Islamorada Vacation Rentals
Islamorada vacation rentals offer a laid-back island experience with a collection of waterfront homes, canal-front retreats, and coastal-style condos designed for comfort and connection. Choose from Islamorada vacation homes featuring multiple bedrooms, full kitchens, private pools, and outdoor living spaces—ideal for families, couples, and group getaways. Many Islamorada rentals include sought-after amenities such as boat docks, water access, and expansive views of the Atlantic Ocean or Florida Bay.
Located in the heart of the Upper Florida Keys, Islamorada blends natural beauty with a relaxed yet refined coastal atmosphere. Known as the “Sportfishing Capital of the World,” this island village is a favorite for boating, fishing, and water-based adventures, while still offering quiet neighborhoods and scenic surroundings. With a mix of oceanfront and bayfront properties, Islamorada vacation rentals provide the perfect balance of activity and relaxation.
Why Stay in Islamorada?
Islamorada offers a unique combination of upscale island charm and easygoing coastal living. Guests can spend their days on the water—whether fishing offshore, exploring the backcountry, or snorkeling in clear, shallow reefs—and their evenings enjoying waterfront dining and unforgettable sunsets.
The central location of Islamorada makes it easy to explore the Upper Keys while still feeling tucked away from the crowds. From peaceful canal-front neighborhoods to luxury waterfront estates, Islamorada rentals offer a range of options for every type of traveler.
Waterfront Living & Boating Access
One of the biggest draws of Islamorada vacation rentals is the connection to the water. Many homes offer private docks, boat lifts, and quick access to both the ocean and the bay, making it easy to bring your boat or book a charter nearby.
Outdoor living is a key part of the experience, with spacious decks, shaded patios, and private pools designed for relaxing after a day on the water. Whether you're watching the sunset from your dock or gathering with family by the pool, Islamorada rentals are built to make the most of island living.
Plan Your Islamorada Getaway
From fishing trips and sandbar days to quiet mornings by the water, Islamorada offers a vacation experience that feels both effortless and memorable. With comfortable homes, scenic surroundings, and direct access to everything that makes the Florida Keys special, Islamorada vacation rentals provide the perfect setting for your next coastal escape.
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13 properties available
Marvelous views will fill your vision when you call this sun-soaked home your next vacation destination! When you can peel yourself away from the tantalizing turquoise views, check out the area's many amusements. All less than eleven miles away, you will discover the Laura Quinn Wild Bird Sanctuary, Theater of the Sea, the History of Diving Mus
Whether you spend your next Florida vacation playing in the cool surf or hanging out with good friends on the private patio, you will love staying in this gorgeous retreat. Guests will be delighted by the fantastic location of this condo, offering a large pool, 2 tennis courts, a furnished clubhouse, first-come-first-served dockage, and a bayfront
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, boasting serene oceanfront views from two private balconies. The top-floor location immerses you in beautiful water views and gentle breezes on your private Tavernier Escape. Enjoy on-site amenities like the community pool and gazebo, a waterfront caf&eac
Book this newly renovated home that sits on a major canal, where guests can tie off a boat, in the Indian Waterways neighborhood. The nautical-themed decoration throughout the house will truly help you leave all of your worries behind and focus on having a great time! The family dog is also welcome to join in the fun here. The home features a 60-fo
Your Waterfront Escape in the Heart of Islamorada Awaits! Welcome to your dream getaway in the Florida Keys—where turquoise waters, tropical breezes, and that unmistakable “island time” feeling set the tone for an unforgettable stay. Nestled right on the water in beautiful Islamorada, this spacious 3-bedroom home offers the perfec
Sun-soaked days and cool ocean breezes await you when you book your next retreat to this oceanfront Key Largo getaway. Featuring sweeping ocean views and shared amenities like a pool, on-site tennis, and beach access, fun will always be easy to find! Steps from the gently rolling waves, and just over seven miles from the heart of the island, you
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA, and we cannot make any exceptions. Enjoy incredible beach and ocean views from this family-friendly, waterfront retreat. This home features a beautiful, sandy backyard that leads directly to the ocean, a private boat dock, four beach cru
Step into your own slice of paradise at this sunlit, open-concept home overlooking the turquoise waters of the Florida Keys. With enchanting views from nearly every room, Tollgate Tides is the perfect retreat for a surf trip with friends, a romantic couples’ getaway, or a family vacation by the shore. ⭐ Location Highlights • Robbie&rsquo
Escape the hustle and bustle of everyday life in the tropical Florida Keys, where tranquility and fun await. This condo is steps away from the water, with all you ever need for entertainment in a 10-mile radius. Tour the area and check out Rain Barrell Village, Theater of the Sea, the History of Diving Museum, or the Laura Quinn Wild Bird Sanctuary
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA, and we cannot make any exceptions. This home is perfect for anyone coming to the Keys to spend time on the water. The two-story home sits on the widest canal in Hammer Point that leads to Florida Bay and has its own private dock capable
You deserve a dreamy beach vacation, and this coastal condo is just the place to kick back and soak up that salty air. Wake up and look out at the greenery and unique landscape with a cup of coffee in hand. Head into the fully equipped kitchen and whip up a hearty breakfast for the group on modern appliances. When it is time to head out for the day
The Tree Lane Fish Camp: Updated, Cozy home in TavernierBed Sizes: 2 Queen, 1 Double Trundle Bed, 2 Double Sleep SofasWelcome to your laid-back diving retreat in Tavernier, where life moves with the tides and every day ends with a sunset over the water. Nestled in the heart of the Florida Keys, this home is built for anglers, boaters, and anyone wh
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