Key West Rentals
- From $363 per night (USD)
VRBO
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUZY'S PARROT ...
From $363 per night (USD)VRBO
- From $721 per night (USD)
Expedia
Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breeze ...
From $721 per night (USD)Expedia
- From $309 per night (USD)
VRBO
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES.
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is t ...
From $309 per night (USD)VRBO
- From $1441 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 $1441 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Dog-friendly home w\/ large private pool only a short walk to Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $256 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $206 per night (USD)
VRBO
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 $206 per night (USD)VRBO
- From $424 per night (USD)
Expedia
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 $424 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Great Family Vacation Rental.
- Bedrooms:
- 3
- 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 $275 per night (USD)VRBO
- From $124 per night (USD)
Expedia
Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $124 per night (USD)Expedia
- From $149 per night (USD)
VRBO
Stylish Dog-Friendly Condo with Balcony - In Heart of the Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kingfish Keep On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $149 per night (USD)VRBO
- From $193 per night (USD)
Expedia
Condo on Duval with WiFi, Hot Tub, & Private Parking - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Duval Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $193 per night (USD)Expedia
- From $108 per night (USD)
VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $108 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Village - Tropical Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $324 per night (USD)Expedia
- From $139 per night (USD)
VRBO
Contemporary Seaside Cottage with a Private Hot Tub & Shared, Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Heron Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $139 per night (USD)VRBO
- From $385 per night (USD)
Expedia
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 $385 per night (USD)Expedia
- From $281 per night (USD)
VRBO
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 $281 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Queen’s Lair Rockhouse
- Bedrooms:
- 3
- 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 $225 per night (USD)Expedia
- From $237 per night (USD)
VRBO
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $237 per night (USD)VRBO
- Click For Pricing
Expedia
Fresh Getaway w\/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Hueso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For PricingExpedia
- From $198 per night (USD)
VRBO
Condo on Duval Street - Walk to Beach & Southernmost Point, Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Yellowfin Ledge On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $198 per night (USD)VRBO
- From $486 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 $486 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Amazing condo with pool & hot tub - ideal for exploring Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrise Suites - Cat Island Suite 205 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $385 per night (USD)VRBO
- From $158 per night (USD)
Expedia
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $158 per night (USD)Expedia
- From $324 per night (USD)
VRBO
Dog-Friendly Retreat in Casa Marina with Shared Pool, WiFi, and Walkable Locale
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Tropical Village - Toon Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $324 per night (USD)VRBO
- From $2512 per night (USD)
Expedia
Spacious dog-friendly retreat with 3 hot tubs - near Duval Street & the beach
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Southernmost Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $2512 per night (USD)Expedia
- From $239 per night (USD)
VRBO
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Bonaire Suite 210 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $239 per night (USD)VRBO
- From $183 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 $183 per night (USD)Expedia
- From $285 per night (USD)
VRBO
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $285 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $180 per night (USD)Expedia
- From $213 per night (USD)
VRBO
Dog-friendly resort condo with pool & hot tub, private parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Saint Croix Suite 212 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $213 per night (USD)VRBO
- From $192 per night (USD)
Expedia
Dog-friendly condo in prime location - walk to dining & sights, near the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $192 per night (USD)Expedia
- From $772 per night (USD)
VRBO
Southernmost View by Brightwild | Pool & H20 Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fro ...
From $772 per night (USD)VRBO
- From $764 per night (USD)
Expedia
Lovely 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 $764 per night (USD)Expedia
- From $316 per night (USD)
VRBO
Serene dog-friendly haven with pool access, central AC, & walkable locale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tropical Village - Southern Cross Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $316 per night (USD)VRBO
- From $386 per night (USD)
Expedia
Little Paradise, Historic Harbor Old Town Key West 2\/2
- Bedrooms:
- 2
- 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 $386 per night (USD)Expedia
- Click For Pricing
VRBO
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
- Bedrooms:
- 2
- 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 PricingVRBO
- From $187 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 $187 per night (USD)Expedia
- From $227 per night (USD)
VRBO
Peaceful condo in Duval Square\/Old Town with lush gardens, pool, & chic decor
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Bonita at Duval Square R1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $227 per night (USD)VRBO
- From $91 per night (USD)
Expedia
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Leeward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $91 per night (USD)Expedia
- From $456 per night (USD)
VRBO
Bright condo with private hot tub - amazing walkable locale
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $456 per night (USD)VRBO
- From $429 per night (USD)
Expedia
**CONCH GET ENOUGH at The Truman Annex in Key West**
- Bedrooms:
- 3
- 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 $429 per night (USD)Expedia
- From $2000 per night (USD)
VRBO
Key West Oasis - Truman Annex Estate
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2000 per night (USD)VRBO
- From $185 per night (USD)
Expedia
Modern 2BR Condo Old Town\/Balcony & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action ...
From $185 per night (USD)Expedia
- From $404 per night (USD)
VRBO
Green Goddess - 4 BD\/3 BA Amazing 360 Degree 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 $404 per night (USD)VRBO
- From $148 per night (USD)
Expedia
Lil' Bit | Adorable Cottage on Quiet Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This classic "conch" home is modern ...
From $148 per night (USD)Expedia
- From $691 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
OVERVIEW The Cigar House is a 100+ year old“Cigar maker’s house”. The recently completely renovated house is charming, ...
From $691 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Duval Dream Loft by Brightwild | Right 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! This un ...
From $465 per night (USD)Expedia
- From $537 per night (USD)
VRBO
The Collins on Duval by Brightwild
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $537 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Fairway Villa w\/ Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $202 per night (USD)Expedia
- From $520 per night (USD)
VRBO
Sky Suite on Duval by Brightwild | Condo w\/Balcony
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $520 per night (USD)VRBO
- From $1066 per night (USD)
Expedia
**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 $1066 per night (USD)Expedia
- From $691 per night (USD)
VRBO
Old Town Key West Historic Cigarmaker's Cottage - 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 $691 per night (USD)VRBO
- From $482 per night (USD)
Expedia
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $482 per night (USD)Expedia
- From $994 per night (USD)
VRBO
Duval's Duet on Duval by Brightwild
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $994 per night (USD)VRBO
- From $3942 per night (USD)
Expedia
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
- Bedrooms:
- 15
- Bathrooms:
- 13
- Sleeps:
- 32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $3942 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Central walk-up studio with partial ac - walk to Duval Street bars\/dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Truman @ Duval - Unit E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $135 per night (USD)VRBO
- From $1251 per night (USD)
Expedia
**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 $1251 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Old Town home a short walk to Duval\/Couples Oasis
- Bedrooms:
- 2
- 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 $282 per night (USD)VRBO
- From $182 per night (USD)
Expedia
Relaxing island home\/Great location\/Stylish
- Bedrooms:
- 2
- 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 $182 per night (USD)Expedia
- From $369 per night (USD)
VRBO
NEW! Completely Renovated \/ Close to Everything
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the Heart of Historic Old Town Monthly Rental Pet Friendly. Up to 2 dogs, 40 lbs. max each. La Cala is a ...
From $369 per night (USD)VRBO
- From $792 per night (USD)
Expedia
MILLIONAIRES ROW GREAT PRICES 4 BR, pool, free Wi-Fi, convenient to Duval St.
- Bedrooms:
- 3
- 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 $792 per night (USD)Expedia
- Click For Pricing
VRBO
A BIT OF AQUA at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Foundry a Bostonian style, 3 level townhouses that have been refurbished with tropical flair. Vaulted cei ...
Click For PricingVRBO
- From $133 per night (USD)
Expedia
The Emelina, Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $133 per night (USD)Expedia
- From $252 per night (USD)
VRBO
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 $252 per night (USD)VRBO
- From $303 per night (USD)
Expedia
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 $303 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w\/ Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $185 per night (USD)VRBO
- From $202 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 $202 per night (USD)Expedia
- From $500 per night (USD)
VRBO
ISLAND OASIS at the Truman Annex in Key West
- Bedrooms:
- 3
- 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 $500 per night (USD)VRBO
- From $451 per night (USD)
Expedia
Sea Esta Suite by Brightwild | Pool on Duval
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - In the middle of Duval Street and walking distance to the Southernmost Point! - Bright & airy two-story townh ...
From $451 per night (USD)Expedia
- From $151 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
- 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 $151 per night (USD)VRBO
- From $157 per night (USD)
Expedia
Conch Cottage by Brightwild | Quiet w\/ Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go o ...
From $157 per night (USD)Expedia
- From $600 per night (USD)
VRBO
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 $600 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Yellow Room at Grand Maloney by Brightwild
- 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 $237 per night (USD)Expedia
- From $322 per night (USD)
VRBO
Blue Room at the Grand Maloney by Brightwild
- 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 $322 per night (USD)VRBO
- From $352 per night (USD)
Expedia
Green Room at the Grand Maloney by Brightwild
- 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 $352 per night (USD)Expedia
- Click For Pricing
Expedia
Home Away From Home-Beautiful Duval Duplex
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Come stay in paradise! Golf cart available for rent! We are perfectly located one block from Duval Street but in a tranq ...
Click For PricingExpedia
- From $381 per night (USD)
Expedia
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 $381 per night (USD)Expedia
- From $323 per night (USD)
VRBO
Duval Street Suite on Duval Free Parking and 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 $323 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Duval Street Suite full kitchen, parking, & 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 $338 per night (USD)Expedia
- From $333 per night (USD)
VRBO
Duval Street Suites full kitchen, parking, 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 $333 per night (USD)VRBO
- From $280 per night (USD)
Expedia
Duval Street Suite full kitchen and pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlookin ...
From $280 per night (USD)Expedia
- From $311 per night (USD)
VRBO
Duval Street Suite with full kitchen pool, parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duv ...
From $311 per night (USD)VRBO
- From $2862 per night (USD)
Expedia
6 BR 6 BA Guesthouse Suites on Duval parking, 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 $2862 per night (USD)Expedia
- From $329 per night (USD)
VRBO
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 $329 per night (USD)VRBO
- From $399 per night (USD)
Expedia
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 $399 per night (USD)Expedia
- From $643 per night (USD)
VRBO
VILLA AZURA THE BEST place to be in Key West!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Villa Azura - this is Enjoy this gem on a quiet lane in the award-winning gated community of the Truman An ...
From $643 per night (USD)VRBO
- From $200 per night (USD)
Expedia
MONTHLY RENTAL, Old Town, Duplex, newly renovated, private backyard
- 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 $200 per night (USD)Expedia
- From $336 per night (USD)
VRBO
Poolside Suite by Brightwild | Pvt Pool & Parking
- 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 $336 per night (USD)VRBO
- From $307 per night (USD)
Expedia
AWAY FROM IT ALL at The Truman Annex in Key West
- 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 $307 per night (USD)Expedia
- From $525 per night (USD)
VRBO
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 $525 per night (USD)VRBO
- From $1485 per night (USD)
Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1485 per night (USD)Expedia
- From $905 per night (USD)
VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 4
- 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 $905 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $287 per night (USD)Expedia
- From $281 per night (USD)
VRBO
Pool View & Pvt Balcony | Samana Cay Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $281 per night (USD)VRBO
- From $345 per night (USD)
Expedia
The Grand Turk by Brightwild | Sunset View & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the fun-filled Sunrise Suites complex located on the quiet side of Key West. - Just 1 mile from th ...
From $345 per night (USD)Expedia
- From $318 per night (USD)
VRBO
Duval Street Suite full kitchen Old Town with 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 $318 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Historic Caroline Street Condo!1 Bedroom 2 Bath, Pool, Amazing Old Town Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history ...
From $275 per night (USD)Expedia
- From $452 per night (USD)
VRBO
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Where the Ocean Meets the Windswept is nothing like . You don't have to spend a fortune to enjoy a spacious, clean and ...
From $452 per night (USD)VRBO
- From $409 per night (USD)
Expedia
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Caribbean Conch is a fantastic rental with a great location close to the pool. This unit features an extra large floor p ...
From $409 per night (USD)Expedia