Resort holiday rentals in Islamorada

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 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.

2 Resort-Style Room w/ Junior Room in Coconut Wing

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.

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.

Ultimate Getaway! Private Beach Access, Pools

Settle into the laid-back rhythm of Key Largo in our 2 Queen Hammock View Unit, offering two queen beds and all the essentials for a comfortable stay. With a small refrigerator, daily housekeeping, and everything you need already provided, you can focus on enjoying the best of our bayside property—from paddleboarding and snorkeling to relaxing under the palms.

Studio w/King Bed, Kitchenette, Pool & Parking

Escape to laid-back island living at La Siesta Resort & Villas in Islamorada. Set on a private beachfront with tropical studios, 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.

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.

2 Bedroom Suite w/Kitchenette, Pool & 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.

2 Suites w/Kitchenette, Pool & 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.

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.

Relax & Recharge! w/Outdoor Pool near the beach

Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. Hurricane Monument & Indian Key Historic State Park are a few miles away.