Hotel holiday rentals in Windley Key

Hotel room in Marathon

Perched on over a mile of white sand beach

The Oceanfront Balcony Double Queen room at Isla Bella Beach Resort & Spa offers a stunning blend of comfort and breathtaking views. Featuring two plush queen beds, this spacious room is perfect for families or friends traveling together. Step onto your private balcony to enjoy panoramic oceanfront vistas and the soothing sounds of the sea. The room is elegantly appointed with coastal-inspired décor, a modern bathroom, complimentary WiFi, a flat-screen TV, mini refrigerator, and coffee maker.

4.7 out of 5 average rating, 33 reviews

Anchorage Resort and Yacht Club

Explore the Florida Keys from our waterfront slice of paradise. Our spacious 1-bedroom suites accommodate 4, include a full kitchen, and have a beautiful waterfront. Kick back and relax on our charming grounds and enjoy our pool, fish from our docks, enjoy some time under our tiki huts, or moor your boat with us. Weʻre just minutes away from John Pennekamp Coral Reef State Park and dozens of other must-do Key Largo attractions. Ditch the hotel room and book our large rentals for your stay!

5 out of 5 average rating, 5 reviews

Double Room with - Ocean View

Welcome to Snappers Hotel Rooms Nestled on Mile Marker 94.5 in Key Largo, Snappers offers more than just a place to stay — it’s a local legend perched on 3 acres of waterfront bliss. Whether you're here to unwind for the weekend or extend your stay in the Florida Keys, our cozy rooms put you steps away from the ocean, live music, fresh seafood, and the locals-only Turtle Club tiki bar. Wake up to sea breezes and experience the charm that has made Snappers a Keys favorite since 1984.

4.67 out of 5 average rating, 6 reviews

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.)

5 out of 5 average rating, 32 reviews

Hotel room in Duck Key

Conch Key Villas #1. Fun, fishing & great sunsets

Studio One's waterfront rental is located on the ground level. Our units differ vastly from other Florida Keys lodgings because our property is right on Florida Bay. If you trailer your boat, the dockage is a few feet from the back door. Our docks can handle boats up to 25’ and you can park your trailer in our front lot. There is a boat ramp just two blocks away. Studio 1 can sleep 2 adults and one child (up to 12 years). We have a king size bed and a futon.

4.96 out of 5 average rating, 53 reviews

Hotel room in Conch Key

1-bedroom suite - Full Kitchen, Dockage, Boat Ramp

Sunset Villas is a small lodge located on the quaint island of Conch Key (MM 63, between Marathon & Islamorada). This listing is for our 1-bedroom, OPEN WATERFRONT suite with full kitchen. Includes one assigned parking space, boat trailer parking, use of our on-site Boat Ramp, Dockage for a boat 25' or less, use of two bikes & use of our two person kayak. Registered guests only. Sunset Villas On Conch Key - A Place for the Chosen View!

4.75 out of 5 average rating, 64 reviews

Motel Room in Key Largo

Welcome to your perfect Florida Keys getaway! This delightful, coastal-themed 1-bedroom, 1-bathroom motel room is your temporary escape pod, nestled within the Sun Outdoors Key Largo RV Resort. We're perfectly situated for exploring the best of the Keys, with our own stunning private beach as well as local beaches (where your biggest decision is 'flip-flops or bare feet?', stunning reefs (hello, Nemo!), and fantastic restaurants.

Hotel room in Tavernier

New place to stay

Key Largo 1BR w/ Partial Ocean View, Pool & Beach

Relax and rejuvenate in our tropical paradise-inspired 1B/1B condo. Enjoy a fully equipped kitchen, washer/dryer, and cozy living area for a convenient vacation. Nestled in a 60-acre sanctuary, it's a tranquil oasis away from city life. Close to Key Largo and Islamorada attractions, you'll have easy access to snorkeling, diving, fishing, birding, and dining. Plus, take advantage of our private sandy beach and marina.

Hotel room in Islamorada

4.75 out of 5 average rating, 4 reviews

Hit the pool or take kayaks out on the ocean

Bi-level suite featuring a upstairs bedroom with one king bed. On the main level, there is a small dining area and living area including a queen-size sofa bed, microwave, mini fridge, coffee maker and cutlery. Photos shown depict a typical guest room, while each of our rooms is unique and may vary slightly from what is shown while providing all the same amenities. Room may have a view of the pool or the courtyard.

4.84 out of 5 average rating, 259 reviews

Hotel room in Marathon

Wreckers House King Room - Adults Only

Adults-only building for guests ages 21+ only. Thoughtfully furnished with mixed metals and woods, the Wreckers House tells the story of ships and their crews of "wreckers" who once salvaged goods from the sunken ships in the Florida Keys. Enjoy a sunrise view and an ocean breeze from your private balcony that overlooks the pool and the Atlantic. This room has a mini fridge and an espresso machine.

4.82 out of 5 average rating, 76 reviews

Resort in Key Largo

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.