Resort vacation 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.)

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.

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.

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.

Stay in Style! Beach Access, Outdoor Pool!

Whether you’re looking for a romantic getaway or a place to escape for a couple of days, our property has everything you need to make your stay unforgettable!

Explore Key Largo! Beach Access, Pool, Parking!

Whether you’re looking for a romantic getaway or a place to escape for a couple of days, our property has everything you need to make your stay unforgettable!

Pool, Private Beach Access, Pet-friendly!

Whether you’re looking for a romantic getaway or a place to escape for a couple of days, our property has everything you need to make your stay unforgettable!

Keys Escape! Close to Beach Road, Onsite Pool!

Whether you’re looking for a romantic getaway or a place to escape for a couple of days, our property has everything you need to make your stay unforgettable!

Ultimate Getaway! Private Beach Access, Pools

Whether you’re looking for a romantic getaway or a place to escape for a couple of days, our property has everything you need to make your stay unforgettable!

Key Largo Escape! Outdoor Pool, Beach Access!

Whether you’re looking for a romantic getaway or a place to escape for a couple of days, our property has everything you need to make your stay unforgettable!