
Vacation rentals in Islamorada
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Popular amenities for Islamorada vacation rentals
Condo rentals in Islamorada

1BR - Key Largo Sun & Sand Hideaway
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.

Reel Large END Unit in Ocean Point Suites
Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.

Your Happy Place - Oceanfront
Sandra’s place was beautiful and she was a wonderful host. She was proactive in giving us all the information we needed to settle in AND also providing wonderful recommendations to restaurants around the area (three of which we tried and thoroughly enjoyed). Very responsive to any questions we had regarding locations of certain items or locations. The place itself was very cozy and homey. Felt very comfortable relaxing there in such a serene environment. Will gladly take an opportunity to stay here again.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again

Waterfront Spacious Condo Key Largo #4, 10% Off 7+
Javier’s place was as expected. The balcony over looking the canal was awesome. We saw lots a cool fish, a turtle and even a manatee swim right up. The property abuts dolphin plus, where you can swim with dolphins and there is a cute coffee trailer Cuppacobanna situated in the parking lot, has a great Churro latte. Right across the street is the Fish Market. A hidden gem for sure! Walk right over and you can order at the window and sit on the water or at their outside bar. We walked over to the dock at the market and saw tons of nursing sharks just hanging out. We were in town for a wedding at Dream Bag Resort which was only 3 minutes away. Great location, super convenient. Although beds and everything were super clean, I would suggest new comforters which someone previously stained. Also one back cushion missing from the outside patio chairs. We did not need to cook at all so hard to judge that aspect. Not an over abundance of kitchen supplies but the basics. Great stay!

Ocean Blue Condo, Key Colony Beach Heated Pool
We enjoyed staying at Kim’s place. It was nice having the pool and private beach within just a few steps….so relaxing that you could easily spend all your time there. The unit was very clean and comfortable.

Key Largo Sunrise Resort Style Ocean Pointe 5315
The condo was pristine and actually better than the photos. Bedrooms in particular were really lovely. Our only issue was that the WiFi was out but Sean was super responsive in getting it back up. Plus there was a common WiFi for the building which worked fine. I would definitely rent again.

Beachside Unit 37 - Come Relax on the Atlantic!
This is located in a great area of Marathon, Fl . A nice and safe area . The building is older but it has been updated and looks great. The beach area is awesome, a very nice beach with lots of sand with a few steps down to the ocean , this is a great private beach
Pet-friendly vacation rentals in Islamorada

Waterfront Cozy Cottage with Boat Ramp & Dock!
Wish we could’ve stayed longer. It was a perfect home!

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!

The Pink Dolphin House.
Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.

Paradise Cove!30ft Dock Pool BBQ
Loved our rental in Key Colony. The house was beautiful and the kids loved the private pool. The place felt just like home.

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club
Our family of 8 stayed for a week and found the accommodations absolutely perfect. The beds were comfortable and clean. I loved the ceiling fans and feeling the ocean breeze through the sliding screen door at night. Plenty of closet space to unpack and the outdoor living area was a dream. We played shuffleboard and grilled out a lot. Excellent lounge chairs made stargazing a delight. Great shower pressure and plenty of towels provided. Washer and dryer worked well, as did all of the kitchen appliances. Only 3 out of the 4 bikes were useable; one of them needs a tune up; handlebars were loose and made riding unsafe. Be warned there are no bike helmets. We didn’t use the paddle boards or kayaks because it was a very windy week and the current was strong but they looked to be in good repair and there were multiple life jackets and water shoes and pool noodles available. Loved the pool and beach access at the clubhouse!

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
The four of us arrived at Mary’s place and we immediately felt right at home. The place was neat and clean and the decor was tropical. The backyard overlooking the canal was a great place to relax and unwind. We loved walking down the block to the Cabana club each afternoon after coming back from local excursions. One of the great benefits was being able to use the Cabana club which had a fantastic pool, hot tub, beach access and a full service bar with great food and drinks with excellent service and a friendly staff!

Waterfront w/pool and hot tub
We had a great time at this location. They had everything we needed and Key Colony is a perfect spot to vacation.

Vibrant Beachfront Villa
Had a wonderful wonderful weekend. Would highly recommend this unit!
Pet-friendly condominiums in Islamorada

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Gorgeous lagoon-front 2BR Townhouse with 2 pools
The home was immaculate, all the necessary dishes, pans, appliances. There were no extras such as coffee filters or cooking oils etc. The setting was very beautiful and well maintained and many amenities. It is a family friendly community with multiple young children. Location near restaurants and activities was great. And we really enjoyed the screened in porch. Thanks!

Seashells Getaway - Boat Slip, Ramp, Pool
Hello. We Booked this place so I could be in the sun on a lounge chair and husband could fish. It was exactly what we wanted. We were able to hang out together and both get what we wanted. He caught fish like crazy! Place is beautiful and exactly how described. Getting an Uber/lyft was easy. Sombrero Beach was beautiful. Ana was excellent to communicate with. Condo bed was very comfy and the bedroom dark. The use of a cooler and beach chairs was appreciated. Would not hesitate to book again.

Oceanside Key Largo 3/3 kayaks included
Very comfortable home with every amenity you could need. The location was great and the condo complex had an awesome lagoon with bunches of fish. Bikes and kayaks available for use and plenty of beach and pool towels. Central to a bunch of restaurants and Rich gave me great recommendations. He was very communicative throughout and would answer promptly when we had any questions. Great stay!

Key Largo Condo
This condo was everything it said it was. Very clean. Great location, clean and serviceable furnishings and an awesome view. One thing that really struck out for me was that the kitchen had everything that you would need without being stuffed with a lot of extra stuff you don’t need. Also the pots and pans were very clean and almost new. Michael was very responsive to all our questions and made sure that we were happy with everything. We would definitely stay here again and recommend it to anyone interested in staying in Key Largo.

key Largo 3 Bedroom Townhouse Gated Community
Everything was great! Nice area, and easy access to local activities. we enjoyed our stay.

Hidden Key Hideout
Such a lovely location along a creek with access to kayaks. We enjoyed taking them out and just watching the water from the balcony. The place had everything we needed and was a short distance from Key Largo.
Quick stats about vacation rentals in Islamorada
Total rentals
880 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
7.6K reviews
Family-friendly rentals
610 properties are a good fit for families
Pet-friendly rentals
420 properties allow pets
Rentals with a pool
610 properties have a pool
Your guide to Islamorada
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.
The best time to stay in a vacation rental in Islamorada
Summertime in the Keys and the living is easy — but scorching hot. High temperatures are in the upper 80s to 90s Fahrenheit, while lows hover around the mid-70s. Along with the warm weather comes humidity, which can often feel oppressive, so opt for lightweight, comfortable clothing. Hurricane season runs from June through November, so keep an eye on the forecast, since there is only one road in and out of the Keys, and you’ll want to plan ahead if conditions get extreme. Spring and fall may be the more comfortable times of year to visit, when it’s between the upper 60s and 80s. But winters are also lovely in the mid-60s to upper 70s — and with less rain.
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.
Frequently Asked Questions
How is the weather in Islamorada?
Islamorada has a tropical climate with warm temperatures year-round. In the summer, temperatures can reach 90°F (32°C), while winters are mild, with highs around 75°F (24°C). Rain is common from May to October, with September being the wettest month.
What are some of the best things to do in Islamorada?
Popular activities in Islamorada include snorkeling and scuba diving at the Alligator Reef, fishing in the clear blue waters, and exploring the Indian Key Historic State Park. Visitors also frequently enjoy paddle boarding, biking, and kayaking.
What is the best time of year to visit Islamorada?
The most popular time to visit Islamorada is from December to April when the weather is mild and dry. During this period, the island often hosts various events such as the Island Fest in April, which features art, food, and music.
What are the best places to stay in Islamorada?
Popular areas to stay in Islamorada include the centrally-located Islamorada Village, which has easy access to restaurants and shops. The quieter Lower Matecumbe Key is also frequently suggested for its beautiful beaches and easy access to Anne's Beach.
What are the best places to visit in Islamorada?
Popular places to visit in Islamorada include the History of Diving Museum, Anne's Beach, Theater of the Sea, and the Rain Barrel Sculpture Gallery. Visitors often explore Lignumvitae Key Botanical State Park and Indian Key Historic State Park as well.
What are some hiking trails in Islamorada?
While Islamorada is more famous for its water activities, it also has some enjoyable walking trails. The Windley Key Fossil Reef Geological State Park has several short trails that feature unique geological formations and the Indian Key Historic State Park has a walking path with interpretive signs about local history.
What are some family activities to do in Islamorada?
Families in Islamorada often enjoy exploring the Theater of the Sea, the History of Diving Museum, and the Windley Key Fossil Reef Geological State Park. A visit to the Dolphin Research Center or the Florida Keys Wild Bird Rehabilitation Center can also be a rewarding experience for children and adults alike.
What are some of the best day trip ideas in Islamorada?
Day trips from Islamorada often involve visiting the nearby Key Largo or Marathon islands, both perfect for snorkeling and wildlife watching. The vibrant city of Miami is just 1.5 hours (130 km) away and exploring the Everglades National Park is also a feasible day trip.
What types of vacation rentals are available in Islamorada?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Islamorada. From over 330 house rentals to over 90 condo rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Islamorada?
Yes! Work meets play with ease at over 490 vacation rentals in Islamorada featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
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- Coral Castle
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