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

Key West Rentals

Filter

Popular Areas

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 Pricing
VRBO
From $1108 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 $1108 per night (USD)
Expedia
From $686 per night (USD)
VRBO
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 $686 per night (USD)
VRBO
From $912 per night (USD)
Expedia
Bright condo with charms of historic Key West - amazing walkable locale
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $912 per night (USD)
Expedia
From $543 per night (USD)
VRBO
**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 $543 per night (USD)
VRBO
From $2397 per night (USD)
Expedia
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 $2397 per night (USD)
Expedia
$Modern 2BR Condo Old Town\/Balcony & Pool$
From $194 per night (USD)
VRBO
Modern 2BR Condo Old Town\/Balcony & Pool
Bedrooms:
2
Bathrooms:
3
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 $194 per night (USD)
VRBO
$Green Goddess - 4 BD\/3 BA Amazing 360 Degree Rooftop Views! RealKeyWest$
From $644 per night (USD)
Expedia
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 $644 per night (USD)
Expedia
From $189 per night (USD)
VRBO
Private Parking & Near Downtown - Lil' Bit
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This classic "conch" home is modern ...
From $189 per night (USD)
VRBO
From $1180 per night (USD)
Expedia
Balcony & Near Downtown - Sky Suite on Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $1180 per night (USD)
Expedia
From $2090 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 $2090 per night (USD)
VRBO
From $833 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, 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 $833 per night (USD)
Expedia
From $1005 per night (USD)
VRBO
Balcony on Duval - Duval Dream Loft
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $1005 per night (USD)
VRBO
From $1301 per night (USD)
Expedia
Balcony on Duval - The Collins on Duval
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $1301 per night (USD)
Expedia
From $833 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Conch House, Sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $833 per night (USD)
VRBO
$Fairway Villa w\/ Private Pool$
From $431 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 $431 per night (USD)
Expedia
From $805 per night (USD)
VRBO
**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 $805 per night (USD)
VRBO
From $4736 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 $4736 per night (USD)
Expedia
$Central walk-up studio with partial ac - walk to Duval Street bars\/dining$
From $459 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 $459 per night (USD)
VRBO
From $1797 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 $1797 per night (USD)
Expedia
From $2816 per night (USD)
VRBO
Balcony on Duval - Duval's Duet on Duval
Bedrooms:
2
Bathrooms:
6
Sleeps:
18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $2816 per night (USD)
VRBO
$Old Town home a short walk to Duval\/Couples Oasis$
From $301 per night (USD)
Expedia
Old Town home a short walk to Duval\/Couples Oasis
Bedrooms:
2
Bathrooms:
2
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
$Relaxing island home\/Great location\/Stylish$
From $253 per night (USD)
VRBO
Relaxing island home\/Great location\/Stylish
Bedrooms:
2
Bathrooms:
2
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 $1192 per night (USD)
Expedia
MILLIONAIRES ROW GREAT PRICES 4 BR, pool, free Wi-Fi, convenient to Duval St.
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Our calendar is updated in real time and our rates are accurately displayed. You can book instantly without waiting for ...
From $1192 per night (USD)
Expedia
From $394 per night (USD)
VRBO
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 $394 per night (USD)
VRBO
$SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $561 per night (USD)
Expedia
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $561 per night (USD)
Expedia
$COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!$
From $565 per night (USD)
VRBO
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $565 per night (USD)
VRBO
$Charming 'Boho Breeze' Retreat w\/ Pool Access$
From $168 per night (USD)
Expedia
Charming 'Boho Breeze' Retreat w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $168 per night (USD)
Expedia
$ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $632 per night (USD)
VRBO
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $632 per night (USD)
VRBO
From $620 per night (USD)
Expedia
ISLAND OASIS in the Truman Annex
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 $620 per night (USD)
Expedia
Click For Pricing
VRBO
Private Balcony & Parking - Sea Esta Suite
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: - In the middle of Duval Street and walking distance to the Southernmost Point! - Bright & airy two-story townh ...
Click For Pricing
VRBO
From $180 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
Bedrooms:
2
Bathrooms:
3
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 $180 per night (USD)
Expedia
$Conch Cottage | 'Old Town' Home w\/ Shared Pool$
From $249 per night (USD)
VRBO
Conch Cottage | 'Old Town' Home 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 $249 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
4
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 $460 per night (USD)
VRBO
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 $460 per night (USD)
VRBO
From $661 per night (USD)
Expedia
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 $661 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Green Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
2
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 $572 per night (USD)
VRBO
From $630 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 $630 per night (USD)
Expedia
From $562 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 $562 per night (USD)
VRBO
From $798 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 $798 per night (USD)
Expedia
From $566 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 $566 per night (USD)
VRBO
From $571 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 $571 per night (USD)
Expedia
From $529 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 $529 per night (USD)
VRBO
From $506 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 (queen) and kitchen. Overlookin ...
From $506 per night (USD)
Expedia
From $492 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 (queen) and kitchen. Overlooking Duv ...
From $492 per night (USD)
VRBO
From $1934 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 $1934 per night (USD)
Expedia
$MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA$
From $183 per night (USD)
VRBO
MONTHLY RENTAL, Old Town, Duplex, private yard, 2 BR\/2 BA
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 $183 per night (USD)
VRBO
From $941 per night (USD)
Expedia
Parking & Near Duval - Poolside Suite
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $941 per night (USD)
Expedia
From $399 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 $399 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Galleon Resort beach hotel luxury in Old Town Key West
Bedrooms:
1
Bathrooms:
2
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)
VRBO
From $2191 per night (USD)
VRBO
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 $2191 per night (USD)
VRBO
From $1365 per night (USD)
Expedia
**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 $1365 per night (USD)
Expedia
$Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!$
From $357 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)
VRBO
Click For Pricing
Expedia
Balcony, Pool, & Pet Friendly - Samana Cay Suite
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
Click For Pricing
Expedia
From $779 per night (USD)
VRBO
Balcony, Pool, & Pet Friendly - The Grand Turk
Bedrooms:
2
Bathrooms:
3
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 $779 per night (USD)
VRBO
From $504 per night (USD)
Expedia
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 $504 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
3
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 $619 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Caribbean Conch is a fantastic rental with a prime location near the pool. This unit features an extra-large floor plan, ...
From $658 per night (USD)
Expedia
Click For Pricing
VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For Pricing
VRBO
From $808 per night (USD)
Expedia
Balcony, Pool, & Pet Friendly - The Trinidad
Bedrooms:
2
Bathrooms:
3
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 $808 per night (USD)
Expedia
From $615 per night (USD)
VRBO
Rent a Piece of Paradise, Best Location on the Island!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $615 per night (USD)
VRBO
From $503 per night (USD)
Expedia
The Palms...A beautiful space in the perfect place.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $503 per night (USD)
Expedia
From $740 per night (USD)
VRBO
A BANANA REPUBLIC in Old Town Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $740 per night (USD)
VRBO
From $410 per night (USD)
Expedia
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For a month i ...
From $410 per night (USD)
Expedia
From $1256 per night (USD)
VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + 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! Throughout Ke ...
From $1256 per night (USD)
VRBO
From $778 per night (USD)
Expedia
Balcony, Pool, & Pet Friendly - The Barbados
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $778 per night (USD)
Expedia
$Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi$
From $726 per night (USD)
VRBO
Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $726 per night (USD)
VRBO
From $217 per night (USD)
Expedia
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience elegant sophistication in this stunning 2-bedroom, 2-bathroom ocean-view condominium at the premier 1800 Atla ...
From $217 per night (USD)
Expedia
From $300 per night (USD)
VRBO
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $300 per night (USD)
VRBO
From $2091 per night (USD)
Expedia
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2091 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $473 per night (USD)
VRBO
$Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar$
From $587 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $587 per night (USD)
Expedia
Click For Pricing
VRBO
Balcony, Pool, & Pet Friendly - The Andros
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
Click For Pricing
VRBO
From $566 per night (USD)
Expedia
Happy’s Houseboat Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $566 per night (USD)
Expedia
From $260 per night (USD)
VRBO
Private Paradise with Heated Waterfall Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $260 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Bohemian Breeze @ Truman Annex
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $473 per night (USD)
Expedia
From $2340 per night (USD)
VRBO
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $2340 per night (USD)
VRBO
From $188 per night (USD)
Expedia
Centrally located cottage apartment with patio - walk to beach & dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $188 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy condo with free WiFi & fantastic location in central Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman @ Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
VRBO
From $708 per night (USD)
Expedia
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $708 per night (USD)
Expedia
From $282 per night (USD)
VRBO
A+ Location in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $282 per night (USD)
VRBO
From $901 per night (USD)
Expedia
AFTERNOON DELIGHT at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $901 per night (USD)
Expedia
$**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…$
From $3369 per night (USD)
VRBO
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
10
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $3369 per night (USD)
VRBO
From $269 per night (USD)
VRBO
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $269 per night (USD)
VRBO
From $1499 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1499 per night (USD)
VRBO
From $5013 per night (USD)
Expedia
Balcony, & Pool, Near Duval - Bananas Foster
Bedrooms:
8
Bathrooms:
9
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $5013 per night (USD)
Expedia
From $510 per night (USD)
VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $510 per night (USD)
VRBO
From $365 per night (USD)
Expedia
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $365 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $356 per night (USD)
VRBO
From $1196 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1196 per night (USD)
VRBO
From $399 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $399 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $452 per night (USD)
VRBO
From $387 per night (USD)
VRBO
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $387 per night (USD)
VRBO
From $262 per night (USD)
Expedia
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This freshly ...
From $262 per night (USD)
Expedia
From $1591 per night (USD)
VRBO
Pool & Parking, Near Duval - Poolside Paradise
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1591 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Pet Friendly, & Near Duval - Poolside Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $540 per night (USD)
Expedia
Click For Pricing
VRBO
Updated home with private pool, patio, & grill in enclosed tropical backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
VRBO
From $1780 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1780 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $480 per night (USD)
VRBO
From $585 per night (USD)
Expedia
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. 3 bedro ...
From $585 per night (USD)
Expedia

Search Your Destination Now!

Key West Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals