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 $635 per night (USD)
VRBO
Historic Inn: Romantic Couple Stay in Key West's Hidden Gem - Pools & Patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $635 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $453 per night (USD)
Expedia
From $660 per night (USD)
VRBO
Palms and Pool Paradise
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious Key West retreat in the heart of midtown! This spacious house boasts a private pool, soothing h ...
From $660 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Escape to the Keys! Modern Pet-friendly Unit! EV Charger and Parking! 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 $350 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Tropical Dream! Pool, Restaurant, Bar, Gym, Bike Rental, Parking!
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 $296 per night (USD)
VRBO
$Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches$
From $196 per night (USD)
Expedia
Seaside Serenity-2BD 2BA condo w\/ pool, parking, tennis courts, near beaches
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 $196 per night (USD)
Expedia
From $1674 per night (USD)
VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1674 per night (USD)
VRBO
From $594 per night (USD)
VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $594 per night (USD)
VRBO
From $486 per night (USD)
VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $486 per night (USD)
VRBO
From $610 per night (USD)
VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $610 per night (USD)
VRBO
From $764 per night (USD)
VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $764 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $480 per night (USD)
VRBO
From $791 per night (USD)
VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $791 per night (USD)
VRBO
From $594 per night (USD)
VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $594 per night (USD)
VRBO
From $486 per night (USD)
VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $486 per night (USD)
VRBO
From $1256 per night (USD)
VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1256 per night (USD)
VRBO
From $2052 per night (USD)
VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2052 per night (USD)
VRBO
From $843 per night (USD)
VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $843 per night (USD)
VRBO
From $655 per night (USD)
VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $655 per night (USD)
VRBO
From $1405 per night (USD)
VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1405 per night (USD)
VRBO
From $568 per night (USD)
VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation Fun!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $568 per night (USD)
VRBO
From $937 per night (USD)
VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $937 per night (USD)
VRBO
From $1295 per night (USD)
VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1295 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $522 per night (USD)
VRBO
From $596 per night (USD)
VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $596 per night (USD)
VRBO
From $422 per night (USD)
VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $422 per night (USD)
VRBO
From $711 per night (USD)
VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $711 per night (USD)
VRBO
From $663 per night (USD)
VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $663 per night (USD)
VRBO
From $729 per night (USD)
VRBO
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $729 per night (USD)
VRBO
From $1830 per night (USD)
VRBO
4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1830 per night (USD)
VRBO
From $2052 per night (USD)
VRBO
3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2052 per night (USD)
VRBO
From $988 per night (USD)
Expedia
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $988 per night (USD)
Expedia
From $1373 per night (USD)
VRBO
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1373 per night (USD)
VRBO
$Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D$
Click For Pricing
Expedia
Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Key to Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
Expedia
From $201 per night (USD)
VRBO
Beautifully Renovated Paradise with Pool and Tropical Gardens in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into paradise in this clean and impeccably appointed 2 bedroom, 2 bathroom house in Old Town. Located just 2 blocks ...
From $201 per night (USD)
VRBO
From $415 per night (USD)
Expedia
Bohemian Retreat with Pool in Old Town Key West | Walk to Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $415 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $672 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Lofted 1 bedroom suite right off Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to sweet paradise! Located on Petronia Street, the Orange Blossom Suite is in close proximity to all the fun-fil ...
From $316 per night (USD)
Expedia
$Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking$
From $184 per night (USD)
VRBO
Southard Retreat- 2 bed 2 bath townhome downtown w\/ pool, parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $184 per night (USD)
VRBO
$Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent$
From $256 per night (USD)
Expedia
Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent
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 $256 per night (USD)
Expedia
$4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview$
From $298 per night (USD)
VRBO
4 bed 2.5 bath home w\/ ocean views, private pool oasis on Gulfview
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $298 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Royal Palm in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Truman Annex Properties are going to Monthly (or longer) rentals beginning January 1, 2026 because of changing licensing ...
From $379 per night (USD)
Expedia
$Key West Home on Golf Course w\/ Patio & Grill!$
From $258 per night (USD)
VRBO
Key West Home on Golf Course w\/ Patio & Grill!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Play a round of golf, snorkel the crystal-clear waters, and explore Key West’s bustling downtown when you stay at this l ...
From $258 per night (USD)
VRBO
From $445 per night (USD)
Expedia
A Gulfview Paradise in Key West - Call for more information!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Welcome to your dream vacation rental in Gulfview Pointe, Key West! This stunning property offers breathtaking waterfron ...
From $445 per night (USD)
Expedia
From $1711 per night (USD)
VRBO
Private Parking & Pool - The Delaney House
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Step into the classic conch cottage known as the Delaney House, situated just half a block from Duval Street. ...
From $1711 per night (USD)
VRBO
From $185 per night (USD)
Expedia
A Sunkissed Bungalow-B205
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A perfect beach getaway in Key West! See the Sunset and stroll the sidewalks at this fabulous location away from the cr ...
From $185 per night (USD)
Expedia
From $178 per night (USD)
VRBO
A Kokomo Cottage: 3 BR, 2 BA Condominium in Key West, Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...
From $178 per night (USD)
VRBO
From $178 per night (USD)
Expedia
A Sandy Toes Retreat-A310
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautifully renovated 3 bedroom, 2 bathroom beach getaway is waiting for your perfect escape. See the Sunset and s ...
From $178 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Tropical cottage with private pool, two blocks from Duval - near Hemingway House
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
The Conch-Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $192 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Boomerang Boathouse in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Richley individual yet classic Key West are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with ...
From $360 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $228 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $228 per night (USD)
Expedia
$Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town$
From $258 per night (USD)
VRBO
Newly Renovated Hotel w\/ Outdoor Pool | Short Drive to Historic Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $258 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $258 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Balcony on Duval - The Green Pineapple
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: Beautiful 3-bedroom, 2-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access ...
From $359 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Pool, Pet Friendly, & Near Duval - Coastal Rose
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $566 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Pet Friendly, Near Duval - Rose Petal Petite Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $379 per night (USD)
VRBO
From $950 per night (USD)
Expedia
Pet Friendly, & Near Duval - Rose Key Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $950 per night (USD)
Expedia
From $298 per night (USD)
VRBO
An Island Siesta: 2 BR, 2 BA Townhouse in Key West, Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $298 per night (USD)
VRBO
From $535 per night (USD)
Expedia
Atlantis House's Banyan Suite-voted top 25 in USA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Banyan Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situat ...
From $535 per night (USD)
Expedia
From $606 per night (USD)
VRBO
Atlantis House's Palm Suite-voted top 25 in USA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Palm Suite is a stunning vacation rental property located in the heart of Key West. This luxurious suite is situated ...
From $606 per night (USD)
VRBO
Click For Pricing
Expedia
Keys to Paradise by AvantStay | Balcony, Pool, Golf
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home is available for stays of 28 nights or longer. Welcome to Keys to Paradise, your Key West sanctuary nestled r ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Upgraded 2-Bedroom Condo-Olympic size Pool- Fitness room-Beach-on Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful upgraded condo features vaulted ceilings and spacious living room, two bedrooms and a office/den for your use. ...
Click For Pricing
VRBO
$SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!$
From $388 per night (USD)
Expedia
SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
AUTHENTIC KEY WEST AMBIENCE... This fully renovated mid-century jewel pairs modern allure with classic White Street Gall ...
From $388 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Speakeasy Inn-Room 3B- 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $447 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five ...
From $229 per night (USD)
Expedia
From $337 per night (USD)
VRBO
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CLASSIC CHARMER... Some of the best things come in small packages and this conch cutie is no exception. Nestled in the e ...
From $337 per night (USD)
VRBO
From $919 per night (USD)
Expedia
An Ocean Serenity in Truman Annex, Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award ...
From $919 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $513 per night (USD)
VRBO
$Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun$
From $404 per night (USD)
Expedia
Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $404 per night (USD)
Expedia
$2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums$
From $806 per night (USD)
VRBO
2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $806 per night (USD)
VRBO
$2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West$
From $752 per night (USD)
Expedia
2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $752 per night (USD)
Expedia
From $1461 per night (USD)
VRBO
The Lighthouse Penthouse Suite
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape the Ordinary... The Lighthouse Penthouse Suite is a combination of two 1 BD/ 1 BA Suites delivering two luxury k ...
From $1461 per night (USD)
VRBO
From $1858 per night (USD)
Expedia
The Lighthouse Group Suite
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Escape the Ordinary... The Lighthouse Group Suite is a combination of two 2 BD/ 1 BA Suites delivering two luxury king ...
From $1858 per night (USD)
Expedia
$Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar$
From $464 per night (USD)
VRBO
Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $464 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Charming 2-bedroom House in Historic Key West with Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Embrace the Enchantment of Old Key West Charm! Escape to the enchanting world of Key West Hideaway, where history meets ...
From $196 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $199 per night (USD)
VRBO
From $516 per night (USD)
Expedia
Heron Hideaway - Charming 1st-Floor Unit, Shared Pool, Private Hot Tub, Near Duval St & Beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $516 per night (USD)
Expedia
$Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental$
From $225 per night (USD)
VRBO
Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental
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 $225 per night (USD)
VRBO
From $2028 per night (USD)
Expedia
Pool & Parking, & Near Duval - The Rigby House
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $2028 per night (USD)
Expedia
From $681 per night (USD)
VRBO
NEW!!! Gorgeous! Beacon Terrace in the Truman Annex Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
"Beacon Terrace" in the Truman Annex is a beautifully renovated town home in the historic Foundry in the Truman Annex. ...
From $681 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Tropical Tee Time Villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to a stunning vacation rental in Key West, nestled on a picturesque golf course within an amazing resort. This pr ...
From $347 per night (USD)
Expedia
From $1228 per night (USD)
VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1228 per night (USD)
VRBO
From $655 per night (USD)
Expedia
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $655 per night (USD)
Expedia
$Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away$
From $372 per night (USD)
VRBO
Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $372 per night (USD)
VRBO
From $1127 per night (USD)
Expedia
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $1127 per night (USD)
Expedia
$Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval$
From $1238 per night (USD)
VRBO
Charming 2 room guest house, access to Pool, A\/C, & WiFi, Key West, near Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Key West is waiting for you at this clean & spacious 2-bedroom guest house. Good for up to 6 people. This cozy retreat o ...
From $1238 per night (USD)
VRBO
From $2425 per night (USD)
Expedia
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city the ...
From $2425 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Contemporary Hideaway in the Heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. E ...
From $152 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Stunning 2BD Oceanfront Escape, Breathtaking Views - pool, hot tub and more
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Côte du Bonheur, your oceanfront retreat located in Key West. This 3rd Floor-level unit in the prestigious 18 ...
From $494 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Atlantis House- beautiful residence close to beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to the Atlantis House, a beautiful vacation rental located in the heart of the charming island town of Key West. ...
From $674 per night (USD)
VRBO
From $1092 per night (USD)
Expedia
Charming Bungalow Perfect for Families and Couples': Escape in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1092 per night (USD)
Expedia
From $909 per night (USD)
VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $909 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $380 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Charming 1-bedroom apartment with WiFi, AC in delightful Key West Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Key West adventure begins at this fabulous 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for ...
From $203 per night (USD)
VRBO
From $417 per night (USD)
Expedia
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $417 per night (USD)
Expedia
From $125 per night (USD)
VRBO
Serene Key West Studio with Poolside Peace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $125 per night (USD)
VRBO
From $660 per night (USD)
Expedia
3-bedroom townhome in Key West with fitness room, WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $660 per night (USD)
Expedia
From $823 per night (USD)
VRBO
Atlantis House Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled within the serene enclave of the Atlantis House Compound, the Palm and Banyan Suites offer a tropical oasis for ...
From $823 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Coco's Poolside Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Coco's Poolside Retreat is a 3-story Key West vacation rental townhouse situated in a one-of-a-kind private tropical poo ...
From $716 per night (USD)
Expedia

Search Your Destination Now!

Key West Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals