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Holiday rentals in Islamorada

Find and book unique accommodation on Airbnb

Top-rated holiday 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

5–12 Sept

£248 per night
Guest favourite

Flat 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.

6–13 Dec

£154 per night
Guest favourite

Guest house 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.

4–11 Jun

£183 per night

Popular amenities for Islamorada holiday 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 holiday rentals in Islamorada

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 44 reviews

The Paradise 2

2–9 Feb

£309 per night
Guest favourite

Cottage in Islamorada

4.97 out of 5 average rating, 63 reviews

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

5–12 Aug

£368 per night
Guest favourite

Cottage in Islamorada

4.94 out of 5 average rating, 36 reviews

Islamorada bungalow 2 beds & pool

23–30 Oct

£382 per night
Superhost

Home in Islamorada

5.0 out of 5 average rating, 5 reviews

Anglers Reef Home with Peek-a-Boo Ocean Views

13–20 May

£320 per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

9–16 Nov

£528 per night
Guest favourite

Home in Islamorada

4.93 out of 5 average rating, 14 reviews

3 Lux Ensuites Walk/Boat Island!

18–25 Jan

£517 per night
Guest favourite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

12–19 Oct

£746 per night
Guest favourite

Home in Key Largo

4.99 out of 5 average rating, 69 reviews

Little Cottage on an island

17–24 Jun

£156 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

8–15 Jun

£437 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

17–24 Sept

£482 per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

8–15 Jun

£150 per night
Guest favourite

Tiny home in Key Largo

4.98 out of 5 average rating, 57 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

4–11 Oct

£255 per night

Quick stats about holiday 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

£32 before taxes and fees

Destinations to explore

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