Islamorada vacation rentals
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Top-rated vacation rentals in Islamorada
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Guest suite in Marathon
4.98 out of 5 average rating, 140 reviewsCasa Mariposa: Sombrero Beach Neighborhood
Book your getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, selected as 1 0f 24 amazing AirBNB rentals in the Keys, and 1 of 23 Amazing Airbnbs in The Keys. Step out the door from your private suite to a coral path that leads to our 50' heated/cooled lap pool, waterfall and large patio. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in an other lengths of stay.
May 3 – 10
Condo in Tavernier
4.93 out of 5 average rating, 127 reviewsIt's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba
Stay at our tropical hideaway rated one the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort in the nature isle of Tavernier. You'll love the colorful mid-century modern decor that reflects the shades of this Keys paradise in the American Caribbean. With 60+ pristine acres, Ocean Pointe is the perfect blend of natural beauty and modern-day luxury and convenience for a great couples or small family getaway .
Sep 7 – 14
Guesthouse in Key Largo
4.87 out of 5 average rating, 370 reviewsGuesthouse/Cabin peaceful romantic *sunsets beach.
Guesthouse/Cabin romantic *sunsets beach, docks and fishing pier, on a peaceful lush gardens with private parking to enjoy and relax, surrounded by nature wildlife at its best birds, iguanas, manatees, dolphin’s, eagles only a short walk to the beach and fishing pier, enjoy the immense boats cruising by, relax sipping cocktail. Note a "guesthouse" is part as on a state, small separate dwelling on the grounds of a larger one, used for accommodating guests. *the guesthouse is Not beachfront.
Jun 4 – 11
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Islamorada vacation rentals
Other great vacation rentals in Islamorada
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
Sep 5 – 12
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 81 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
May 3 – 10
Bungalow in Islamorada
4.96 out of 5 average rating, 28 reviewsDream in Paradise! King Master, Queen Guest, Pool
Mar 10 – 17
Cottage in Islamorada
4.97 out of 5 average rating, 63 reviewsIslamorada 2BR, 1BA w/ heated pool and firepit
Nov 28 – Dec 5
Home in Islamorada
5.0 out of 5 average rating, 5 reviewsAnglers Reef Home with Peek-a-Boo Ocean Views
May 13 – 20
Cottage in Islamorada
4.94 out of 5 average rating, 36 reviewsIslamorada bungalow 2 bed & pool
Oct 23 – 30
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Nov 9 – 16
Home in Islamorada
4.93 out of 5 average rating, 14 reviews3 Lux Ensuites Walk/Boat Island!
Jan 18 – 25
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
Oct 12 – 19
Home in Key Largo
4.99 out of 5 average rating, 69 reviewsLittle Cottage on an island
Jun 21 – 28
Home in Islamorada
5.0 out of 5 average rating, 29 reviewsAnglers Reef Islamorada Oceanside 2/2.5+Pool+Beach
Jun 8 – 15
Home in Islamorada
5.0 out of 5 average rating, 8 reviewsHeart of Islamorada ~ Private Boat Slip
Oct 12 – 19
Other great vacation rentals in Islamorada
Home in Islamorada
5.0 out of 5 average rating, 10 reviewsAngler's Reef Gem in Islamorada!
Jan 4 – 11
Camper/RV in Key Largo
4.86 out of 5 average rating, 14 reviewsCozy Waterfront RV in Key Largo w/Boat Slips/Ramp
Oct 8 – 15
Home in Marathon
5.0 out of 5 average rating, 19 reviewsParadise in the Keys
Oct 1 – 8
Home in Marathon
4.9 out of 5 average rating, 52 reviewsBeautiful Beachfront Home w/ Pool/Tiki/Dock
Sep 19 – 26
Home in Duck Key
5.0 out of 5 average rating, 29 reviewsPrivate Pool Tropical Oasis - Centrally Located
Nov 6 – 13
Home in Marathon
5.0 out of 5 average rating, 8 reviewsOceanfront *PARADiSE* Amazing views, pool, dock
Dec 7 – 14
Home in Key Colony Beach
4.98 out of 5 average rating, 44 reviewsCaptain’s Quarters Ahoy Mateys! Florida, Keys
Oct 2 – 9
Condo in Islamorada
5.0 out of 5 average rating, 19 reviewsJust a Few Friends - Ocean View and Bring your Boa
Oct 19 – 26
Home in Marathon
4.85 out of 5 average rating, 20 reviewsP58 - Gulf Front Luxury 4 bedroom 4 bath with priv
Apr 20 – 27
Home in Marathon
5.0 out of 5 average rating, 29 reviews100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
Mar 19 – 26
Home in Key Largo
4.92 out of 5 average rating, 59 reviewsLarge Waterfront Home, w/Efficiency, Pool, Kayaks
Apr 20 – 27
Apartment in Tavernier
5.0 out of 5 average rating, 15 reviewsBeautiful condo with a balcony
Dec 29 – Jan 5
Quick stats about vacation rentals in Islamorada
Total rentals | 810 properties |
---|---|
Rentals with a pool | 630 properties have a pool |
Pet-friendly rentals | 400 properties allow pets |
Family-friendly rentals | 580 properties are a good fit for families |
Total number of reviews | 5.6K reviews |
Nightly prices starting at | G$8,375 GYD before taxes and fees |
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.
Are there pet-friendly vacation rentals in Islamorada?
Four-legged friends are welcome in Islamorada. Choose from more than 400 vacation rentals for guests traveling with pets.
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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