Resort holiday rentals in Monroe County

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.

2BR Villa Hyatt Windward Pointe

2BR, 2Ba Villa (1065 sq ft) with full kitchen at 4-star Hyatt Windward Pointe Resort. Infinity-edge pool, outdoor grills, on-site restaurant and amenities. 1 BR has King bed, 2nd BR has queen bed. Each BR has attached full bathroom. Villa includes dining room, living room and furnished balcony with partial ocean view. Quiet location, 1.5 miles to popular Smathers beach, 5 miles to Mallory Square (with attractions, excursions, and nightlife).

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.

HVC The Beach House- your home away from home!

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 $60 is due on checkout.

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.

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.

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.