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 favorite

Guest suite in Marathon

4.98 out of 5 average rating, 140 reviews

Casa 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

G$40,699 GYD per night
Guest favorite

Condo in Tavernier

4.93 out of 5 average rating, 127 reviews

It'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

G$49,535 GYD per night
Guest favorite

Guesthouse in Key Largo

4.87 out of 5 average rating, 370 reviews

Guesthouse/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

G$42,914 GYD per night

Popular amenities for Islamorada vacation rentals

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
Bud N' Mary's Marina19 locals recommend
Florida Keys Dive Center11 locals recommend

Other great vacation rentals in Islamorada

Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Sep 5 – 12

G$56,786 GYD per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

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

May 3 – 10

G$37,648 GYD per night
Guest favorite

Bungalow in Islamorada

4.96 out of 5 average rating, 28 reviews

Dream in Paradise! King Master, Queen Guest, Pool

Mar 10 – 17

G$166,209 GYD per night
Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 63 reviews

Islamorada 2BR, 1BA w/ heated pool and firepit

Nov 28 – Dec 5

G$82,430 GYD per night
Superhost

Home in Islamorada

5.0 out of 5 average rating, 5 reviews

Anglers Reef Home with Peek-a-Boo Ocean Views

May 13 – 20

G$68,045 GYD per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 36 reviews

Islamorada bungalow 2 bed & pool

Oct 23 – 30

G$90,239 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Nov 9 – 16

G$117,186 GYD per night
Guest favorite

Home in Islamorada

4.93 out of 5 average rating, 14 reviews

3 Lux Ensuites Walk/Boat Island!

Jan 18 – 25

G$119,482 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct 12 – 19

G$163,295 GYD per night
Guest favorite

Home in Key Largo

4.99 out of 5 average rating, 69 reviews

Little Cottage on an island

Jun 21 – 28

G$36,180 GYD per night
Guest favorite

Home in Islamorada

5.0 out of 5 average rating, 29 reviews

Anglers Reef Islamorada Oceanside 2/2.5+Pool+Beach

Jun 8 – 15

G$96,635 GYD per night
Guest favorite

Home in Islamorada

5.0 out of 5 average rating, 8 reviews

Heart of Islamorada ~ Private Boat Slip

Oct 12 – 19

G$195,917 GYD per night

Other great vacation rentals in Islamorada

Guest favorite

Home in Islamorada

5.0 out of 5 average rating, 10 reviews

Angler's Reef Gem in Islamorada!

Jan 4 – 11

G$87,247 GYD per night
Superhost

Camper/RV in Key Largo

4.86 out of 5 average rating, 14 reviews

Cozy Waterfront RV in Key Largo w/Boat Slips/Ramp

Oct 8 – 15

G$30,848 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 19 reviews

Paradise in the Keys

Oct 1 – 8

G$181,955 GYD per night
Guest favorite

Home in Marathon

4.9 out of 5 average rating, 52 reviews

Beautiful Beachfront Home w/ Pool/Tiki/Dock

Sep 19 – 26

G$145,135 GYD per night
Guest favorite

Home in Duck Key

5.0 out of 5 average rating, 29 reviews

Private Pool Tropical Oasis - Centrally Located

Nov 6 – 13

G$125,580 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Oceanfront *PARADiSE* Amazing views, pool, dock

Dec 7 – 14

G$199,345 GYD per night
Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 44 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Oct 2 – 9

G$51,685 GYD per night
Guest favorite

Condo in Islamorada

5.0 out of 5 average rating, 19 reviews

Just a Few Friends - Ocean View and Bring your Boa

Oct 19 – 26

G$61,711 GYD per night
Superhost

Home in Marathon

4.85 out of 5 average rating, 20 reviews

P58 - Gulf Front Luxury 4 bedroom 4 bath with priv

Apr 20 – 27

G$124,672 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 29 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Mar 19 – 26

G$140,831 GYD per night
Guest favorite

Home in Key Largo

4.92 out of 5 average rating, 59 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Apr 20 – 27

G$59,492 GYD per night
Guest favorite

Apartment in Tavernier

5.0 out of 5 average rating, 15 reviews

Beautiful condo with a balcony

Dec 29 – Jan 5

G$38,589 GYD per night

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.

Destinations to explore

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