Islamorada Vacation Rentals
Book Islamorada vacation rentals with private pools, ocean views, boat docks, outdoor spaces, and easy access to fishing, beaches, and dining.
About our Islamorada Vacation Rentals
Our Islamorada vacation rentals offer a relaxed way to experience one of the Florida Keys’ most beautiful coastal destinations. Known for world-class fishing, clear blue water, coral reefs, ocean views, and laid-back island charm, Islamorada is perfect for family vacations, couples’ escapes, boating trips, and longer Keys getaways.
Set between Key Largo and Marathon, Islamorada places guests close to beaches, waterfront dining, fishing charters, snorkeling, kayaking, and local attractions such as Theatre of the Sea and Lignumvitae Key Botanical State Park. Spend your days out on the water, exploring the islands, relaxing by the pool, or enjoying sunset drinks with views of the coast.
Choose from Islamorada vacation rentals with private pools, pool access, outdoor spaces, pet-friendly options, accessible layouts, and easy access to beaches, dining, boating, and attractions. Whether you’re planning a peaceful island retreat or an activity-filled Florida Keys vacation, these homes offer a comfortable base for enjoying Islamorada at your own pace.
Popular Islamorada Vacation Rentals
Islamorada is about 90 minutes south of Miami, on Florida’s eastern coast.
The Islamorada Hump is a sea mound that rises almost 200-feet off the ocean floor. It is located about 15 miles off of the Islamorada coast.
West Indian Manatees are residents in the Florida Keys, the region within which Islamorada is located. These beautiful and shy creatures are wonderful to observe in the wild but are not always easy to find. Luckily, there are few places in Islamorada known for manatee sightings, including Robbie’s Marina and dockside restaurants and bars. You can also go on an organized tour or kayak expedition.
Getting to and around Islamorada
Airports
The nearest major airport to Islamorada is the Miami International Airport (MIA), located approximately 80 miles away. This airport is well-connected with domestic and international flights, providing convenient access to the area.
Shuttles and Taxis
Upon arriving at Miami International Airport, you'll find various shuttle services and taxis available to transport you to Islamorada. Shuttles offer shared or private transportation, while taxis provide a direct and efficient ride to your destination.
Car Rental
Renting a car is a popular choice for visitors who want the flexibility to explore Islamorada and its surrounding attractions at their own pace. Multiple car rental companies have facilities at the airport, making it convenient to choose a suitable vehicle for your needs.
Driving
Navigating around Islamorada is relatively easy, with well-maintained roads and clear signage. The Florida Keys Overseas Highway (U.S. Highway 1) connects Islamorada to the rest of the Keys, offering scenic views along the route.
Whether you choose to take a shuttle, taxi, or rent a car, getting to and around Islamorada is hassle-free, allowing you to fully enjoy the breathtaking beauty and activities this tropical destination has to offer.
Discover the Florida Keys beachesSoak up the stunning Key West's Smathers, Islamorada and Bahia Honda State Park beaches. Go sunbathing, swimming, and snorkeling, and discover hidden coves and vibrant coral reefs.
Take a trip to Robbie's MarinaFeed the resident tarpon at Robbie's Marina, an iconic Florida Keys attraction. You can also rent kayaks, go on a snorkeling tour, or dine at waterfront restaurants.
Go SportfishingExperience world-class sportfishing in the "Sportfishing Capital of the World." Charter a boat and head out to catch tarpon, mahi-mahi, marlin, and other prized fish.
Snorkeling & DivingExplore the vibrant underwater world of the Florida Keys by snorkeling or diving. Encounter colorful coral reefs, shipwrecks, and diverse marine life in the crystal-clear waters.
Visit Theater of the SeaVisit Theater of the Sea, a marine mammal park where you can swim with dolphins, sea lions, and even sharks. It's a fun and educational experience for all ages.
Explore the Art GalleriesExplore the local art scene in Islamorada by visiting the numerous art galleries and studios. You'll find a diverse range of artistic styles and creations.
Go Paddleboarding & KayakingTake in the mangrove-lined channels and scenic waterways of Islamorada, by paddleboarding or kayaking. Rentals and guided tours are available - for hassle-free exploration.
Savor the Tiki Bars & SeafoodEnjoy the laid-back island vibe at tiki bars and seafood restaurants. Try fresh catches like conch fritters, stone crab, and key lime pie while sipping tropical cocktails.
Islamorada vacation rentals with Concierge services
Enhance your stay in our Islamorada vacation rentals with Top Villas’ signature Concierge Services, designed to bring effortless luxury to every moment of your trip. Some of our most popular services include villa staff, car rentals, grocery hampers, private chefs and in-villa spa treatments.
What sets our Concierge apart is the personal touch. From the moment you book until the day you depart, our team works closely with you to create a fully-customized, seamless experience.
Oceanfront beach house rentals in Islamorada
Our Islamorada beach house rentals are perfect for relaxed Florida Keys escapes, with ocean views, beach access, and easy island living close to fishing, snorkeling, dining, and local attractions. Set across one of the Keys’ most loved destinations, these homes make it easy to enjoy sun, sea, and laid-back coastal charm.
Spend your days by the shoreline, exploring coral reefs, booking fishing charters, paddleboarding, or relaxing beside the pool after time on the water. Many Islamorada beach house rentals feature stylish interiors, outdoor spaces, beach access, pool access, and room for families, couples, and groups to unwind in comfort.
For guests who want even more from their stay, selected Islamorada resort-style rentals offer access to amenities such as ocean-view pools, marina facilities, fitness spaces, pickleball courts, paddleboards, spa services, and waterfront bars. With the privacy of a vacation rental and the ease of resort-style facilities, these homes offer a memorable way to experience the Florida Keys.
Explore oceanfront beach house rentals in Islamorada
Pet-friendly vacation rentals in Islamorada
Our pet-friendly vacation rentals in Islamorada make it easy to enjoy a Florida Keys escape with your dog by your side. Set close to the water, beaches, parks, dining, and local attractions, these homes offer a relaxed base for guests who want to bring the whole family along.
Choose from stylish Islamorada vacation rentals with ocean views, private outdoor spaces, spacious interiors, and access to resort-style amenities. With room to unwind after days spent exploring, these homes make pet-friendly stays feel comfortable, easy, and memorable.
Beyond your rental, Islamorada offers plenty of ways to enjoy the outdoors with your four-legged friend, from scenic walks and dog-friendly restaurants to parks, boat tours, kayaking, paddleboarding, and nearby coastal spots. Whether you’re planning a family trip or a longer Keys getaway, pet-friendly vacation rentals in Islamorada let you enjoy island life without leaving your dog behind.
Islamorada vacation rentals with pool
Our Islamorada vacation rentals with pools are perfect for relaxed Florida Keys stays, giving guests a refreshing place to swim, unwind, and enjoy the sunshine after days on the water. From resort-style pool access to larger homes with private pools, these rentals offer comfort, flexibility, and easy island living.
Selected Islamorada rentals include access to resort amenities such as ocean-view pools, hot tubs, a beach area, tiki bar, fitness center, and marina, placing everything you need for a carefree coastal escape close by. Spend your days swimming, paddleboarding, fishing, boating, or relaxing by the water before returning to your rental for a peaceful evening.
For guests who want more privacy, larger Islamorada vacation homes may feature private pools, outdoor dining areas, spacious terraces, and personal boat docks. Whether you’re planning a family vacation, couples’ escape, or group getaway, these rentals make it easy to enjoy pool days, ocean views, and the laid-back beauty of the Florida Keys.
Explore Islamorada vacation rentals with pool access
