Fleming Key Rentals
From $391 per night (USD)VRBO
Curry House | Heated Pool, King Bed, 1st Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $391 per night (USD)VRBO
From $835 per night (USD)Expedia
Private Parking, Heated Pool - Sweet Caroline
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $835 per night (USD)Expedia
From $546 per night (USD)VRBO
Private Parking , Heated Pool - Key Lime Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $546 per night (USD)VRBO
From $411 per night (USD)Expedia
Heated Pool, Epic Location - Sugar Pie Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $411 per night (USD)Expedia
From $376 per night (USD)VRBO
Heated Pool, Epic Location - Honeybun Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $376 per night (USD)VRBO
From $665 per night (USD)Expedia
Private Parking, Heated Pool - Banana Split
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $665 per night (USD)Expedia
From $445 per night (USD)VRBO
Heated Pool, Private Parking - Creme Brulee Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming historic conch home in the heart of Key West, just steps from the his ...
From $445 per night (USD)VRBO
From $1522 per night (USD)Expedia
3-Story spacious conch style home w/ private pool & dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1522 per night (USD)Expedia
From $517 per night (USD)VRBO
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $517 per night (USD)VRBO
From $473 per night (USD)Expedia
Carriage House at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $473 per night (USD)Expedia
From $324 per night (USD)VRBO
Bunk Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $324 per night (USD)VRBO
From $314 per night (USD)Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $314 per night (USD)Expedia
From $855 per night (USD)VRBO
Luxury Waterfront at Galion Resort in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $855 per night (USD)VRBO
From $507 per night (USD)Expedia
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You don’t oft ...
From $507 per night (USD)Expedia
From $534 per night (USD)VRBO
The Galleon Resort Best Resort Location in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $534 per night (USD)VRBO
From $246 per night (USD)Expedia
Anchors Away - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Away – Classic Conch Style Living in Old Town Key West Experience the charm of traditional Key West living at A ...
From $246 per night (USD)Expedia
From $533 per night (USD)VRBO
Red Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $533 per night (USD)VRBO
From $932 per night (USD)Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $932 per night (USD)Expedia
From $1589 per night (USD)VRBO
Oversized home for the whole family w/private pool & dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1589 per night (USD)VRBO
From $894 per night (USD)Expedia
Spacious home with pool & balcony - 1 block from Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Last Minute Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $894 per night (USD)Expedia
From $453 per night (USD)VRBO
Steps from Duval, Shared Pool – Sky Loft Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duv ...
From $453 per night (USD)VRBO
From $3802 per night (USD)Expedia
Takeover at the Grand Maloney
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick, ...
From $3802 per night (USD)Expedia
From $368 per night (USD)VRBO
NEW LISTING 2nd Fl Condo w/private outdoor deck overlooking historic Fleming St.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Airy sun-filled apartment above an art gallery in 100 year old Old Town Conch home. Private cozy quiet & romantic hideaw ...
From $368 per night (USD)VRBO
From $216 per night (USD)Expedia
Studio Apartment in the Casa Antigua, Hemingway's 1st Key West Hotel Residence
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful vacation home where you can relax and unwind with a friend and take you shoe off and enjoy nature. gorgeous s ...
From $216 per night (USD)Expedia
From $472 per night (USD)VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $472 per night (USD)VRBO
From $758 per night (USD)Expedia
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $758 per night (USD)Expedia
Click For PricingVRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For PricingVRBO
From $1814 per night (USD)Expedia
Features.Key West Suites Hotel has an outdoor pool and fitness center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $1814 per night (USD)Expedia
From $1107 per night (USD)VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $1107 per night (USD)VRBO
From $676 per night (USD)VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W/ 4+ Bedrooms/ 5.5 Baths
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $676 per night (USD)VRBO
From $767 per night (USD)VRBO
Two Bedroom Two Bath Balcony Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $767 per night (USD)VRBO
From $730 per night (USD)Expedia
Two Bedroom Two Bath Poolside Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $730 per night (USD)Expedia
From $371 per night (USD)VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
From $371 per night (USD)VRBO
From $1121 per night (USD)Expedia
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $1121 per night (USD)Expedia
From $859 per night (USD)VRBO
Casa Rosa: 4BR/4BA house, pool, near Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $859 per night (USD)VRBO
From $450 per night (USD)Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $450 per night (USD)Expedia
Click For PricingVRBO
Indoor / Outdoor Living in Old Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
Click For PricingVRBO
From $776 per night (USD)Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $776 per night (USD)Expedia
Click For PricingVRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For PricingVRBO
From $797 per night (USD)Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $797 per night (USD)Expedia
From $351 per night (USD)VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $351 per night (USD)VRBO
From $262 per night (USD)Expedia
Avail Oct 25 &26. fantasy fest parade Oct 25. grab it now before gone!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR STORM POLICIES ...
From $262 per night (USD)Expedia
From $948 per night (USD)VRBO
The Gideon Lowe House - Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance. Sophistication. Perfection. Welcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Ke ...
From $948 per night (USD)VRBO
From $1258 per night (USD)Expedia
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1258 per night (USD)Expedia
From $710 per night (USD)VRBO
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat ...
From $710 per night (USD)VRBO
From $791 per night (USD)Expedia
Downtown Key West 2BR/2BA•Pool, Dock, Pet \"Aruba\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room ...
From $791 per night (USD)Expedia
From $1744 per night (USD)VRBO
St. Johns Waterfront 4BR Penthouse•Pool•Dock•Park
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring the whole crew to this 2200 sqft waterfront penthouse—perfect for families & large groups! With 4 bedroom ...
From $1744 per night (USD)VRBO
From $702 per night (USD)Expedia
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $702 per night (USD)Expedia
From $1197 per night (USD)VRBO
Conch style home in Oldtown with private pool AND dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1197 per night (USD)VRBO
From $1335 per night (USD)Expedia
Luxury Waterfront Home with Private Pool and Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1335 per night (USD)Expedia
From $255 per night (USD)VRBO
Sept.mid wk.spec.117. lod +\n10 min walk beach, close to all +\nfull kitch& patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
SUMMER SPECIAL August and September Most dates @ 107. lodging plus extras per night. With 4 night stay 5th night FREE ...
From $255 per night (USD)VRBO
From $1131 per night (USD)Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $1131 per night (USD)Expedia
From $1066 per night (USD)VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $1066 per night (USD)VRBO
From $1074 per night (USD)Expedia
Washer & Dryer, Near Downtown - The Mesa House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $1074 per night (USD)Expedia
From $162 per night (USD)VRBO
Sunny Apartment with a Large Deck and Great View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming 1 bedroom second floor apartment with a large deck space for dining, sunbathing or watching sunsets. In residen ...
From $162 per night (USD)VRBO
From $402 per night (USD)Expedia
Our Piece of Paradise-
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $402 per night (USD)Expedia
From $631 per night (USD)VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $631 per night (USD)VRBO
From $248 per night (USD)Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $248 per night (USD)Expedia
From $1033 per night (USD)VRBO
Rooftop Penthouse, Walk to Duval - KAMP
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $1033 per night (USD)VRBO
From $471 per night (USD)Expedia
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the charm of historic Key West with a stay at The Elizabeth Suite, a recently renovated 1 bedroom, 1 bathroom ...
From $471 per night (USD)Expedia
From $402 per night (USD)VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The Fleming Suite, a 1 bedroom, 1 bathroom vacation rental located at The Bayview House in vibrant Key West. ...
From $402 per night (USD)VRBO
From $262 per night (USD)VRBO
Breezy Key West First-Floor Condo w/ Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $262 per night (USD)VRBO
From $312 per night (USD)VRBO
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $312 per night (USD)VRBO
From $480 per night (USD)VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $480 per night (USD)VRBO
From $446 per night (USD)VRBO
Quaint Bungalow w/ Private Outdoor Space Near Duval Street | Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $446 per night (USD)VRBO
From $528 per night (USD)VRBO
Celebrate History in Key West: Tropical Free Breakfast and Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $528 per night (USD)VRBO
From $433 per night (USD)VRBO
Serene Bungalow with Outdoor Pool Access | Free Breakfast Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $433 per night (USD)VRBO
From $483 per night (USD)VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $483 per night (USD)VRBO
From $461 per night (USD)VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool, Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $461 per night (USD)VRBO
From $482 per night (USD)VRBO
Serene Bungalow in Key West: Poolside Refreshers & Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $482 per night (USD)VRBO
From $465 per night (USD)VRBO
Tranquil Bungalow w/ an Artistic Vibe in Vibrant Key West | Breakfast Included
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)VRBO
From $439 per night (USD)VRBO
Stylish Room in the Heart of Old Town w/ Access to Outdoor Pool | Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $439 per night (USD)VRBO
From $519 per night (USD)VRBO
Historical Charm in a Room Surrounded by Key West's Best: Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $519 per night (USD)VRBO
From $393 per night (USD)VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $393 per night (USD)VRBO
From $2427 per night (USD)VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2427 per night (USD)VRBO
From $713 per night (USD)VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $713 per night (USD)VRBO
From $640 per night (USD)VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $640 per night (USD)VRBO
From $989 per night (USD)VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $989 per night (USD)VRBO
From $937 per night (USD)VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $937 per night (USD)VRBO
From $656 per night (USD)VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $656 per night (USD)VRBO
From $950 per night (USD)VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $950 per night (USD)VRBO
From $713 per night (USD)VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $713 per night (USD)VRBO
From $640 per night (USD)VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $640 per night (USD)VRBO
From $1801 per night (USD)VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1801 per night (USD)VRBO
From $2780 per night (USD)VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2780 per night (USD)VRBO
From $1230 per night (USD)VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1230 per night (USD)VRBO
From $939 per night (USD)VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $939 per night (USD)VRBO
From $1907 per night (USD)VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1907 per night (USD)VRBO
From $683 per night (USD)VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation Fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $683 per night (USD)VRBO
From $1230 per night (USD)VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1230 per night (USD)VRBO
From $1907 per night (USD)VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1907 per night (USD)VRBO
From $656 per night (USD)VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $656 per night (USD)VRBO
From $678 per night (USD)VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $678 per night (USD)VRBO
From $606 per night (USD)VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $606 per night (USD)VRBO
From $939 per night (USD)VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $939 per night (USD)VRBO
From $1051 per night (USD)VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1051 per night (USD)VRBO
From $933 per night (USD)VRBO
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $933 per night (USD)VRBO
From $2427 per night (USD)VRBO
4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2427 per night (USD)VRBO
From $2775 per night (USD)VRBO
3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2775 per night (USD)VRBO
From $1132 per night (USD)VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1132 per night (USD)VRBO