Islamorada Vacation Rentals & House Rentals - 57 Rentals Available

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1 / 22

Islamorada Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
"My husband and I had the pleasure of staying at this beautiful condo. The views were amazing. We used the pool daily and was a great place to relax. The owners made sure every last detail was taken care of. Love this condo!"
- Anne Sullivan, Chicago
(1) Excellent (1 review)
1 / 29

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Not more I can say except we all had a great time and thanks to the hosts and location this was an amazing celebration! Definately recommend!"
- Andrew Dick, Tacoma, WA
(10) Excellent (10 reviews)
1 / 9

Islamorada Townhouse
2 BR / 2.5 BA / Sleeps 4 2 4 7 night min stay
Townhouse / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Microwave • Air Conditioning
"What a great place to stay Perfect for boating, fishing or just relaxing - cant wait to go back!"
- Rob Apostolakis, Chicago, IL
(6) Excellent (6 reviews)
1 / 15

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 30 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property."
- Key Rosser, Bradenton,Fl
(9) Excellent (9 reviews)
1 / 6

Islamorada Home
2 BR / 1 BA / Sleeps 5 2 5 30 night min stay
Home / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
"Thank you Robert and Joan for the use of your rental home in Islamorada! My husband and two daughters had an enjoyable week long vacation staying here. There is plenty of space, comfort, and amenities! The couple staying downstairs were also very ..."
- Tiffany Davis, Haverford, PA
(4) Excellent (4 reviews)
1 / 29

Islamorada Home
3 BR / 3 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This house is the best! ! ! ! ! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own..."
- Shannon Smiles, Wilmington, NC
(21) Excellent (21 reviews)
1 / 17

Islamorada Home
4 BR / 3 BA / Sleeps 12 4 12 30 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"We have stayed at this home 2 years in a row and have enjoyed ourselves tremendously! It has a great location at the end of the street, corner lot, pool privacy, and water front. The house is large enough to accomodate our large family and give privacy..."
- julie forbush, Michigan
(18) Excellent (18 reviews)
1 / 9

Islamorada Home
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"What a lovely place. Immaculately clean and beautifully appointed. Everything as advertised and the pool and hot tub are beautiful. Nicely situated in Lower Metacumbe. The private beach was a gorgeous addition.We had a wonderful time and Capt. Mark..."
- Bryan Loveless, Columbus, Ohio
(7) Excellent (7 reviews)
1 / 6

Islamorada Townhouse
3 BR / 2 BA / Sleeps 6 3 6 30 night min stay
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The location is perfect! It is very orivate with an amazing view. The condo is in pristine condition! We will definitely come again!"
- Caroline McCurry, South Carolina
(7) Excellent (7 reviews)
1 / 12

Islamorada Condo
2 BR / 2 BA / Sleeps 5 2 5 Min stay varies
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
Dishwasher • Microwave • Air Conditioning
"Condo is quiet and private, large balcony and view was spectacular. Clean and well stocked. Plenty of room for 5. Owner easily available by text or email, Would highly recc for others"
- bev nelson, gainesville, florida
(21) Excellent (21 reviews)
1 / 28

Islamorada Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We enjoy coming back, weather just great. Just so relaxing. Chiki bar, pool, private dock all a plus. Est place to vacation."
- Joan Geissler, Lake Worth, Florida USA
(3) Excellent (3 reviews)
1 / 9

Islamorada Home
4 BR / 4 BA / Sleeps 8 4 8 full period
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Microwave • Air Conditioning
"We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better, we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish, we caught ..."
- Lynne Kersey Coffey, Deland Florida
(7) Excellent (7 reviews)
1 / 16

Islamorada Condo
2 BR / 2.5 BA / Sleeps 4 2 4 No min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The house was so nice, everything you could possible need. The view from the lanai is superb, Bobbie was a great owner, would answer your call for anything. The complex is quiet, and the people are friendly. What an amazing vacation! !"
- Denise McDade, central coast california
(1) Excellent (1 review)
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About Islamorada

Islamorada consists of a “Village of Islands” spread out over six islands in the Florida Keys. Surrounded by cerulean ocean waters and soft sands, this destination is a tropical paradise for those looking to get away from it all. Stay in oceanfront Islamorada vacation rentals for the ultimate convenience during your beach getaway.

Climate

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s, and the ocean waters provide a refreshing respite. Pack lots of sunscreen as the sun’s rays are much stronger than they are in northern parts of the U.S. Wintertime brings temperatures in the 70s – cool by Florida standards, but still comfortably warm for vacationers from other parts of the country.

Transit 

Islamorada is best traveled by car or boat. Fly into Miami International Airport or Key West International Airport then rent a car to travel to Islamorada. The island roads are scenic and views from the bridges connecting each island are breathtaking. Just keep in mind that speed limits are strictly enforced in the Florida Keys. Once you’ve arrived, ditch the car and island hop via boat. Rent a boat from Islamorada Watersports Company and spend time cruising the pristine waters.

Things to Do

Islamorada is well-known as the sport fishing capital of the world, and the surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Embark on a fishing charter led by a knowledgeable captain from Sea Horse Private Charters or Drop Back Fishing Charters for a fun day out on the water. If you’d rather stay on land, explore try fly fishing in the backcountry.

There’s much to see and do in Islamorada besides fishing, though. Soak up sun with the family at Anne’s Beach. Here, there are many coves along the white sands, making it easy to find a quiet, private for the family, and the surrounding mangroves provide an ideal setting to observe Florida marine life. The beach also has shallow waters, and it is a popular destination for kite-boarders. Visit the Theater of the Sea, so everyone can swim with dolphins, interact with sea lions and turtles, and enjoy live snorkeling tours that the park provides.
 
San Pedro Underwater Archaeological Preserve State Park is a historical shipwreck site and a popular diving adventure for visitors. The 18-feet deep waters at this site are best for experienced divers, but divers of all levels will enjoy exploring nearby coral reefs underwater. Another popular attraction is the Windley Key Fossil Reef Geological State Park, which includes nature trails for hiking and features fossilized coral. There are picnic tables and educational tours for kids, and the park is home to a variety of birds and native wildlife.

Events

With ideal weather year-round, the fun never stops and Islamorada hosts events and activities to keep families entertained all year long. Visit in January for the Annual Blessing of the Fleet to kick off another year of fishing. In March, stroll throughout Islamorada during National Wildlife Week or visit the weekly farmer’s market open on Fridays. The summer brings a lively 4th of July celebration, the Spirit of Islamorada as well as numerous weekly events, while winter also brings fun holiday activities and festivals.

This island oasis beckons to vacationers all year long with its divine weather and laidback atmosphere. Islamorada vacation rentals provide easy access to the abundance of water activities without giving up comfort or any of the necessities for the perfect stay. You might even thinking about making Islamorada your permanent home.