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.

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*

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.)

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 Genuine Key Largo Experience! Beach Access, Pool

Find space to relax and recharge in our Junior Suite in Coconut Wing, featuring a private bedroom with a king bed and a separate living area with a sofa bed. Whether you're returning from a day of kayaking, snorkeling, or beachside lounging, this suite offers the comfort and convenience you need—with a small refrigerator, daily housekeeping, and all essentials provided. It’s a welcoming retreat in the heart of our lively bayside property.

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. 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.

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.

The Galleon, Key West

Overlooks the bay and boat slips. Unit is on 4th floor. Two blocks from Duval Street and Mallory Square. Three blocks from Truman Annex. Great view from balcony of boat docks and the Coast Guard base across the bay. Don't really need a car if flying in. This is the place to be if visiting for the first time or visiting again.