Skip to content

Key West Vacation Rentals in the Florida Keys

Book Your Key West, Florida Keys Vacation Rental Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Key West, Florida Keys, Florida.

Galleon Marina & Resort B22 - Key West Condo

The Galleon Marina & Resort Luxury Rental - 2 Bed/2 Bath

The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the United States. Within walking distance to several bars and restaurants, bars, Duval Street, Mallory Square & many other historic site About the Galleon: Overlooking the Gulf of Mexico in historic Old Town, The Galleon Resort puts you in an ideal spot to enjoy the countless charms of Key West. Mingle with friends new and old a.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Vacation Home

Southernmost1xOFBalK - Key West Hotel

Modern Unit! 3 Heated Pools, Private tanning Pier, Free Onsite games

NOTE: The safety and security of our Guests and Team Members have always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the n.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

24North2xPremium2Qs - Key West Hotel

Beach Getaway! 2 Comfy Units, Free High Speed Internet, Gym, Pool

Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help you have a great vacation. Close to kayaking, scuba diving and snorkeling, and many other watersports, head out and seek adventures! When you get back from exploring the great outdoors, rest on the property’s premium bedding, unwind watching your favorite shows on your 42” flat-screen TV, or leisure by surfing the internet .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 Hotel Rentals

Vacation Home

24North2xDeluxe2Qs - Key West Hotel

Beach Getaway, Marina On-Site, 2 Queen Units, Pool!

Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help you have a great vacation. Close to kayaking, scuba diving and snorkeling, and many other watersports, head out and seek adventures! When you get back from exploring the great outdoors, rest on the property’s premium bedding, unwind watching your favorite shows on your 42” flat-screen TV, or leisure by surfing the internet .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 Hotel Rentals

Vacation Home

Southernmost1x1Resi - Key West Hotel

Convenient Family Unit, Free Onsite games, Gym, 3 Heated Pool and Bars

NOTE: The safety and security of our Guests and Team Members have always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. All the comfort of home from an exclusive three-bedroom, three-bath, 2000 square foot executive suit.......read more

3 Bedroom(s)
1 Bath(s) - Sleeps 8 Hotel Rentals

Vacation Home

TheMarker 1xPool&GVK - Key West Hotel

Amazing Vacation for 2 Guests! Pools, Gym, Tiki Bar!

NOTE: The safety and security of our Guests and Team Members has always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktai.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

Colony Poolside - Key west Cottage

Colony Poolside: A charming bungalow near the historic cemetery

Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork. A vaulted ceiling with exposed beams and huge transom windows that extend all the way to the tip of the roof add a bright and airy feeling to the cozy space. The ful.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Cottage Rentals

Vacation Home

24North2x2Qs - Key West Hotel

Fantastic Land and Sea Vacation! 2 Comfy Units, Beach, Pool, Gym

Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help you have a great vacation. Close to kayaking, scuba diving and snorkeling, and many other watersports, head out and seek adventures! When you get back from exploring the great outdoors, rest on the property’s premium bedding, unwind watching your favorite shows on your 42” flat-screen TV, or leisure by surfing the internet .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 Hotel Rentals

Vacation Home

TheMarker 2x1SrntyS1 - Key West Apartment

BEST VACAY! 2 COMFY UNITS, POOL GYM AND BAR

NOTE: The safety and security of our Guests and Team Members has always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktai.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 8 Apartment Rentals

Vacation Home

Palm Island Suite-Top of Duval - Key West Condo

Palm Island Suite at Top Of Duval

Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. Perfectly located between Key West’s famous Duval Street, and a charming residential lane in Old Town, this property offers the best of all worlds. One door leads to lively entertainment, shopping and world famous dining; and the other the door to your own private swimming pool and tropical landscape.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Southernmost1xDluxeK - Key West Hotel

Duval Street where Old Town meets the Atlantic! Modern Unit, 3 Heated Pools

NOTE: The safety and security of our Guests and Team Members have always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the n.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

TheMarker 1x2Q - Key West Hotel

Cozy Vacation Escape for 4! 3 Pools, Gym, Tiki Bar

NOTE: The safety and security of our Guests and Team Members has always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktai.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Hotel Rentals

Vacation Home

Vacation Rentals - Key West House

Rare on the Island of Key West

t's rare on the island of Key West but if you are looking for a beautiful completely renovated home, with privacy, water views, and boating access this is it. Where the Sunrise and Riviera canals meet you will find this gorgeous 3 bedroom/3 bath estate set on a large lushly landscaped lot. In 2005 the home was rebuilt with impact resistant windows and doors, custom kitchen, designer baths, new plumbing, new electric, new roof, step down sea wall,.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 House Rentals

Vacation Home

Southernmost1xOFBalK - Key West Hotel

Duval Street where Old Town meets the Atlantic! Modern Unit, 3 Heated Pools

NOTE: The safety and security of our Guests and Team Members have always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the n.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Hotel Rentals

Vacation Home

Vacation Rentals - Key West Condo

Sunsets over the water

Sunset views over the water has this large 1/1 with 1 assigned parking space. Only a few minutes from the Island of Key West, and many seafood restaurants on the water. Catch fish steps away from your home, ride your bike in the overseas trail, very quiet area at night, minutes from the Boca Chica air base........read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Gates1x1LifestyleKing - Key West Hotel

Key West Escape! Great and Spacious Unit, Pool, Gym, Bar, Restaurant, Parking!

Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes’ walk to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool and pool bar are a relaxing spot to spend an afternoon in the sun. Hourly shuttle services are available to Old Town Key West and free parking is available to all guests throughout their stay.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 3 Hotel Rentals

Vacation Home

Key West Sunset Harbor 2BR - Key West Resort

Old Town Key West Sunset Harbor 2-Bedroom Oasis, + Amenities

Please verify availability prior to booking. Inquire for exclusive rates or Feel free to request a custom rate for your specified dates of travel. 7-Night Stay Required (Sunday-Sunday Check-In/Check-Out ONLY) - short-stay fees may apply for stays less than 7-Nights. We look forward to welcoming you to this waterfront retreat overlooking the Gulf of Mexico. Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Resort Rentals

Vacation Home

Cloud 9 - Nightly Rental - Key West House

~ CLOUD 9 ~ Perfect Home In Heart of Downtown KW w/ Heated Pool & Parking

THE PROPERTY: The Absolute Best Luxury Private Vacation Rental Home by Duval Street In Old Town. Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find yourself in the private brick courtyard facing the home with its French doors and balconies. As soon as you see the beautiful custom pool w.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 7 House Rentals

Vacation Home

Vacation Rentals - Key West House

CoCoMo - Monthly Rental

Located on quite Peacon Lane this one bedroom one bath new renovated cottage is your perfect Key West Hideaway. One block from the historic Key West Harbor there is a wide varieties of seafood restaurants, shopping and attractions for everyone. This is the perfect home for a couple to relax and enjoy the island life. The kitchen offers new appliances and is equipped with everything you would need to cook your catch of the day. There is also a .......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals

Vacation Home

Chavez House - Nightly Rental - Key West House

~CHAVEZ HOUSE~ World Class Luxury Home w/ Heated Pool In Heart of "Old Town"

THE PROPERTY: The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was built in 1870 and is in the National Register of Historic Places. Beautifully renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool and calming color palette. At 1415 sq. ft. this home comfortably sleeps 6. Enjoy a dip in the private pool, work on your tan on the large exterior d.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Vacation Home

Namaste Eco Lodging - Key West Boat

Eco Lodging at 5-Star Resort - Perfect for Couples and Families

Triple Level Cleaning and Disinfection to keep you safe! Stay aboard the air conditioned Reef Dreamer at the Perry Hotel Key West and experience the joy of boat life at the newest resort in the Florida Keys. Watch manatees and tarpon from the back deck while enjoying all the amenities of the new Hotel Perry Key West. The Reef Dreamer is a perfect way for a couple or small family to truly experience the boat life without sacrificing any of the lux.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Boat Rentals

Vacation Home

Southernmost1xPrtOV2 - Key West Hotel

Modern Unit! 3 Heated Pools. Private tanning Pier, Free Onsite games

NOTE: The safety and security of our Guests and Team Members have always been our priority. We are taking additional precautionary measures to ensure our facilities are maintained to the highest standards and to do our part in reducing the spread of coronavirus. Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the n.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Hotel Rentals

Vacation Home

Vacation Rentals - Key West Condo

Spacious 1 bedroom, private heated pool, private yard, deck, covered porch

Spacious 1 bedroom w/additional queen sleeper sofa for short term guests. 1st floor in Old Town. Only 2 other condos in compound. On desirable Frances Street, just 3 blocks from seaport, 6 blocks to Duval. Granite kitchen, Washer/Dryer, outdoor propane grill, tile floors, tiled shower, central AC, large screen T.V., bedroom T.V, WiFi. Fully furnished. Walk out of multiple french doors to your private heated pool, covered porch, deck and private y.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Vacation Home

24North4xDeluxe2Qs - Key West Hotel

Fantastic Land and Sea Vacation! Four Comfy Units, Beach, Pool, Gym

Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help you have a great vacation. Close to kayaking, scuba diving and snorkeling, and many other watersports, head out and seek adventures! When you get back from exploring the great outdoors, rest on the property’s premium bedding, unwind watching your favorite shows on your 42” flat-screen TV, or leisure by surfing the internet .......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 16 Hotel Rentals

Vacation Home

Gates3xStandard2Qs - Key West Hotel

Ultimate Beach Esacape! 3 Great Units Near Attractions, Pool, Gym, Parking, On-site Bar!

These are THREE separate units. Please note: these are not adjoining units, units may not be located next to each other - the exact units are assigned upon arrival, based on availability. Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes’ walk to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool an.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 12 Hotel Rentals

Vacation Home

Gates1xStandard2Qs - Key West Hotel

Best Vacation Awaits! Modern Unit Near Attractions, Pool, On-site Bar and Restaurant, Parking!

Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few minutes’ walk to several local attractions. An onsite restaurant serves Latin-inspired tapas with local ingredients. The refreshing pool and pool bar are a relaxing spot to spend an afternoon in the sun. Hourly shuttle services are available to Old Town Key West and free parking is available to all guests throughout their stay.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Hotel Rentals

Vacation Home

Scroll To Top