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From $787 per night (USD)
VRBO
Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $787 per night (USD)
VRBO
From $1455 per night (USD)
Expedia
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Resembling a ...
From $1455 per night (USD)
Expedia
From $715 per night (USD)
VRBO
Bermuda Retreat-waterfront 2BR 2BA condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $715 per night (USD)
VRBO
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Expedia
Dog-friendly home w/ large private pool only a short walk to Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
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Expedia
From $260 per night (USD)
VRBO
Boater's Dream 2Bed 2Bath Condo, 30 night stay w/ water views, balcony, pool
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 $260 per night (USD)
VRBO
From $882 per night (USD)
VRBO
ARTIST'S CONDO @ Duval Square by Rent Key West Vacations - Located on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Duval Square is a charming community with shops and restaurants downstairs and secure, quiet, private residences, pool a ...
From $882 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Flamingo Retreat-waterfront 2BR 2BA condo w/ pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $693 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w/ pool
Bedrooms:
1
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 $404 per night (USD)
VRBO
From $322 per night (USD)
VRBO
The Palms -3 bedroom 2 bath home in The Meadows w/ pool oasis & guest cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $322 per night (USD)
VRBO
From $707 per night (USD)
VRBO
Duval Square Retreat: A beautiful condo steps from the action
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Duval Square Retreat is In the heart of Old Town. Duval Square is located at the "artistic" and quieter end of Duval St ...
From $707 per night (USD)
VRBO
From $554 per night (USD)
VRBO
Little Paradise, Historic Harbor Old Town Key West 2/1.5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $554 per night (USD)
VRBO
From $594 per night (USD)
VRBO
Truman Annex unit 254
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $594 per night (USD)
VRBO
From $952 per night (USD)
VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $952 per night (USD)
VRBO
From $1000 per night (USD)
VRBO
Hyatt Sunset Harbor Resort for ONLY Sunday to Sunday Week's stay.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is for A WEEK'S Stay Only in a 2 Bedroom 2 Bathroom Villa for 6 People. Discover this relaxing oasis in the heart ...
From $1000 per night (USD)
VRBO
From $481 per night (USD)
VRBO
Key West GULF FRONT Home with Private Dock and Heated Pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own priva ...
From $481 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Oasis in Old Town - our special home
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Our sweet ‘conch’ cottage in old town Key West has been completely redesigned and custom crafted by 2 architects as our ...
From $267 per night (USD)
VRBO
Click For Pricing
VRBO
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For Pricing
VRBO
From $416 per night (USD)
Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $416 per night (USD)
Expedia
From $463 per night (USD)
VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $463 per night (USD)
VRBO
From $414 per night (USD)
Expedia
Great Family Vacation Rental.
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $414 per night (USD)
Expedia
From $791 per night (USD)
VRBO
Classic Key West cottage with pool & courtyard - walk to beach & Duval St dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Papa's Hideaway - Garden of Eden Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $791 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $568 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Barts Suite 303 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $577 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $257 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Queen’s Lair Rockhouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $306 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Sunny Tropical Condo with WiFi & Pool - Close to Beachside Action
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Seashore at the Shipyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $314 per night (USD)
Expedia
From $3794 per night (USD)
VRBO
Multi-home tropical paradise with large, heated pool, & wraparound sundeck
Bedrooms:
6
Bathrooms:
6
Sleeps:
22
Papa's Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $3794 per night (USD)
VRBO
From $579 per night (USD)
Expedia
Comfortable Condo with Pool, Private Balcony, & Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $579 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $499 per night (USD)
VRBO
From $972 per night (USD)
Expedia
Charming dog-friendly home with guest cottage & private pool - great location
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $972 per night (USD)
Expedia
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VRBO
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For Pricing
VRBO
From $870 per night (USD)
Expedia
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Amelia House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $870 per night (USD)
Expedia
From $537 per night (USD)
VRBO
**CONCH GET ENOUGH at The Truman Annex in Key West**
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $537 per night (USD)
VRBO
From $4164 per night (USD)
Expedia
Key West Oasis - Truman Annex Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Welcome to Key West Oasis Luxury | Privacy | Iconic Location in Truman Annex Tucked away on one of the most exclusive ...
From $4164 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Modern 2BR Condo Old Town/Balcony & Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $217 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Green Goddess - 4 BD/3 BA Amazing 360 Degrees Rooftop Views! RealKeyWest
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $501 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Heart of Downtown Key West Cottage With Off-Street Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minut ...
From $486 per night (USD)
VRBO
From $802 per night (USD)
Expedia
Balcony & Near Downtown - Sky Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $802 per night (USD)
Expedia
From $1395 per night (USD)
VRBO
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! All year long ...
From $1395 per night (USD)
VRBO
From $881 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $881 per night (USD)
Expedia
From $828 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $828 per night (USD)
VRBO
From $879 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $879 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Ocean-breeze Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This property recently fully renovated. Original house was built in 1892. 1 bedroom 1 bathroom apartment with hardwood f ...
From $160 per night (USD)
VRBO
From $916 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $916 per night (USD)
Expedia
From $816 per night (USD)
VRBO
Southard Love: 2.5 Blocks to Duval, beach & historic seaport. 4 Beds, 3 Baths
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
'SOUTHARD LOVE' is located on Southard Street on the corner of LOVE Lane This home is a perfect example of WHY people c ...
From $816 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Beautiful Upper Duval - Uptown - 2 bedroom Condo
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Location, Location!!Welcome to our Key West Condo! This beautiful Upper Duvalcondo is walkable to everything in Key West ...
From $261 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Fairway Villa w/ Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Fairway Villa — a stunning, spacious 3-bedroom, 3-bathroom townhouse nestled on the beautiful Key West Golf C ...
From $247 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Book it before it's gone - 7 day rental - available from Saturday 11/14/26 to Saturday 11/21/26 only. Cozy and comforta ...
From $225 per night (USD)
Expedia
From $325 per night (USD)
VRBO
ShangriLa Suite / Queen Studio / Sleeps 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $325 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Tropical Paradise In Key West-Coconut Beach Resort - Avail 4/25/25 to 5/2/26
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Book it before it's gone! 7 Day rental - available from Saturday 4/25/26 to Saturday 5/2/26 only. Cozy and comfortable ...
From $326 per night (USD)
VRBO
From $338 per night (USD)
VRBO
LA PUERTA ROSA~Charming 3 bed/2 bath Conch Home in Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $338 per night (USD)
VRBO
From $220 per night (USD)
VRBO
Single Family Home, 3 Bedroom, 2 Baths, Pool. Great Value!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private b ...
From $220 per night (USD)
VRBO
From $524 per night (USD)
VRBO
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $524 per night (USD)
VRBO
From $175 per night (USD)
VRBO
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $175 per night (USD)
VRBO
From $3628 per night (USD)
VRBO
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
Bedrooms:
14
Bathrooms:
13
Sleeps:
32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $3628 per night (USD)
VRBO
From $675 per night (USD)
VRBO
Key West On THE BEACH New Years! Dec 27th - Jan 3rd 2026
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER This rental is for a 7 NIGHT HOLIDAY 1 week RENTAL ONLY! This is for 7 n ...
From $675 per night (USD)
VRBO
From $1929 per night (USD)
VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1929 per night (USD)
VRBO
From $755 per night (USD)
VRBO
2-Bedroom Villa at Hyatt Beach House! Quiet Beachfront Location! Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $755 per night (USD)
VRBO
From $2485 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
4
Sleeps:
16
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $2485 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $301 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Relaxing island home/Great location/Stylish
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $253 per night (USD)
VRBO
From $731 per night (USD)
Expedia
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
Bedrooms:
0
Bathrooms:
4
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $731 per night (USD)
Expedia
From $919 per night (USD)
VRBO
Luxury Private Home w/ Heated Pool in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
28 DAY MINIMUM. This gated property includes a 3 bedroom 2 bathroom main house (main level) PLUS a 1 bedroom 1 bathroom ...
From $919 per night (USD)
VRBO
From $341 per night (USD)
Expedia
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $341 per night (USD)
Expedia
From $336 per night (USD)
VRBO
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $336 per night (USD)
VRBO
From $330 per night (USD)
Expedia
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $330 per night (USD)
Expedia
From $580 per night (USD)
VRBO
ISLAND OASIS in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $580 per night (USD)
VRBO
Click For Pricing
Expedia
Pet friendly Monthly Rental with Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lush tropical grounds greet you upon entrance of this enhanced 3/2 monthly rental home. This adorable retreat is located ...
Click For Pricing
Expedia
From $419 per night (USD)
VRBO
SOUTHERN CROSS ~ Conveniently Located 3 Bedroom, 2.5 Bathroom Gem w/ Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
SOUTHERN HOSPITALITY... Find your luxurious, island retreat nestled in the heart of Old Town, just blocks from the beaut ...
From $419 per night (USD)
VRBO
From $190 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town Duplex, private backyard, pets welcome, 2BR/2BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $190 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w/ balcony at Mile Marker 0!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 full bath {queen ...
From $472 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $692 per night (USD)
Expedia
From $885 per night (USD)
VRBO
Duval Street, Condo, Luxury,
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
We know that you will enjoy staying in this oasis of comfort in the paradise of Key West. Our Cuban Club Condo is a 1500 ...
From $885 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Yellow 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 $504 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Blue 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 $540 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Green 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 $504 per night (USD)
Expedia
From $271 per night (USD)
VRBO
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $271 per night (USD)
VRBO
From $224 per night (USD)
Expedia
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $224 per night (USD)
Expedia
From $370 per night (USD)
VRBO
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $370 per night (USD)
VRBO
From $451 per night (USD)
Expedia
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w/ Parking in Perfect Location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $451 per night (USD)
Expedia
From $233 per night (USD)
VRBO
Duval Street Suites on Duval Free Parking and heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $233 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Duval Street Suites full kitchen, free parking, & heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $255 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Duval Street Suites full kitchen, free parking, heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Old ...
From $252 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Duval Street Suites full kitchen and heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking ...
From $243 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Duval Street Suites with full kitchen heated pool, free parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (king) and kitchen. Overlooking Duva ...
From $234 per night (USD)
VRBO
From $2736 per night (USD)
Expedia
6 BR 6 BA Guesthouse Suites on Duval free parking, private pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with 6 individual suites each eq ...
From $2736 per night (USD)
Expedia
From $448 per night (USD)
VRBO
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $448 per night (USD)
VRBO
From $180 per night (USD)
Expedia
MONTHLY RENTAL, Old Town Duplex, private backyard, 2 BR/2 BA, pets ok
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $180 per night (USD)
Expedia
From $731 per night (USD)
VRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
From $731 per night (USD)
VRBO
From $580 per night (USD)
Expedia
Parking, Pool, Near Duval St - Poolside Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $580 per night (USD)
Expedia
From $433 per night (USD)
VRBO
AWAY FROM IT ALL @ The Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $433 per night (USD)
VRBO
From $619 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $619 per night (USD)
Expedia
From $2070 per night (USD)
VRBO
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $2070 per night (USD)
VRBO
From $411 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $411 per night (USD)
Expedia
From $833 per night (USD)
VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $833 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Pet Friendly, Pool, Free Parking - The Grand Turk
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $515 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Duval Street Suites full kitchen Old Town with heated pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $561 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Ocean views and beach breezes at La Brisa's #303 West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
28 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your balcony overlooking the salt ponds, a ...
From $428 per night (USD)
VRBO
From $666 per night (USD)
VRBO
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $666 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $483 per night (USD)
Expedia

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