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.

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.

2 Queen beds Studio w/Pool & Free 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.

Oceanfront Studio King w/Kitchenette & Pool

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.

Oceanfront Studio w/kitchenette & Pool

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.

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.

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 Suites w/Queen Beds, Kitchenette, Pool & 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.

1 Bedroom Suite w/2 Queen Beds, Kitchenette & Pool

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.