Holiday Rentals in Islamorada

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Islamorada

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (114)
"The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back."
United States
Tracie
Treasure Harbor

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (575)
"Best hotel for the price"
United States
luzdari
The price is €111
includes taxes & fees
30 Nov - 1 Dec
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (69)
"Great for family vacation with kids. love it"
United States
Dixania
The price is €726
includes taxes & fees
30 Nov - 1 Dec
The Islands of Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Matecumbe
9.6 out of 10, Exceptional, (32)
"Nice and convenient location. "
United States
Daniel D.
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Matecumbe
10.0 out of 10, Exceptional, (86)
"Wonderful place to stay for families. We loved it. Rooms and bathrooms were fantastic. Michele was a great host that made sure our stay was perfect. "
United States
Kimber T.
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

Islamorada
9.8 out of 10, Exceptional, (34)
"We had a great family trip! The house was perfect and so comfortable "
United States
Cheryl J.
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada
10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
United States
Isabella
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Matecumbe
9.6 out of 10, Exceptional, (86)
"Great property and great location!"
United States
Anonymous traveller
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

Islamorada
10.0 out of 10, Exceptional, (200)
"This was a perfect place for two couples. The house was lovely, the pool was perfect and everyone was so friendly. Craig's place was clean and comfortable. He was easy to communicate with and did everything to make our stay five stars! Would definitely recommend this home "
United States
Anonymous traveller
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

Venetian Shores
10.0 out of 10, Exceptional, (38)
"We enjoyed our stay so much. This house was a dream. It had all we need to make out keys getaway unforgettable! "
United States
Milena P.
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Matecumbe
9.2 out of 10, Wonderful, (16)
"We love to stay in these cottages in Islamorada! This cottage was very clean, did a great job with organizing and creating extra space for storage, and was beautifully decorated! It was perfect for our family of 4. We enjoyed the pool as well which is clean and nicely accessorized with lots of seating and umbrellas. We will definitely be returning to this cottage! "
United States
Nicole L.
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

BeachFront Paradise/By The Glam Homes

Matecumbe
10.0 out of 10, Exceptional, (1)
"Professional communication with the host. Great pool. Enough beds to sleep everyone comfortably. Loved having the second fridge too."
United States
Alex F.
BeachFront Paradise/By The Glam Homes

Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

Islamorada
9.8 out of 10, Exceptional, (153)
"very nice property. Some minor issues, but in total a great week."
United States
Darrell P.
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

Islamorada Boaters Paradise with 70' Dock and private beach access..

Matecumbe
10.0 out of 10, Exceptional, (24)
"Everything was amazing for our stay. We were able to have the boat right at the house for easy access for sunset boat rides and our everyday fishing adventures. "
United States
Ashley C.
Islamorada Boaters Paradise with 70' Dock and private beach access..

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Matecumbe
10.0 out of 10, Exceptional, (106)
"We had the best time relaxing in paradise at this magnificent home!"
United States
Sarah A.
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Venetian Shores
9.6 out of 10, Exceptional, (58)
"Second stay in 3 years. Highly recommend!"
United States
Don B.
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Final open week of 2026 - Dec 13th - 20th Stunning Oceanfront Estate

Matecumbe
10.0 out of 10, Exceptional, (57)
"This was a wonderful home to gather in! It was clean, big enough for 3 families, the pool was clean, they even has paddle boards, bikes and kayaks you could use. You could fish off the dock, which our 5 year old couldn’t get enough of, fully stocked kitchen with any utensil and pan you would ever need. Really great place to stay. Oh, and the host was superb, and question we had she answered in minutes! "
United States
Debra H.
Final open week of 2026 - Dec 13th - 20th Stunning Oceanfront Estate

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Islamorada
10.0 out of 10, Exceptional, (185)
"Overall a good trip. A few items needed to be taken care of, but it didn't stop us from having a great time."
United States
Darrell P.
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Private Beachfront Paradise

Matecumbe
9.6 out of 10, Exceptional, (76)
"We enjoyed our stay. We would probably stay again."
United States
William I.
Private Beachfront Paradise

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

Islamorada
10.0 out of 10, Exceptional, (114)
"House was as described with great access to pool and dock"
United States
Matt Y.
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Islamorada Hotel Reviews

Find out more about Islamorada

Everything you need to know about Islamorada holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Islamorada holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Islamorada holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Islamorada holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Islamorada. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islamorada holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Islamorada holiday rentals we have selected for you start as low as €111 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Islamorada rentals

At Expedia, we put the best Islamorada holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Islamorada rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Islamorada holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Islamorada. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This highly rated holiday home rental in Islamorada offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Some other homes for rent in Islamorada include Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7 and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many holiday rentals are there in Islamorada?

With 491 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Founders Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

What’s a holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.