Key West Vacation Rentals

Find Vacation Rentals in Key West

No Smoking, No Bachelor or Bachelorette parties, and everyone must be over 25 years old unless accompanied by a parent

This property's policy is to refuse certain bookings for the purpose of group events or parties, including pre-wedding stag/bachelor and hen/bachelorette parties

Key West Bahama House

GRAND BAHAMA

$300-$900 Per Night

King Beds: 1 Queen Beds: 2 Baths: 2 Sleeps: 8

The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island Charm have been preserved while bringing you the latest in comfort and convenience. Be prepared to come to know the true meaning of Island Time! For the Grand Bahama all guests must be 25+.
Check Availability

PARADISE ISLAND

$260-$800 Per Night

Queen Beds: 3 Baths: 1 Sleeps: 6

The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island Charm have been preserved while bringing you the latest in comfort and convenience. Be prepared to come to know the true meaning of Island Time! For the Grand Bahama all guests must be 25+.
Check Availability

BIMINI

$350-$950 Per Night

King Beds: 1 Queen Beds: 2 Baths: 3 Sleeps: 6

The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island Charm have been preserved while bringing you the latest in comfort and convenience. Be prepared to come to know the true meaning of Island Time! For the Grand Bahama all guests must be 25+.
Check Availability

NASSAU

$275-$850 Per Night

King Beds: 2 Sleeper Sofa: 1 Baths: 2 Sleeps: 6

The Bahama House is located in Historic Old Town and was built Cirra 1862. An abundance of Dade County Pine and Island Charm have been preserved while bringing you the latest in comfort and convenience. Be prepared to come to know the true meaning of Island Time! For the Grand Bahama all guests must be 25+.
Check Availability
Daily Rentals (3-5 Night Minimum Stay Required)

Sunrise Suites Resort

$225/ Per Night

Bedrooms: 2 Baths: 2 Sleeps: 6

Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling, parasailing, or just soaking up the sun on the warm sand.
Check Availability

BMW Fantasy

$300 - $400/ Per Night

Bedrooms: 2 Baths: 2.5 Sleeps: 6

Roomy Condo located right off Duval Street in Duval Square. Fully Equipped rental, with A/C, complimentary Wi-Fi, and shared heated pool.
Check Availability
Weekly Rentals

Shipyard 197

$1,500 - $2,450/ Per Week

Bedrooms: 2 Baths: 1 Sleeps: 4

Paradise is definitely found in this Non-Smoking, first floor end unit condo only two short blocks off of "happening" Duval Street in Old Town Key West. Located in the upscale, gated community of Truman Annex.
Check Availability

Shipyard 276

$2,100 - $3,850 weekly / Per Week

Bedrooms: 2 Baths: 2 Sleeps: 4

Shipyard 2 bedroom 2 bathroom 7 night minimum rental. This condo has everything you want and more. Paradise is definitely found in this Non-Smoking, first floor end unit condo only two short blocks off of "happening" Duval Street in Old Town Key West. Located in the upscale, gated community of Truman Annex and comes with one assigned parking space.
Check Availability
Monthly Rentals (28 Night Minimum Stay Required)

Coral Hammock #34

$4500 - $6500 Per Month

Bedrooms: 3 Baths: 3 Sleeps: 6

Located in a luxury gated community, this home is located just minutes from Key West, and a 18 hole golf course. Fully Equipped rental, with A/C, complimentary Wi-Fi, private balconies and shared heated pool.
Check Availability

Waters Edge at Key Haven

$5,000 - $9,500/ Per Month

Bedrooms: 4 Baths: 3.5 Sleeps: 8

Fabulous Location In Key Haven With Gulf Views In Front And A Great Boating Canal In 28 night minimum stay requirement! This Spacious 2-story Home Features 4 Bedrooms, 3.5 Baths And Front And Back Porches Boasting Picturesque Gulf And Canal Views.
Check Availability

The Pearl in Paradise

$4,000 - $5,500 / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 4

Located on a quiet street in Key West, a tranquil residential neighborhood close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet.
Check Availability

Banyan Court 204

$6,000 - $7,500 / Per Month

Bedrooms: 2 Baths: 2.5 Sleeps: 4

Park your car and walk everywhere! Sunset celebration is only steps away. The amenities include one assigned parking space, shared, pool and jacuzzi. One pet considered under 25 lbs.
Check Availability

Banyan Court 214

$6,000 - $7,500 / Per Month

Bedrooms: 2 Baths: 2.5 Sleeps: 4

Park your car and walk everywhere! Sunset celebration is only steps away. The amenities include one assigned parking space, shared, pool and jacuzzi. One pet considered under 25 lbs.
Check Availability

Banyan Court 230

$5,000 - $6,500 / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 4

Park your car and walk everywhere! Sunset celebration is only steps away. The amenities include one assigned parking space, shared, pool and jacuzzi. One pet considered under 25 lbs.
Check Availability

Banyan Court 232

$5,000 - $6,500 / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 4

Park your car and walk everywhere! Sunset celebration is only steps away. The amenities include one assigned parking space, shared, pool and jacuzzi. One pet considered under 25 lbs.
Check Availability

Banyan Court 238

$5,000 - $6,500 / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 4

Park your car and walk everywhere! Sunset celebration is only steps away. The amenities include one assigned parking space, shared, pool and jacuzzi. One pet considered under 25 lbs.
Check Availability

The Palms

$5,000 - $7,500 / Per Month

Bedrooms: 3 Baths: 2 Sleeps: 8

Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. Private Pool and Outdoor deck area.
Check Availability

Key Haven Retreat

$5,000 - $7,500 / Per Month

Bedrooms: 4 Baths: 3 Sleeps: 10

This Key Haven open-water home has it all!! Enjoy the custom in-ground pool. Bar-b-que and dine in your waterside gazebo. Great for a Corporate Retreat or Family Getaway, located 5 minutes from Key West.
Check Availability

Boaters Dream

$3,200 - $5,000 / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 6

Private and quiet, this luxurious unit is an ideal place for relaxing away from the noise and partygoers of Duval Street, while still being only a few minutes away from the unique charm of Old Town Key West. Private garage parking is located downstairs, along with elevator access and a security accessed front gate.
Check Availability

Paradise on Eaton

$4,500 - $8,000 / Per Month

Bedrooms: 3 Baths: 3 Sleeps: 6

28 night minimum stay requirement. 3 Bedroom 3 bathroom with a pool located in downtown near the seaport. This home offers you a two bedroom two bathroom in main house with a separate one bedroom cottage with a full bathroom.
Check Availability

Boaters dream on Bahama Drive

$3,500 - $7,500 / Per Month

Bedrooms: 3 Baths: 2 Sleeps: 6

This 3 bedroom 2 bathroom offers a great retreat for boating and relaxing in Key West. Open floor plan living room, kitchen, and dining area. Front patio outdoor covered living space as well as a concrete backyard with a pool. There is seawall for one boat.
Check Availability

Downtown Conch House

$7,000 - $15,000 monthly / Per Month

Bedrooms: 3 Baths: 3 Sleeps: 6

This historic Three bedrooms, three bathrooms, a delightfully open living area and a cozy kitchen that opens onto the outdoor entertainment area. A Key West appropriate pool punctuates the Ipe decking and is surrounded by lush landscaping.
Check Availability

Eliza Street Retreat

$7,000 - $15,000 monthly / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 6

This private conch home has a master bedroom en suite with a king bed and heat producing electric fireplace along with a guest bedroom with a queen bed and Roku TV. There's an additional full bathroom conveniently located just off the living area. Additional sleeping in the loft is accessible by a 'ladder type stairs' not suited for children under 12 year old.
Check Availability

Casa Angelina's Retreat

$15,000 - $20,000 monthly / Per Month

Bedrooms: 4 Baths: 4 Sleeps: 8

Welcome to this lovely 4 Bedroom 4 Bathroom retreat on the water in Key West! Bring up to 2 boats with plenty of dock space and enjoy the amazing waters around Key West. Being right on Riviera Canal you have quick access to the Gulf or the Atlantic! This home is equipped with a fish cleaning station, large in ground swimming pool, home surround sound entertainment system and more! Come enjoy this open floor plan home with a large Kitchen and living area to enjoy with your family or friends! French doors out to the backyard to complete this outstanding home with two of the bedrooms being master suites with ensuite bathrooms, this beautiful retreat surely won't disappoint!
Check Availability

Sunset Marina Getaway

$6,000 - $12,000 monthly / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 4

2 bedroom 2 bathroom luxurious waterfront condominium located at Sunset Marina Waterfront Residences. Sunset Marina is an exclusive gated community with a state of the art concrete floating dock system and has a 6' controlled depth. The Gulf is located right outside the property with immediate access to the Atlantic. Take in Key West World Famous Sunsets from your spacious marina-front balcony, living room and master bedroom with private lanai. This first floor, end-unit condo is the largest 2/2 floor plan available and features more windows and natural lighting than others.
Check Availability

Sea-renity at Sunset Marina

$5,500-$15,000 monthly / Per Month

Bedrooms: 2 Baths: 2 Sleeps: 4

2 bedroom 2 bathroom luxurious waterfront condominium located at Sunset Marina Waterfront Residences. Sunset Marina is an exclusive gated community with a state of the art concrete floating dock system and has a 6' controlled depth. The Gulf is located right outside the property with immediate access to the Atlantic. Take in Key West World Famous Sunsets from your spacious marina-front balcony, living room and master bedroom with private lanai. This first floor, end-unit condo is the largest 2/2 floor plan available and features more windows and natural lighting than others.
Check Availability
Pelican Landing Retreats

ABACO

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

ANTIGUA

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

ANDROS

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 6

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

ARUBA

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

BONAIRE

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

BERMUDA

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

CURACAO

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

DOMINICA

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

ELEUTHERA

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

FLAMINGO

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

FLORIDA

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 8

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability

HARBOUR ISLAND

$500 - $1,000/NIGHT

Bedrooms: 2 Baths: 2 Sleeps: 6

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance.
Check Availability
Pelican Landing Penthouses

ST. CROIX

$850 - $1,800/NIGHT

King Beds: 2 Queen Beds: 2 Baths: 4 Sleeps: 12

St. Croix Penthouse (for 12 people) features four bedrooms and four private baths. The master bedroom has a king bed, one guest bedroom has a king bed, the other two guest bedrooms have two queen beds each for a total of 4 queen beds. There is a living room and dining area. This unit has a fully equipped kitchen including microwave, blender, dishwasher, washer/dryer, and breakfast bar. Living room and one bedroom has sliding glass doors which open onto a private balcony overlooking the water.
Check Availability

ST. JOHN

$850 - $1,800/NIGHT

King Beds: 2 Queen Beds: 4 Baths: 4 Sleeps: 12

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance. The marina offers 16 boat slips accommodating vessels up to 45 feet with a 13-foot beam. Clean your catch at the dock’s fish cleaning station available to all our guests. Then take a few steps to the open-air poolside grill and learn the meaning of fresh fish. Pelican Landing is a short walk to a marina where world-class fishing and scuba charters can be engaged. Check Availability

ST. KITTS

$850 - $1,800/NIGHT

King Beds: 2 Queen Beds: 4 Baths: 4 Sleeps: 12

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance. The marina offers 16 boat slips accommodating vessels up to 45 feet with a 13-foot beam. Clean your catch at the dock’s fish cleaning station available to all our guests. Then take a few steps to the open-air poolside grill and learn the meaning of fresh fish.
Check Availability

ST. THOMAS

$850 - $1,800/NIGHT

King Beds: 1 Queen Beds: 5 Baths: 4 Sleeps: 12

Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or a penthouse for up to twelve guests you will enjoy your stay at Pelican Landing. If traveling with a boat, the facility is boat accessible by powerboat only, because a fixed bridge offers only an 18-foot clearance. The marina offers 16 boat slips accommodating vessels up to 45 feet with a 13-foot beam. Clean your catch at the dock’s fish cleaning station available to all our guests. Then take a few steps to the open-air poolside grill and learn the meaning of fresh fish.
Check Availability