Resort vacation 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).

Oceans Edge Key West Resort, Hotel & Marina!

This stylish place to stay is perfect for group trips. This smoke-free hotel features a marina, 6 outdoor pools, and a restaurant. Additionally, a 24-hour fitness center, a bar/lounge, and a poolside bar are onsite. All 175 soundproofed rooms feature minibars and room service. Comforts include Egyptian cotton sheets and down comforters, and guests will also find conveniences like refrigerators and coffee makers.

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 #405 Banyan Resort Key West, FL

With pools, a hot tub, Tiki Bar, BBQ grills, and a 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 unit has a large deck with a commanding view of the property from 3 stories up.

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.

Studio - Hyatt Residence Club Key West

Tropical Key West welcomes you to a classic Florida studio condominium, offering a plush king-size bed, casual living area with TV and DVD player, and kitchenette with microwave and mini-refrigerator. Amenities include: onsite washer and dryer, coffeemaker, ceiling fans and wireless Internet access