer/dryer, pots/pans ...
From $317 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Jade Key walking distance to Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Jade Key a downtown Key West Home just Steps to Duval Street & Hemingway House! PROFESSIONAL Monthly rental ...
From $279 per night (USD)
VRBO
From $440 per night (USD)
Expedia
**WATERFRONT WHISPERS** Waterfront Home & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! WATERFRONT WH ...
From $440 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Blue Duval walking distance to Duval St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Blue Duval a downtown Key West Home just Steps to Duval Street & Hemingway House! PROFESSIONAL Monthly renta ...
From $299 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Road's End | Prime Old Town Location! Updated Home w/ Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Road's End Step into Road's End, your inviting retreat just steps from Duval Street, where the charm of Old Town Key We ...
From $446 per night (USD)
Expedia
From $635 per night (USD)
VRBO
WINDWARD SOUTH- Delightful 2-bedroom house with Pool in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to WINDWARD SOUTH — Your Peaceful Retreat in the Heart of Old Town Key West Discover the perfect blend of comfo ...
From $635 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Annie's Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The most important vacation element is location. This one-bedroom condo fits the bill precisely located in Truman Annex’ ...
From $171 per night (USD)
Expedia
From $197 per night (USD)
VRBO
Central Condo w/ Deck & Pool Access in Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gated Shipyard Condominiums Community | In-Unit Laundry Area Located in the Truman Annex and just a short walk away from ...
From $197 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Bikes Provided! Central Condo w/ Pool in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gated Community | In-Unit Laundry Area Located in the Truman Annex, less than a mile from vibrant Duval Street, museums ...
From $313 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Life Is A Breeze | Pool, Parking & Walk to Duval in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
***HOA regulations require a minimum stay of 6 nights and a maximum of 4 guests. No exceptions can be made. During peak ...
From $567 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Walkable Cottage w/ Pool Access in Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gated Community | Designated Workspace Centrally located in the Truman Annex near Bahama Village and Old Town, 'Sea Bre ...
From $278 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Bahama Village Sanctuary - Walkable & Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Bahama Village Sanctuary, a private Key West retreat in the heart of Old Town. This beautiful three-bedroom, ...
From $415 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Sunset Paradise at Sunset Marina-2 bed 2 bath oceanfront condo
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 $219 per night (USD)
Expedia
From $715 per night (USD)
VRBO
2 Bedroom Condo-Hyatt Beach House Key West-Ocean-Pool-Hot Tub-Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2-bedroom resort is perfect for your escape to Key West. Inside, guests find two king beds and a cozy living room w ...
From $715 per night (USD)
VRBO
From $886 per night (USD)
Expedia
Casa Riviera | Waterfront Hacienda w/ Pool & Boat Lift
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casa Riviera | Waterfront Hacienda w/ Pool & Boat Lift Escape to Casa Riviera, a private Key West waterfront retreat pe ...
From $886 per night (USD)
Expedia
From $179 per night (USD)
VRBO
TREEHOUSE ON MARGARET ~ NEW! Private 1 BR/2 Ba Single Family Home!
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
NEW LISTING! INTIMATE TROPICAL ESCAPE IN PRIVATE SINGLE FAMILY HOME… Don't let the 609 (1/2) fool you! This remodeled ...
From $179 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Lovely Day Chalet - Private Pool in Old Town
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Escape to The Lovely Day Chalet, a beautifully renovated 3-bedroom, 3.5-bath retreat nestled in the heart of Old Town Ke ...
From $406 per night (USD)
Expedia
From $1610 per night (USD)
VRBO
**THE DUKE & THE QUEEN** Compound w/ Pool + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
6
Sleeps:
18
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This compound ...
From $1610 per night (USD)
VRBO
From $1047 per night (USD)
Expedia
**DREAMSICLE by DUVAL @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Think back to ...
From $1047 per night (USD)
Expedia
From $2123 per night (USD)
VRBO
**THE EGRET & THE SANDPIPER** 2 Pool Compound + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2123 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to 921 Windsor Lane, a newly built coastal-modern retreat in the heart of Old Town Key West. Located just half a ...
From $700 per night (USD)
Expedia

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