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.

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Guest favorite

Apartment in Tavernier

4.89 out of 5 average rating, 432 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Capt. Craig’s Guest Quarters The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.

Nov 12 – 19

ﺩ.ﺇ730 per night

Guest favorite

Home in Islamorada

5.0 out of 5 average rating, 12 reviews

Angler's Reef Gem in Islamorada!

Welcome to 128 Anglers Way: "Morada Daydreaming". This house has 2 bedrooms upstairs, each with its own full bath and private balcony. A washer/dryer combo is conveniently located upstairs. The main level open floor plan features peek a boo ocean views. It also contains a half bath and a fully stocked kitchen. An outdoor seating area and gas grill is provided. Includes 2 assigned parking spaces. Angler's Reef is a premier resort style community with a heated pool, kayaks, and paddle boards.

Nov 9 – 16

ﺩ.ﺇ1,446 per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing 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, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Jul 4 – 11

ﺩ.ﺇ798 per night

Guest favorite

Apartment in Key Largo

4.94 out of 5 average rating, 246 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!

Dec 7 – 14

ﺩ.ﺇ666 per night

Guest favorite

Cottage in Islamorada

4.85 out of 5 average rating, 124 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Aug 4 – 11

ﺩ.ﺇ718 per night

Guest favorite

Home in Islamorada

4.97 out of 5 average rating, 164 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.

Dec 7 – 14

ﺩ.ﺇ967 per night

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 325 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.

Nov 26 – Dec 3

ﺩ.ﺇ686 per night

Guest favorite

Apartment in Tavernier

5.0 out of 5 average rating, 15 reviews

Beautiful condo with a balcony

Newly Renovated Beach Décor unit! Breathtaking views of the protected Florida Keys mangroves. Heated Olympic size pool/jacuzzi with fully equipped bar and bartender. Tennis courts recently renovated. Walking paths through the Florida Keys protected mangroves. Onsite marina, with beach, gazebo, dockage ramp. Restaurant with ocean views. Snorkeling and kayak on the premises. Walk to the end of the pier and take in the ocean breeze and watch the boats sail by.

Nov 8 – 15

ﺩ.ﺇ681 per night

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 122 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Sep 17 – 24

ﺩ.ﺇ1,139 per night

Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 65 reviews

Key Lime Cottage 2br 1ba w/pool

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!

Mar 22 – 29

ﺩ.ﺇ1,609 per night

Guest favorite

Bungalow in Islamorada

4.97 out of 5 average rating, 29 reviews

Dream in Paradise! King Master, Queen Guest, Pool

Castaway Island! Luxury In paradise! This hidden gem is your piece of paradise waiting! Fully remodeled and furnished from the floor up. All new furniture, fixtures and furnishings await. One of the most well appointed and private Bungalows in Islamorada. Perfect for the honeymooners and special occasion couples and small families. Private outside spaces. 4 Bikes, 2 ultra lite SUP's, 2 Kayaks, 4+ beach chairs, ice chests and more await you.

Aug 19 – 26

ﺩ.ﺇ2,315 per night

Guest favorite

Guesthouse in Key Largo

4.91 out of 5 average rating, 186 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Mar 27 – Apr 3

ﺩ.ﺇ743 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Islamorada vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Islamorada's top sights

Theater of the Sea140 locals recommend

Islander Resort3 locals recommend

Robbie's165 locals recommend

Rain Barrel Village21 locals recommend

Florida Keys Dive Center11 locals recommend

Bud N' Mary's Marina19 locals recommend

Other great vacation rentals in Islamorada

Guest favorite

Home in Islamorada

4.94 out of 5 average rating, 16 reviews

3 Lux Ensuites Walk/Boat Island!

Mar 15 – 22

ﺩ.ﺇ2,096 per night

Guest favorite

Home in Key Largo

4.99 out of 5 average rating, 73 reviews

Little Cottage on an island

Jul 18 – 25

ﺩ.ﺇ635 per night

Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

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

May 25 – Jun 1

ﺩ.ﺇ708 per night

Guest favorite

Home in Islamorada

5.0 out of 5 average rating, 15 reviews

Pristine pool front home w/ocean views Anglers 148

Aug 15 – 22

ﺩ.ﺇ1,864 per night

Guest favorite

Cottage in Islamorada

4.95 out of 5 average rating, 39 reviews

Islamorada bungalow 2 bed & pool

Jan 25 – Feb 1

ﺩ.ﺇ2,044 per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

The Gulf Cottage at Marathon Key

Jul 6 – 13

ﺩ.ﺇ479 per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 32 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Mar 22 – 29

ﺩ.ﺇ2,315 per night

Guest favorite

Home in Islamorada

4.96 out of 5 average rating, 55 reviews

Tropical Getaway 3/3 with 100’ boat dock and pool

Sep 20 – 27

ﺩ.ﺇ1,908 per night

Show all

Other great vacation rentals in Islamorada

Guest favorite

Home in Key Largo

5.0 out of 5 average rating, 46 reviews

The Paradise 2

Nov 3 – 10

ﺩ.ﺇ1,495 per night

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Oceanfront *PARADiSE* Amazing views, pool, dock

Sep 14 – 21

ﺩ.ﺇ3,688 per night

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 20 reviews

Paradise in the Keys

Jun 3 – 10

ﺩ.ﺇ3,191 per night

Guest favorite

Condo in Tavernier

4.98 out of 5 average rating, 63 reviews

Sugar Cane - Florida Keys tropical retreat

Jun 25 – Jul 2

ﺩ.ﺇ759 per night

Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Nov 24 – Dec 1

ﺩ.ﺇ996 per night

Guest favorite

Home in Tavernier

4.96 out of 5 average rating, 55 reviews

Sunset Beach Hideaway *Private Beach* *Jacuzzi*

Dec 14 – 21

ﺩ.ﺇ4,065 per night

Guest favorite

Camper/RV in Key Largo

4.97 out of 5 average rating, 39 reviews

paradise point, ocean front /dock/ramp.

Aug 11 – 18

ﺩ.ﺇ691 per night

Guest favorite

Home in Duck Key

5.0 out of 5 average rating, 30 reviews

Private Pool Tropical Oasis - Centrally Located

Nov 25 – Dec 2

ﺩ.ﺇ2,500 per night

Show all

Quick stats about vacation rentals in Islamorada

Total rentals	830 properties
Rentals with a pool	640 properties have a pool
Pet-friendly rentals	400 properties allow pets
Family-friendly rentals	590 properties are a good fit for families
Total number of reviews	6.1K reviews
Nightly prices starting at	ﺩ.ﺇ147 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 510 vacation rentals in Islamorada featuring dedicated workspaces. Stay connected and productive in your home away from home.

Islamorada vacation rentals

Top-rated vacation rentals in Islamorada

Vacation rentals for every style

Bungalows

Villas

Houses

Popular amenities for Islamorada vacation rentals

Stay near Islamorada's top sights

Other great vacation rentals in Islamorada

Home in Islamorada

Home in Key Largo

Guest suite in Key Colony Beach

Home in Islamorada

Cottage in Islamorada

Home in Marathon

Home in Marathon

Home in Islamorada

Other great vacation rentals in Islamorada

Home in Key Largo

Home in Marathon

Home in Marathon

Condo in Tavernier

Cottage in Islamorada

Home in Tavernier

Camper/RV in Key Largo

Home in Duck Key

Quick stats about vacation rentals in Islamorada

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Your guide to Islamorada

All About Islamorada

The best time to stay in a vacation rental in Islamorada

Top things to do in Islamorada

Founders Park

Windley Key Fossil Reef Geological State Park

Alligator Reef Lighthouse

Frequently Asked Questions

How is the weather in Islamorada?

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

What is the best time of year to visit Islamorada?

What are the best places to stay in Islamorada?

What are the best places to visit in Islamorada?

What are some hiking trails in Islamorada?

What are some family activities to do in Islamorada?

What are some of the best day trip ideas in Islamorada?

Are there pet-friendly vacation rentals in Islamorada?

Are there vacation rentals with a dedicated workspace in Islamorada?

Destinations to explore