Vacation rentals in Islamorada

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Top-rated vacation rentals in Islamorada

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Superhost
A serene outdoor seating area is presented with two cushioned sofas and a wooden coffee table, overlooking a waterfront. The sunset creates a vibrant orange and yellow backdrop, reflecting off the water. Additional seating in the distance enhances the tranquil atmosphere of the space.
Camper/RV in Key Largo
4.93 out of 5 average rating, 136 reviews

Paradise Casa Bayfront sunsets,pool,King bed ,dock

Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

Guest favorite
Houseboat in Islamorada Tavernier
4.9 out of 5 average rating, 261 reviews

Florida Keys Houseboat, unique waterfront stay-

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

Guest favorite
The charming cottage displays a pastel-colored exterior with a triangular roof and white trim. A small front porch is set above the entrance, flanked by two sets of French doors. Lush greenery and a white picket fence enhance the welcoming entryway.
Townhouse in Duck Key
4.96 out of 5 average rating, 188 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Superhost
A modern studio is showcased, featuring a comfortable queen-sized bed and lounge area equipped with a Smart TV. Natural light floods the space from large windows. The kitchen is outfitted with stainless steel appliances, while the outdoor area includes tiki huts with thatched roofs, ideal for relaxation.
Apartment in Key Largo
4.9 out of 5 average rating, 314 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Top guest favorite
A multi-story home is reflected in the calm water, showcasing a spacious deck with dining furniture under palm trees. Lush greenery surrounds the property, enhancing the serene environment. The structure features a staircase leading to a balcony, offering views of the tranquil setting.
Home in Key Largo
4.9 out of 5 average rating, 137 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

Close to restaurants and dining, parks, and great views. You’ll love my home because of the peaceful atmosphere, sitting on your own dock watching the boats pass by or friendly manatees swim up. Enjoy swimming in the pool or just relaxing on the patio with a drink in your hand. This home is in a private, gated community and about 10 homes from the bay. A Pontoon boat rental is available(ask for details). Great for families, couples and/or adventurers. Must be age 25 or older to book.

Top guest favorite
A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.
Tiny home in Key Largo
4.97 out of 5 average rating, 192 reviews

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Top guest favorite
The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.
Home in Islamorada
4.97 out of 5 average rating, 208 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

Top guest favorite
A solar and wind powered houseboat is moored on calm waters, featuring bright yellow shutters and a roof deck. Wind turbines and an American flag adorn the top, contrasting with the soothing blue sky and fluffy clouds in the background.
Boat in Islamorada
4.93 out of 5 average rating, 375 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Superhost
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon
4.89 out of 5 average rating, 520 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Top guest favorite
Condo in Tavernier
4.95 out of 5 average rating, 136 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Top guest favorite
The living area features contemporary furnishings and large windows, allowing for bright natural light and views of the waterways. A dining table is positioned beside the seating area. The spacious lanai showcases an outdoor dining setup with a view of the dock and water.
Home in Key Colony Beach
4.95 out of 5 average rating, 131 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Guest favorite
A wooden boardwalk leads to a thatched-roof gazebo, illuminated by soft lighting. The sky displays shades of orange and purple at sunset, reflecting on the calm ocean waters. Navigational markers can be seen along the path, adding to the scenic view.
Condo in Tavernier
4.77 out of 5 average rating, 394 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.

Popular amenities for Islamorada vacation rentals

When is the best time to visit Islamorada?

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Frequently Asked Questions

  • What are the best places to stay in Islamorada?

    Islamorada has a range of guesthouses, private rentals, and waterfront cottages, especially around the marina and near the coastline. Many visitors explore areas close to the water to enjoy snorkeling, local restaurants, and sunset views.

  • What are the best things to do in Islamorada with kids?

    Families frequently enjoy exploring marine life exhibits, interactive aquariums, and sandy beaches. Guided snorkeling tours and paddleboard rentals are also popular ways for kids to discover sea creatures in shallow, clear waters.

  • What are some of the best things to do in Islamorada?

    You can explore local museums, try sport fishing, and visit art galleries. Many visitors also join snorkeling or diving excursions to see vibrant reefs, or enjoy waterfront dining with fresh seafood.

  • How is the weather in Islamorada?

    Islamorada has a tropical climate with winter temperatures around 61–78°F (16–26°C) and summers getting up to 91°F (33°C). Rain is more frequent in late spring and summer, so packing layers and sun protection is often recommended.

  • When is the best time to visit Islamorada?

    Late winter through spring is often suggested for mild temperatures and lower rainfall, making it comfortable for beach activities and outdoor exploration. Summer brings warmer days and more rainfall, along with a vibrant fishing season.

  • What are the best places to visit in Islamorada?

    Islamorada has museums focused on diving and local history, as well as marina areas with waterfront views. Explore artisan shops, marine life centers, and sculpture gardens for a taste of the area's culture.

  • What are some hiking trails in Islamorada?

    You can walk shaded loops through tropical hammock preserves or follow nature trails in local parks. Paths wind past native plants, birdwatching spots, and occasional interpretive signs about the habitat.

  • What are some family activities we can do in Islamorada?

    Families often explore touch tanks at marine centers, kayak calm waters, or join guided eco-tours. Beach picnics and shallow snorkeling are also frequently suggested for groups with children.

  • What are some of the best day trip ideas from Islamorada?

    Many visitors plan outings to nearby state parks, animal sanctuaries, or botanical gardens. Guided boat tours, art village visits, and trips to other islands in the Keys are also frequently suggested.

  • Are there any pet friendly accommodations available in Islamorada?

    Islamorada has pet-friendly rentals, including cottages and beachside homes. Some local parks and waterfront paths also welcome dogs on a leash, making it easier to enjoy the outdoors with your pet.

  • What are some local tips for visiting Islamorada?

    Pack reef-safe sunscreen, as preservation of marine life is prioritized. Local eateries get busy at sunset, and water shoes can help when exploring rocky shorelines or tide pools.

  • What is Islamorada known for?

    Islamorada is known for sport fishing, vibrant coral reefs, and a relaxed Florida Keys atmosphere. Visitors frequently highlight its clear waters, seafood cuisine, and picturesque sunsets.

  • What are the best hidden gems to explore in Islamorada?

    Look for small artists’ studios, tucked-away hammocks with native flora, or local preserves not always on tourist maps. Independent galleries and small historic sites often give a different perspective on the area.

  • What are the best foods to try in Islamorada?

    Islamorada is known for locally caught seafood like yellowtail snapper, stone crab, and Florida lobster. Key lime pie and conch fritters are frequently suggested treats, reflecting flavors of the region.

  • What should I bring for a trip to Islamorada?

    Bring breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for outdoor comfort. Water shoes and a reusable water bottle are helpful for exploring beaches and staying hydrated.

  • What is the nightlife in Islamorada like?

    Nightlife in Islamorada is relaxed, with locally owned bars, seafood spots, and live music venues by the water. Evenings often feature acoustic performances, tropical cocktails, and sunset views.

  • What are the most popular events or festivals in Islamorada?

    Islamorada hosts annual seafood festivals and sport fishing tournaments, with some events timed around winter and spring. Local art walks and culinary celebrations also draw visitors during peak travel periods.

  • Are there family friendly vacation rentals in Islamorada?

    Family-friendly rentals are available throughout Islamorada, including waterfront homes and cottages with outdoor spaces. Many provide convenient access to beaches, playgrounds, and marine activities.

All about Islamorada

Islamorada’s beaches make for a great retreat, but the area is also known for its water sports. Whether you’re an angler looking to go tarpon fishing, an adventurer hoping to go dolphin spotting, or a boater who wants to cruise the backwaters before heading back to the Islamorada Marina’s protected dockage, there’s a getaway with your name on it. Known as the Village of Islands, Islamorada comprises five islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and Indian Key. Approximately halfway between Miami and Key West in the Florida Keys, it’s about 10 miles south of Tavernier, 16 miles south of Key Largo, and 81 miles north of Key West.

What are the top things to do in Islamorada?

Founders Park

This 45-acre park is the most popular of the village’s parks, especially because of its shallow beach on the bay side. In addition to tiki huts, picnic tables, volleyball courts, and a playground, there’s also an Olympic-size pool, walking trails, a driving range, and courts for basketball, tennis, and pickleball.

Windley Key Fossil Reef Geological State Park

Walk along the eight-foot-high walls of the former quarry, formed of Key Largo limestone (fossilized coral). The land was once owned by the Florida East Railroad, a company that helped build the Overseas Railroad in the early 20th century, connecting the mainland to Key West — but it was eventually damaged by hurricanes and shut down.

Alligator Reef Lighthouse

The namesake for the 136-foot-tall lighthouse, built in 1873, is not the reptile, but rather the USS Alligator, whose remains are deep underwater. Nowadays, the area is known for its reef with 500 sea life species, including barracudas and spiny lobsters.

Quick stats about vacation rentals in Islamorada

  • Total vacation rentals

    Explore 800 vacation rentals in Islamorada

  • Nightly prices starting at

    Islamorada vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 8,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    570 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 400 rentals that welcome pets

  • Vacation rentals with a pool

    620 properties feature pools

  • Rentals with dedicated workspaces

    460 properties have a dedicated workspace

  • Wi-Fi availability

    790 of Islamorada vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Gym across Islamorada rentals

  • 4.7 Average rating

    Islamorada stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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