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

From $495 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 $495 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 $458 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 $458 per night (USD)
Expedia
From $185 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 $185 per night (USD)
VRBO
From $940 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 $940 per night (USD)
Expedia
From $2101 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 $2101 per night (USD)
VRBO
From $796 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 $796 per night (USD)
Expedia
From $828 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 $828 per night (USD)
VRBO
From $674 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 $674 per night (USD)
Expedia
From $775 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 $775 per night (USD)
VRBO
$Fairway Villa w\/ Private Pool$
From $353 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 $353 per night (USD)
Expedia
From $656 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 $656 per night (USD)
VRBO
From $5126 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 $5126 per night (USD)
Expedia
$Central walk-up studio with partial ac - walk to Duval Street bars\/dining$
Click For Pricing
VRBO
Central walk-up studio with partial ac - walk to Duval Street bars\/dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman at Duval - Unit E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
VRBO
From $1587 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 $1587 per night (USD)
Expedia
From $2055 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 $2055 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 $771 per night (USD)
Expedia
5 STAR yet low rates. 3 BR + 1 BR cottage, private pool, close to Duval.
Bedrooms:
4
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 $771 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 $555 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 $555 per night (USD)
Expedia
$COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen & Shared Pool!$
From $428 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 $428 per night (USD)
VRBO
$ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w\/ Kitchen and Shared Pool!$
From $532 per night (USD)
Expedia
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 $532 per night (USD)
Expedia
From $564 per night (USD)
VRBO
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 $564 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
From $184 per night (USD)
VRBO
NEW MONTHLY RENTAL, Old Town, Duplex, JUNE OPEN, 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 $184 per night (USD)
VRBO
$Conch Cottage | 'Old Town' Home w\/ Shared Pool$
From $181 per night (USD)
Expedia
Conch Cottage | 'Old Town' Home w\/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this charming Key West cottage, the perfect home base for your island getaway. Whether you relax by t ...
From $181 per night (USD)
Expedia
$Charming 'Boho Breeze' Retreat w\/ Pool Access$
From $217 per night (USD)
VRBO
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 $217 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 $353 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 $353 per night (USD)
VRBO
From $514 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 $514 per night (USD)
Expedia
From $417 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 $417 per night (USD)
VRBO
From $497 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 $497 per night (USD)
Expedia
From $407 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 $407 per night (USD)
VRBO
From $630 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 $630 per night (USD)
Expedia
From $247 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 $247 per night (USD)
VRBO
From $450 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 $450 per night (USD)
Expedia
From $271 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 $271 per night (USD)
VRBO
From $422 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 $422 per night (USD)
Expedia
From $431 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 $431 per night (USD)
VRBO
From $2006 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 $2006 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 $724 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 $724 per night (USD)
Expedia
From $364 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 $364 per night (USD)
VRBO
From $605 per night (USD)
Expedia
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 $605 per night (USD)
Expedia
From $1843 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 $1843 per night (USD)
VRBO
From $1238 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 $1238 per night (USD)
Expedia
$Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio at Mile Marker 0!$
From $362 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 $362 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 $589 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 $589 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $572 per night (USD)
VRBO
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $572 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $603 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 $313 per night (USD)
Expedia
Rent a Piece of Paradise, Best Location on the Island!
Bedrooms:
2
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 $313 per night (USD)
Expedia
From $502 per night (USD)
VRBO
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 $502 per night (USD)
VRBO
From $413 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 $413 per night (USD)
Expedia
From $401 per night (USD)
VRBO
**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 $401 per night (USD)
VRBO
From $670 per night (USD)
Expedia
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 $670 per night (USD)
Expedia
From $1144 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 $1144 per night (USD)
VRBO
From $564 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 $564 per night (USD)
Expedia
$Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi$
From $450 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 $450 per night (USD)
VRBO
From $225 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 $225 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $1836 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 $1836 per night (USD)
Expedia
From $580 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 $580 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 $473 per night (USD)
VRBO
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)
VRBO
From $1537 per night (USD)
Expedia
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 $1537 per night (USD)
Expedia
From $164 per night (USD)
VRBO
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 $164 per night (USD)
VRBO
From $240 per night (USD)
Expedia
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 $240 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 at Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
VRBO
From $734 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 $734 per night (USD)
Expedia
From $742 per night (USD)
VRBO
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 $742 per night (USD)
VRBO
$**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…$
From $3032 per night (USD)
Expedia
**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 $3032 per night (USD)
Expedia
From $216 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 $216 per night (USD)
VRBO
From $255 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 $255 per night (USD)
VRBO
From $1448 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 $1448 per night (USD)
VRBO
From $2522 per night (USD)
Expedia
Banana's Foster Guesthouse | 1 Block to Duval St
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 $2522 per night (USD)
Expedia
From $437 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 $437 per night (USD)
VRBO
From $357 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 $357 per night (USD)
Expedia
From $313 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 $313 per night (USD)
VRBO
From $883 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 $883 per night (USD)
VRBO
From $294 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 $294 per night (USD)
VRBO
From $329 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 $329 per night (USD)
VRBO
From $273 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 $273 per night (USD)
VRBO
From $246 per night (USD)
Expedia
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $246 per night (USD)
Expedia
From $1419 per night (USD)
VRBO
Poolside Paradise | Heated Pool, Steps to Duval St!
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 $1419 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Poolside Retreat | Shared Heated Pool, Near Duval
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 $486 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 $1521 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 $1521 per night (USD)
VRBO
From $533 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 $533 per night (USD)
VRBO
$Sea Breeze Cottage 2 Large Decks, pool, free parking\/wifi in Truman Annex$
From $506 per night (USD)
Expedia
Sea Breeze Cottage 2 Large Decks, pool, free parking\/wifi in 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. This is ...
From $506 per night (USD)
Expedia
From $404 per night (USD)
VRBO
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $404 per night (USD)
VRBO
From $544 per night (USD)
Expedia
'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Histo ...
From $544 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $437 per night (USD)
VRBO
Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
Expedia

Search Your Destination Now!

Key West Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals