Vacation rentals in Islamorada

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Islamorada

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage. Short walk to world famous Lorelei for sunset celebrations. Custom length of stays can be arranged if booking a sandbar/sunset/fishing charter with our family business. The cottage was built in 1940s and still has the original hardwood floors, open beam ceilings. Private yet in the heart of Islamorada. Walk to two local craft breweries nearby! This listing is new to AIRBNB but booked for many reservations thru VRBO all 5 star. One pet only under 20lbs. /pet fee $150

Sep. 5 – 12

$424 CAD per night
Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 144 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Capt. Craig’s Guest Quarters The Seahorse 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.

Dec. 6 – 13

$264 CAD per night
Guest favourite

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

$313 CAD 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 favourite

Home in Key Largo

5.0 out of 5 average rating, 43 reviews

The Paradise 2

Feb. 2 – 9

$533 CAD per night
Guest favourite

Cottage in Islamorada

4.97 out of 5 average rating, 63 reviews

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

Aug. 5 – 12

$624 CAD per night
Guest favourite

Cottage in Islamorada

4.94 out of 5 average rating, 36 reviews

Islamorada bungalow 2 bed & pool

Oct. 23 – 30

$655 CAD 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

$548 CAD per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Nov. 9 – 16

$905 CAD per night
Guest favourite

Home in Islamorada

4.93 out of 5 average rating, 14 reviews

3 Lux Ensuites Walk/Boat Island!

Jan. 18 – 25

$885 CAD per night
Guest favourite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct. 12 – 19

$1,278 CAD per night
Guest favourite

Home in Key Largo

4.99 out of 5 average rating, 69 reviews

Little Cottage on an island

Jun. 17 – 24

$267 CAD per night
Guest favourite

Home in Islamorada

5.0 out of 5 average rating, 29 reviews

Anglers Reef Islamorada Oceanside 2/2.5+Pool+Beach

Jun. 8 – 15

$750 CAD per night
Guest favourite

Home in Islamorada

4.96 out of 5 average rating, 55 reviews

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

Sep. 17 – 24

$826 CAD per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun. 8 – 15

$257 CAD per night
Guest favourite

Tiny homes in Key Largo

4.98 out of 5 average rating, 57 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Oct. 4 – 11

$437 CAD 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

$54 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada