Resort vacation rentals in Islamorada

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Top-rated resort rentals in Islamorada

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A sailboat glides across calm waters during sunset, silhouetted against a vibrant sky filled with colorful clouds. The sun sets on the horizon, casting warm hues of orange and yellow, while additional boats are faintly visible in the distance.
Hotel room in Key Largo
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.)

Superhost
A two-story townhouse is surrounded by lush palm trees and tropical plants. The facade features a welcoming porch with white railings and bright accents. A parked car is visible in the gravel driveway, set against a clear blue sky.
Resort in Key Largo
4.83 out of 5 average rating, 82 reviews

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.

The image displays an aerial view of a resort featuring a winding pool surrounded by palm trees. A sandy beachfront leads to a calm waterway with docks. The sunlight reflects off the water, enhancing the serene tropical atmosphere.
Hotel room in Islamorada

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.

A spacious living area is highlighted by a large brown leather sectional sofa and a wooden dining table. Natural light streams in through large sliding glass doors, which lead to a balcony. Decorative wall art and a flat-screen TV enhance the inviting atmosphere.
Resort in Layton
4.55 out of 5 average rating, 76 reviews

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.

An outdoor swimming pool is surrounded by lounge chairs, with colorful umbrellas providing shade. Lush palm trees and vibrant tropical flowers frame the area, with a sunset sky reflecting warm hues over the water. Soft lighting enhances the inviting atmosphere.
Resort in Key Largo

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!

A junior suite features a spacious king bed with a decorative throw pillow, complemented by a modern desk. Floor-to-ceiling windows provide natural light and a view of greenery, with access to an outdoor terrace. A wardrobe and chair complete the inviting setting.
Resort in Key Largo
4.83 out of 5 average rating, 12 reviews

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!

A spacious bedroom features a King bed with a patterned throw pillow, complemented by a sleek bedside table and a contemporary mirror. Large windows frame a view of greenery, while a modern workstation is positioned beside the bed, enhancing the room's functionality.
Resort in Key Largo
4.82 out of 5 average rating, 11 reviews

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!

The entrance to the resort is framed by lush greenery and towering trees, with a smooth pathway leading to a light-colored facade. Large windows are visible, allowing natural light to enhance the welcoming atmosphere.
Resort in Key Largo
4.82 out of 5 average rating, 51 reviews

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!

A serene beach scene captures the tranquil turquoise waters meeting a sandy shore, lined with white lounge chairs. Palm trees are dispersed along the coastline, and a wooden pier extends into the horizon under a cloud-dotted blue sky.
Resort in Key Largo
4.84 out of 5 average rating, 98 reviews

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!

An inviting outdoor shared pool area is surrounded by palm trees and lush tropical foliage. Colorful umbrellas shade lounge chairs arranged along the pool's edge. Soft lighting and lanterns create a welcoming ambiance as the sun sets in the background.
Resort in Key Largo

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!

Popular amenities for Islamorada resort rentals

Quick stats about resort rentals in Islamorada

  • Total vacation rentals

    Explore 20 vacation rentals in Islamorada

  • Nightly prices starting at

    Islamorada vacation rentals start at R6,626 ZAR per night before taxes and fees

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Islamorada vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Islamorada rentals

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