Key West Rentals
From $430 per night (USD)VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Midnight Cowboy by AvantStay! *Please note that this home is available for 28+ night stays only.* Midnight ...
From $430 per night (USD)VRBO
From $212 per night (USD)Expedia
Historic Old Town Oasis • Pool + Walk to Duval Street | Monkey House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Monkey House is a one-of-a-kind Key West escape whe ...
From $212 per night (USD)Expedia
From $232 per night (USD)VRBO
Tennessee Williams by AvantStay | Funky Design + Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $232 per night (USD)VRBO
From $652 per night (USD)Expedia
BE AS YOU ARE - 3 Bedroom / 3 Bathroom - Mid Town KEY WEST w/ POOL
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to “Be As You Are” – Your Perfect Key West Getaway Thoughtfully renovated and beautifully furnished with guest ...
From $652 per night (USD)Expedia
From $536 per night (USD)VRBO
Historic Key West Gem: Private Tiki Bar, 4 En Suites, Walk to Duval & Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, ...
From $536 per night (USD)VRBO
From $735 per night (USD)Expedia
KAMP - Rooftop Penthouse Overlooking Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "M ...
From $735 per night (USD)Expedia
From $261 per night (USD)VRBO
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Romantic Retreat is an Historic, free standing cottage which, in the 1800`s, was the cistern for the Cigar Maker cottage ...
From $261 per night (USD)VRBO
From $1328 per night (USD)Expedia
~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $1328 per night (USD)Expedia
From $320 per night (USD)VRBO
**THE COZY STARFISH @ THE ANNEX** Condo + Last Key White Glove Service...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! THE COZY STAR ...
From $320 per night (USD)VRBO
From $238 per night (USD)VRBO
Quaint Bungalow w/ Private Outdoor Space Near Duval Street | Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 270 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
From $382 per night (USD)VRBO
Celebrate History in Key West: Tropical Free Breakfast and Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 270 sq. ft, equipped with complimentary toiletries, high defi ...
From $382 per night (USD)VRBO
From $238 per night (USD)VRBO
Serene Bungalow with Outdoor Pool Access | Free Breakfast Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 312 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
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Romantic Getaway with Plush Turkish Robes & Inviting Pools! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This listing is for a room within a hotel. ✦ Your room is 270 sq. ft, equipped with complimentary toiletries, high defi ...
Click For PricingVRBO
From $238 per night (USD)VRBO
Serene Bungalow in Key West: Poolside Refreshers & Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 240 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
From $238 per night (USD)VRBO
Stylish Room in the Heart of Old Town w/ Access to Outdoor Pool | Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 312 sq. ft, equipped with complimentary toiletries, high defi ...
From $238 per night (USD)VRBO
From $319 per night (USD)VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 200 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $319 per night (USD)VRBO
From $204 per night (USD)VRBO
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 $204 per night (USD)VRBO
From $2128 per night (USD)VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $2128 per night (USD)VRBO
From $891 per night (USD)VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room equipped with complimentary toiletries, TV. ✦ Cleaning service ...
From $891 per night (USD)VRBO
From $600 per night (USD)VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room equipped with complimentary toiletries, TV. ✦ Cleaning service ...
From $600 per night (USD)VRBO
From $843 per night (USD)VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $843 per night (USD)VRBO
From $974 per night (USD)VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $974 per night (USD)VRBO
From $550 per night (USD)VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Pier House Resort & Spa at 1 Duval Street offers an island-chic escape with a private white-sand beach, full-service ...
From $550 per night (USD)VRBO
From $1252 per night (USD)VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $1252 per night (USD)VRBO
From $816 per night (USD)VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room equipped with complimentary toiletries, TV. ✦ Cleaning service ...
From $816 per night (USD)VRBO
From $600 per night (USD)VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room equipped with complimentary toiletries, TV. ✦ Cleaning service ...
From $600 per night (USD)VRBO
From $1595 per night (USD)VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $1595 per night (USD)VRBO
From $3025 per night (USD)VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $3025 per night (USD)VRBO
From $1054 per night (USD)VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $1054 per night (USD)VRBO
From $1008 per night (USD)VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $1008 per night (USD)VRBO
From $2013 per night (USD)VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $2013 per night (USD)VRBO
From $622 per night (USD)VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation Fun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $622 per night (USD)VRBO
From $1054 per night (USD)VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $1054 per night (USD)VRBO
From $2017 per night (USD)VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $2017 per night (USD)VRBO
From $550 per night (USD)VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Pier House Resort & Spa at 1 Duval Street offers an island-chic escape with a private white-sand beach, full-service ...
From $550 per night (USD)VRBO
From $627 per night (USD)VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $627 per night (USD)VRBO
From $527 per night (USD)VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $527 per night (USD)VRBO
From $999 per night (USD)VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $999 per night (USD)VRBO
From $843 per night (USD)VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $843 per night (USD)VRBO
From $974 per night (USD)VRBO
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $974 per night (USD)VRBO
From $2128 per night (USD)VRBO
4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $2128 per night (USD)VRBO
From $3025 per night (USD)VRBO
3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $3025 per night (USD)VRBO
From $1263 per night (USD)VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $1263 per night (USD)VRBO
From $1594 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
At 1 Duval Street, The Pier House Resort & Spa offers an island-chic retreat with a private white-sand beach, spa, dinin ...
From $1594 per night (USD)VRBO
From $581 per night (USD)VRBO
**GARDEN OF EMMA** Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Tranquility. ...
From $581 per night (USD)VRBO
From $293 per night (USD)VRBO
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 180 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $293 per night (USD)VRBO
From $419 per night (USD)VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 300 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $419 per night (USD)VRBO
From $174 per night (USD)Expedia
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 $174 per night (USD)Expedia
From $265 per night (USD)VRBO
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 $265 per night (USD)VRBO
From $283 per night (USD)Expedia
4 bed 2.5 bath home w/ ocean views, private pool oasis on Gulfview
- Bedrooms:
- 2
- 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 $283 per night (USD)Expedia
From $218 per night (USD)VRBO
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 $218 per night (USD)VRBO
From $271 per night (USD)Expedia
Old Town Proximity - Island Serenity!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the ultimate Key West lifestyle in this serene sanctuary overlooking the 8th hole of the Key West Golf Club. ...
From $271 per night (USD)Expedia
From $319 per night (USD)VRBO
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 $319 per night (USD)VRBO
From $398 per night (USD)Expedia
A KOKOMO COTTAGE-A311: 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 $398 per night (USD)Expedia
From $396 per night (USD)VRBO
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 $396 per night (USD)VRBO
From $388 per night (USD)Expedia
Boomerang Boathouse
- 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 w ...
From $388 per night (USD)Expedia
From $557 per night (USD)VRBO
Honeymoon Banyan Suite near Higgs Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Honeymoon Suite close to Higgs Beach The Space: The Banyan Suite is a stunning vacation rental property lo ...
From $557 per night (USD)VRBO
From $539 per night (USD)Expedia
Honeymoon Palm Suite near Higgs Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Honeymoon Suite close to Higgs Beach The Space: The Palm Suite is a stunning vacation rental property loca ...
From $539 per night (USD)Expedia
From $195 per night (USD)VRBO
Key West King Escape, Fairfield Inn, Outdoor Swimming Pool | Near Mallory Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and th ...
From $195 per night (USD)VRBO
From $195 per night (USD)VRBO
Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and th ...
From $195 per night (USD)VRBO
From $195 per night (USD)VRBO
Newly Renovated Hotel w/ Outdoor Pool | Short Drive to Historic Old Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and th ...
From $195 per night (USD)VRBO
From $195 per night (USD)VRBO
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located just 1.8 miles from Key West International Airport, enjoy easy access to Duval Street’s vibrant nightlife and th ...
From $195 per night (USD)VRBO
From $544 per night (USD)VRBO
Coastal Rose - Private Pool & Near Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared poo ...
From $544 per night (USD)VRBO
From $944 per night (USD)Expedia
Rose Key Cottage - Private Pool & Near Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in ...
From $944 per night (USD)Expedia
From $380 per night (USD)VRBO
AN ISLAND SIESTA: 2 BR, 2 BA Townhouse in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $380 per night (USD)VRBO
From $485 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 $485 per night (USD)Expedia
From $412 per night (USD)VRBO
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 $412 per night (USD)VRBO
From $290 per night (USD)Expedia
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $290 per night (USD)Expedia
From $944 per night (USD)VRBO
An Ocean Serenity at the Truman Annex in Key West
- Bedrooms:
- 2
- 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 $944 per night (USD)VRBO
From $347 per night (USD)VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Pool, Free Breakfast
- 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 $347 per night (USD)VRBO
From $262 per night (USD)VRBO
Old Town Conch Cottage - Full Kitchen, New A/C, Refreshing Pool & Bikes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Settle into authentic Old Town Key West with an extended monthly stay in this historic 1928 Conch cottage, quietly tucke ...
From $262 per night (USD)VRBO
From $238 per night (USD)VRBO
Modern Lodge with Outdoor Pool Access & Near Attractions!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 420 sq. ft, equipped with complimentary toiletries, standard ...
From $238 per night (USD)VRBO
From $474 per night (USD)VRBO
2 Rooms for the whole family w/ Pool Access & Near Museums!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $474 per night (USD)VRBO
From $323 per night (USD)VRBO
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a room within a hotel. ✦ Your room is 800 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $323 per night (USD)VRBO
From $319 per night (USD)VRBO
Stylish Boutique Room w/ 2 Queen Beds - Access Pool & Poolside Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 360 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $319 per night (USD)VRBO
From $209 per night (USD)Expedia
Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!
- Bedrooms:
- 1
- 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 $209 per night (USD)Expedia
From $224 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 $224 per night (USD)VRBO
From $1201 per night (USD)Expedia
Knowles Guest House w/Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Your group will be close to everything when you stay at this centrally-located home in Key West. The Space: ...
From $1201 per night (USD)Expedia
From $1968 per night (USD)VRBO
Knowles Main House with Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Your group will be close to everything when you stay at this centrally-located home in Key West. This listing ...
From $1968 per night (USD)VRBO
From $845 per night (USD)VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 900 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $845 per night (USD)VRBO
From $731 per night (USD)VRBO
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $731 per night (USD)VRBO
From $445 per night (USD)VRBO
Elegant Boutique Room w/ Private Patio & Garden - Duval Street steps away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This listing is for a room within a hotel. ✦ Your room is 270 sq. ft, equipped with complimentary toiletries, TV. ✦ Cl ...
From $445 per night (USD)VRBO
From $2454 per night (USD)VRBO
The Rigby House - Pool, One block from Duval St
- Bedrooms:
- 6
- 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. ...
From $2454 per night (USD)VRBO
From $322 per night (USD)Expedia
Beacon Terrace at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
"Beacon Terrace" in the Truman Annex is a beautifully renovated town home in the historic Foundry in the Truman Annex. ...
From $322 per night (USD)Expedia
From $561 per night (USD)VRBO
A Beachy View at the Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $561 per night (USD)VRBO
From $490 per night (USD)Expedia
**SOUTHERN STAR @ THE MEADOWS** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $490 per night (USD)Expedia
From $146 per night (USD)VRBO
Quiet Old Town Studio - Gated Enclave, Luxury Bidet Bath & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Looking for a peaceful, light-filled sanctuary for a monthly stay in Old Town Key West? This charming private studio off ...
From $146 per night (USD)VRBO
From $1147 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 $1147 per night (USD)Expedia
From $820 per night (USD)VRBO
Atlantis House Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to your private Key West retreat featuring two beautifully appointed suites surrounded by a lush tropi ...
From $820 per night (USD)VRBO
From $739 per night (USD)Expedia
Coco's Poolside Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coco’s Poolside Retreat is a cheerful three-story townhome tucked inside a private, gated mini-compound in Old Town Key ...
From $739 per night (USD)Expedia
From $1339 per night (USD)VRBO
The Flower Power House - Boho Beautiful
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
When you enter the gate next to the painted 1306 sign, you’ll find yourself immersed in this one-of-a-kind tropical wond ...
From $1339 per night (USD)VRBO
From $296 per night (USD)VRBO
VIRGINIA VISTA - Steps from Duval, 2B/R, 2 Bath Retreat with Pool & Large Porch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a few houses off Duval on Virginia Street, VIRGINIA VISTA occupies the upper level of an almost 100-year-old home i ...
From $296 per night (USD)VRBO
From $442 per night (USD)VRBO
VIRGINIA VERANDA, Stylish Old Town 2 B/R, 2Bath, with Pool, Steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Just a few houses off Duval, this wonderful 2 Bedroom, 2 Bath retreat occupies the ground level of an almost 100-year-ol ...
From $442 per night (USD)VRBO
From $499 per night (USD)Expedia
Duval Hideaway | Dog-Friendly w/ Shared Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location Duval Hideaway is the perfect home base ...
From $499 per night (USD)Expedia
From $1974 per night (USD)VRBO
Meadows Manor | Elegant Oasis with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Meadows Manor | Elegant Oasis with Private Pool & Parking --- 3-Night Minimum Stay Required --- Discover the perfect b ...
From $1974 per night (USD)VRBO
From $988 per night (USD)Expedia
Salt Pond Hideaway | Comfortable Condo with Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Salt Pond Hideaway | Comfortable Condo with Pool, Hot Tub, and Close to Beach! Salt Pond Hideaway is your ideal retreat ...
From $988 per night (USD)Expedia
From $941 per night (USD)VRBO
Southernmost Retreat | On Duval! With Hot Tub, Patio
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking Southernmost Retreat is the perfec ...
From $941 per night (USD)VRBO
From $478 per night (USD)Expedia
Kingfish Keep | Lively Escape on Duval! Balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Kingfish Keep | Lively Escape on Duval! Balcony! Kingfish Keep is the perfect escape in the heart of the historic distr ...
From $478 per night (USD)Expedia
From $402 per night (USD)VRBO
Yellowfin Ledge | Ideal Getaway On Duval! Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Yellowfin Ledge | Inviting Getaway On Duval! Balcony! Yellowfin Ledge is the ideal choice for your Key West adventure! ...
From $402 per night (USD)VRBO
From $371 per night (USD)Expedia
Wahoo Way | Charming Hideaway On Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wahoo Way | Charming Hideaway On Duval Street! Escape to Wahoo Way for an unforgettable couple's retreat in Key West! T ...
From $371 per night (USD)Expedia