Resort holiday rentals in Key West

Luxury Condo @ Key West Private Beach Resort

Two-Bedroom Villa Sleeps up to 6 guests Free Parking Lush tropical beauty welcomes you to a spacious residential-style condominium featuring a primary bedroom suite with king-size bed and adjoining bath with walk-in shower, and a guest suite with king-size bed and full bath. Lavish amenities include fully equipped kitchen, dining area, living room + sofa bed, screened-in balcony looked at this charming & upscale place to stay. Private beach with food & cocktails served on the pier or pool area.

Don't miss out! 2br penthouse (9/21-9/26)

This is a large, two-bedroom, two-bathroom villa with separate living room, kitchen, and dining room at the exclusive Galleon Resort! This villa offers two balconies overlooking the marina and high ceilings - perfect for relaxing after a long day of enjoying Key West! The Galleon is right on the water, so you can enjoy watching boats at the marina, walk over to Duval for a drink, Mallory Square for the sunset, or Schooner's Wharf to mingle with locals. You also get one parking space.

Enticing two Bedroom at Hyatt Sunset Harbor!

We are able to offer reservations in weekly increments with arrivals and departures on Fridays, Saturdays, and Sundays only. Discover a relaxing oasis overlooking the Gulf of Mexico in the heart of Old Town, steps from the shops, galleries, and cafes of Duval Street, and close to the nightly sunset celebration at Mallory Square. Hyatt Sunset Harbor’s spectacular gulf coast setting is matched only by the gracious service, top-tier amenities and meticulous attention to detail.

A Katie's Cottage

Relax in this private cottage located in the heart of Old Town Key West. The cottage sports 2 private bedrooms with queen beds, 2 bathrooms, a queen pullout couch, full living room and kitchen, & deck area that surrounds one of our pools. The room is accessible by three steps up. Enjoy our daily complimentary breakfast, 3 pools, wifi, and TV. Perfect for a group of up to 6 or families! We have paid parking first come first serve, or you can find free street parking.

Don't miss out! Amazing studio (9/21-9/26)!

Amazing opportunity to stay at the Galleon Resort. This studio villa offers a private entrance to a quiet, interior room on the fifth floor of this resort. You'll have a private bedroom and bathroom with a small kitchenette. You'll be within walking distance of so many amazing Key West favorites - Duval Street, the marina, Old Town, and plenty of dining options. The Galleon offers a private pool, beach, water activities, tiki bar, and waterfront restaurant.

Don't miss out on this 1br (9/21-9/26)

This is a large, one-bedroom villa with separate living room, kitchen, and dining room at the exclusive Galleon Resort! This villa offers two balconies overlooking the marina and high ceilings - perfect for relaxing after a long day of enjoying Key West! The Galleon is right on the water, so you can enjoy watching boats at the marina, walk over to Duval for a drink, Mallory Square for the sunset, or Schooner's Wharf to mingle with locals.

Hyatt Beach House Key West- Nov. availability!

You'll enjoy your time at this cheerful getaway. The property has 3 floors with beautiful views. Suites come fully equipped with a kitchen, 2 BR, 2 BA. King beds in Brs and a double sleeper sofa in living area *PLEASE NOTE- Once you request specific dates, I reach out to Hyatt Vacation Club for availability. We own points, not a specfic unit. * A cleaning of $125 will be collected upon checkout at the property.

Charming 2 Bedroom Suite Beach Resort

Our private tropical paradise, reminiscent of days gone by, sits quietly and serenely on the Atlantic side of Key West. Here you will find a blend of old island architecture, lush vegetation and quiet walkways flowing onto bright white verandahs. Each of our layouts offers its own touch of uniqueness, be it a high-pitched ceiling, a private balcony or a spectacular panoramic view.

1BR #405 Banyan Resort Key West, FL

With pools, a hot tub, Tiki Bar, BBQ grills, and a kitchen in each unit you can enjoy the lush private surroundings and still be close to the heart of Key West, Hemingway Museum, Sloppy Joe's, 1 block off Duval. ONLY dates on calendar are available. This unit has a large deck with a commanding view of the property from 3 stories up.

Banyan Resort

This suite in a tropical, historic resort has all of the comforts of home including a kitchen complete with all of the amenities necessary to make your island escape a relaxing experience. Perfectly located in the heart of Old Town one block from Duval Street. Resort has two pools, a jacuzzi and a tiki bar.

3 BEDROOM 3 BATHROOM ISLAND TOWN HOME

This Island Town Home is conveniently located in Long Key which is in the middle of the Florida Keys right in between Islamorada and Marathon. It is a 2-hours drive from Miami airport and only 90 minutes from Key West. This mid-way location is perfect for exploring all the Florida Keys.

Banyan Resort Treetop

This suite in a tropical, historic resort has a complete kitchen and large private deck. Perfectly located in the heart of Old Town one block from Duval Street. There are two pools, a jacuzzi and a tiki bar.