Resort holiday rentals in Monroe County

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.

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.

Key Largo Cottages w/ Free Sailboat, Kayaks + More

The Mermaid is one of the cottages in Key Largo Cottages located on the bay side of Key Largo near some of the best dive/snorkel sites, island excursions, bars, restaurants, & the Everglades. A stay here comes with unlimited use of our kayaks, canoes, paddle boards, snorkel gear, some fishing gear, &, of course, the use of one of our 22' sailboats, if you have recent sailing experience on keel boats! You won't find a better deal in the Keys! (This is NOT a dog friendly cottage.)

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.

Coral Townhome

Built as a townhouse-style apartment with two levels, the Coral Townhome includes one bedroom with a king-size bed and a full bathroom, while the downstairs level offers a private bedroom in the back with a full-size mattress bunk bed, a full kitchen, another bathroom, and a living room equipped with a sofa bed. Featuring two bedrooms, these townhouses accommodate up to five guests.

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.

1BR Condo Banyan Tree, KeyWest Unit 505/701

With pools, a hot tub, Tiki Bar, BBQ grills, and a full 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 1BR Listing covers unit 701 in Oct and 505 in July. Steps up to condo. Steps up to loft.

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.

Azul Del Mar Garden Queen-size

Key Largo may be famous for its intricate coral reef, the eco-wonderful everglades, spectacular sunsets, mouthwatering seafood or even Bogart and Bacall...but only a select few know that nestled in a tropical garden, far from the hustle and bustle is an intimate all-adult Florida Keys boutique hotel called Azul del Mar.

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.