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.

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*

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.

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.

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.

Hyatt Windward Pointe Resort: Beachfront Condo

Experience this tropical paradise as you relax in a family friendly timeshare within the Hyatt Residence Club. Have breakfast on the oceanfront balcony followed by a dip in the pool/hot tub or visit the nearby spa. There are 2 bedrooms and 1 sofa bed which can fit 6 people. 2 bathrooms with a spa tub in master bedroom. Fully functioning kitchen and dining area in addition to an in-home washer/dryer unit.

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.

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

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.

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.

Spacious 1BR Suite w/ Kitchenette | 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.