Resort holiday rentals in Key West

A bright living area is highlighted by natural wood paneling and soft lighting. A spacious blue sofa is paired with a simple coffee table, while a dining table for four is visible. A kitchenette with essential appliances is also included, creating a functional and welcoming space.

5 out of 5 average rating, 4 reviews

Orchid Suite

PET FRIENDLY up to 2 pets!! Unwind in this one bedroom suite located in the heart of Old Town Key West. This sun filled suite features a living room with a queen sleeper sofa, a kitchenette with a microwave\convection oven, a separate bedroom with king sized bed and a gated private outdoor area. Enjoy our complimentary breakfast, 3 pools, complimentary wifi, and smart TVs. Sleeps 4. We have very limited paid parking, first come first serve. *$25/pet per night, paid upon arrival to the property*

The resort features a large outdoor pool surrounded by lush palm trees and comfortable lounge chairs. The multi-story building is partially visible in the background, showcasing multiple balconies and inviting walkways that enhance the tropical atmosphere.

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 spacious living area features a neutral-toned sofa with decorative cushions and a vibrant wall art piece depicting palm trees. Natural light floods the space through glass doors, which provide access to an outdoor area. A round dining table is paired with four orange chairs.

4.93 out of 5 average rating, 14 reviews

Parrot's Perch

The Parrot’s Perch (formerly Zeke’s Retreat) is a sun filled suite with soaring ceilings features a living room with a queen sleeper sofa, a wraparound porch with a hammock, a kitchenette with a convection \microwave oven and a bedroom with a king size bed with private balcony overlooking the palm trees. Sleeps 4 people. Complimentary breakfast included. Enjoy 3 pools, wifi, and smart TVs. Very limited paid parking available onsite on a first come first serve basis.

Guest favourite

A cozy living space is adorned with warm wood paneling and features a comfortable sofa with floral cushions. Two armchairs flank a wooden coffee table, while natural light filters through the windows, illuminating the room. Art depicting vibrant houses hangs on the wall.

4.91 out of 5 average rating, 33 reviews

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.

A bright living area features large sliding doors opening to a stunning ocean view. The space includes a green sofa, two comfortable chairs, and a glass dining table. Light-colored walls enhance the relaxed, airy ambiance, with tropical-themed artwork adding a touch of color.

4.72 out of 5 average rating, 74 reviews

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.

New place to stay

Galleon Resort, Private Beach, Tiki Bar, Pool

Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the Jacuzzi or sauna during your stay or work out in the onsite fitness center. Enjoy fishing off the private dock, or rent bicycles and take in all that Old Town Key West has to offer.

Studio w/King Bed, Kitchenette, Pool & Parking

Escape to laid-back island living at La Siesta Resort & Villas in Islamorada. Set on a private beachfront with tropical studios, enjoy poolside cocktails at Sidecar, kayak and paddleboard rentals, and shared access to sister resorts via water taxi or shuttle. Ideal for families, couples, or groups seeking a serene Keys getaway.

Oceanfront Studio King w/Kitchenette & Pool

Ocean view Studio w/Kitchenette & Pool

4.17 out of 5 average rating, 6 reviews

2 Bedroom Suite w/Kitchenette, Pool & Free Parking

Escape to laid-back island living at La Siesta Resort & Villas in Islamorada. Set on a private beachfront with tropical suites, enjoy poolside cocktails at Sidecar, kayak and paddleboard rentals, and shared access to sister resorts via water taxi or shuttle. Ideal for families, couples, or groups seeking a serene Keys getaway.