Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $285 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 6
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Curry House offers three stories of historic Conch house charm, perfect for your getaway. This guesthouse featu ...
From $285 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Balcony, Pool, Near Duval - Curry House Room 3 + 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Curry House offers three stories of historic charm, transporting you back in time. The guesthouse features priv ...
From $389 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $285 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 8
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 $280 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 7
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 $280 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Balcony, Pool, & Near Duval - Curry House Room 2
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 $290 per night (USD)
Expedia
From $284 per night (USD)
VRBO
Balcony, Pool, & Near Duval - Curry House Room 9
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 $284 per night (USD)
VRBO
From $285 per night (USD)
Expedia
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 $285 per night (USD)
Expedia
From $632 per night (USD)
VRBO
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 $632 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $349 per night (USD)
VRBO
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 $349 per night (USD)
VRBO
From $349 per night (USD)
Expedia
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 $349 per night (USD)
Expedia
From $395 per night (USD)
VRBO
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 $395 per night (USD)
VRBO
From $354 per night (USD)
Expedia
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 $354 per night (USD)
Expedia
From $669 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 $669 per night (USD)
VRBO
From $334 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 $334 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 $304 per night (USD)
Expedia
Anchors Away - Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $304 per night (USD)
Expedia
From $336 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 $336 per night (USD)
VRBO
From $1299 per night (USD)
Expedia
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 $1299 per night (USD)
Expedia
From $821 per night (USD)
VRBO
**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 $821 per night (USD)
VRBO
From $1082 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 $1082 per night (USD)
Expedia
From $468 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 $468 per night (USD)
VRBO
From $3155 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 $3155 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 $1996 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 $1996 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $448 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 $448 per night (USD)
VRBO
From $636 per night (USD)
VRBO
~ 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 $636 per night (USD)
VRBO
From $1051 per night (USD)
Expedia
**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 $1051 per night (USD)
Expedia
From $753 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 $753 per night (USD)
VRBO
From $506 per night (USD)
Expedia
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 $506 per night (USD)
Expedia
From $506 per night (USD)
VRBO
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 $506 per night (USD)
VRBO
From $371 per night (USD)
Expedia
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)
Expedia
From $915 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 $915 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 Pricing
VRBO
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 Pricing
VRBO
From $759 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 $759 per night (USD)
Expedia
From $341 per night (USD)
VRBO
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 $341 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $1152 per night (USD)
VRBO
**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 $1152 per night (USD)
VRBO
From $243 per night (USD)
Expedia
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 $243 per night (USD)
Expedia
From $404 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 $404 per night (USD)
VRBO
$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $400 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 $400 per night (USD)
Expedia
From $1718 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 $1718 per night (USD)
VRBO
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $400 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 $400 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Key West Hideaway, ½ Mile to Beach,Walkable, Peaceful, Well-Equipped!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR STORM POLICIES ...
From $234 per night (USD)
VRBO
From $881 per night (USD)
Expedia
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $881 per night (USD)
Expedia
From $844 per night (USD)
VRBO
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 $844 per night (USD)
VRBO
From $1042 per night (USD)
Expedia
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 $1042 per night (USD)
Expedia
From $1078 per night (USD)
VRBO
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 $1078 per night (USD)
VRBO
$Spec @107.lodg+ Aug & sept. \n10 min walk beach, close to all +\nfull kitch& patio$
From $196 per night (USD)
Expedia
Spec @107.lodg+ Aug & sept. \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 $196 per night (USD)
Expedia
From $618 per night (USD)
VRBO
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 $618 per night (USD)
VRBO
From $668 per night (USD)
Expedia
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 $668 per night (USD)
Expedia
From $909 per night (USD)
VRBO
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 $909 per night (USD)
VRBO
From $500 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 $500 per night (USD)
Expedia
From $408 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 $408 per night (USD)
VRBO
From $212 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 $212 per night (USD)
Expedia
From $746 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 $746 per night (USD)
VRBO
From $308 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 $308 per night (USD)
Expedia
From $497 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool, monthly rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Fleming Suite, a beautifully refreshed 1 bedroom, 1 bathroom vacation rental located at The Bayview House ...
From $497 per night (USD)
VRBO
From $284 per night (USD)
Expedia
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 $284 per night (USD)
Expedia
From $2097 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 $2097 per night (USD)
VRBO
From $731 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 $731 per night (USD)
VRBO
From $543 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 $543 per night (USD)
VRBO
From $1059 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 $1059 per night (USD)
VRBO
From $919 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 $919 per night (USD)
VRBO
From $557 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 $557 per night (USD)
VRBO
From $796 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 $796 per night (USD)
VRBO
From $731 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 $731 per night (USD)
VRBO
From $543 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 $543 per night (USD)
VRBO
From $1514 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 $1514 per night (USD)
VRBO
From $3076 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 $3076 per night (USD)
VRBO
From $1009 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 $1009 per night (USD)
VRBO
From $916 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 $916 per night (USD)
VRBO
From $1930 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 $1930 per night (USD)
VRBO
From $534 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 $534 per night (USD)
VRBO
From $1009 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 $1009 per night (USD)
VRBO
From $1930 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 $1930 per night (USD)
VRBO
From $556 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 $556 per night (USD)
VRBO
From $534 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 $534 per night (USD)
VRBO
From $483 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 $483 per night (USD)
VRBO
From $916 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 $916 per night (USD)
VRBO
From $1059 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 $1059 per night (USD)
VRBO
From $919 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 $919 per night (USD)
VRBO
From $2097 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 $2097 per night (USD)
VRBO
From $3076 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 $3076 per night (USD)
VRBO
From $796 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 $796 per night (USD)
VRBO
From $1514 per night (USD)
VRBO
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
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 $1514 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Southard Retreat- 2 bed 2 bath townhome downtown w/ pool, parking
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 $191 per night (USD)
Expedia
From $462 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 $462 per night (USD)
VRBO
From $589 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 $589 per night (USD)
VRBO
From $432 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 $432 per night (USD)
VRBO
From $602 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 $602 per night (USD)
VRBO
From $449 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 $449 per night (USD)
VRBO
From $465 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 $465 per night (USD)
VRBO
From $922 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 $922 per night (USD)
VRBO
From $428 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 $428 per night (USD)
VRBO
From $836 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 $836 per night (USD)
VRBO
From $436 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 $436 per night (USD)
VRBO

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