Vacation rentals in Islamorada

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Top-rated vacation rentals in Islamorada

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Top guest favourite
A wide balcony overlooks a serene harbor, featuring several boats docked in the water. Two tall chairs are positioned against the railing, offering a view of the vibrant blue sky and surrounding marina.
Home in Key Largo
4.98 out of 5 average rating, 227 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Top guest favourite
An aerial view of a large pool area, surrounded by lounge chairs and umbrellas in vibrant colors. Lush greenery and trees border the space, while the ocean can be seen in the distance. A hot tub is positioned near the pool, enhancing the resort-like setting.
Condo in Tavernier
4.9 out of 5 average rating, 311 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Guest favourite
An open-concept living area features a comfortable sofa and loveseat, designed for relaxation. A stylish dining table accommodates four. A wall-mounted TV and electric fireplace add modern touches, while large sliding glass doors offer natural light and views of the surrounding landscape.
Condo in Tavernier
4.95 out of 5 average rating, 165 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Top guest favourite
A wooden dock extends over calm waters, flanked by white pilings and gently swaying palm trees. The warm hues of twilight fill the sky, reflecting softly on the water's surface, creating a serene atmosphere perfect for evening relaxation.
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 125 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Guest favourite
A scenic view captures the marina lined with docked boats, extending towards the sparkling turquoise waters of the Atlantic Ocean. Lush mangroves frame the waterway, while a clear sky with scattered clouds creates a tranquil coastal atmosphere.
Condo in Tavernier
4.89 out of 5 average rating, 157 reviews

1BR - Key Largo Sun & Sand Hideaway

Welcome to Key Largo Sun & Sand Hideaway, where relaxation awaits in the beautiful Florida Keys. Our fully equipped one-bed, one-bath suite is the ideal destination for your next vacation. Nestled within an oceanfront resort, you'll enjoy access to a private beach, marina and other amenities. Indulge in a serene coastal experience just minutes away from restaurants, shopping, and other exciting water activities. Unwind, rejuvenate, and create unforgettable memories in this tropical paradise.

Superhost
Guesthouse in Key Largo
4.85 out of 5 average rating, 490 reviews

Romantic cozy peaceful Guesthouse beach Sunsets.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

Top guest favourite
Home in Islamorada
4.97 out of 5 average rating, 206 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 favourite
Vibrant bougainvillea flowers in shades of pink and deep red create a lush display against the greenery. The dense foliage adds a natural texture, while drops of water may suggest recent rainfall, enhancing the overall freshness of the scene.
Guesthouse in Key Largo
4.93 out of 5 average rating, 198 reviews

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

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, 497 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!

Guest favourite
A serene pool area is surrounded by lush tropical plants and swaying palm trees under a clear blue sky. A large blue umbrella provides shade over a lounging area, enhancing the inviting atmosphere of the outdoor space.
Cottage in Islamorada
4.97 out of 5 average rating, 132 reviews

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Guest favourite
Condo in Tavernier
4.92 out of 5 average rating, 155 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!

Top guest favourite
Home in Key Largo
4.9 out of 5 average rating, 438 reviews

Your Keys Getaway!

Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.

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.

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 $55 CAD 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 and 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

  • Wifi availability

    790 of Islamorada vacation rentals include wifi 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

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada