Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (112)
"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
$251 nightly
The price is $283
Nov 30 - Dec 1
Total with taxes and fees
Treasure Harbor

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (573)
"Best hotel for the price"
United States
luzdari
$121 nightly
The price is $136
Nov 30 - Dec 1
Total with taxes and fees
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (68)
"Great for family vacation with kids. love it"
United States
Dixania
$749 nightly
The price is $843
Nov 30 - Dec 1
Total with taxes and fees
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

Only 3 weeks left in 2025 for a pre-Christmas getaway! Oceanfront/Pool/dock

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.
Only 3 weeks left in 2025 for a pre-Christmas getaway! Oceanfront/Pool/dock

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

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

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

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

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

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 traveler
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

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

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!

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!

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..

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

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

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.

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Top Islamorada Hotel Reviews

Find out more about Islamorada

Everything you need to know about Islamorada vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Islamorada vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Islamorada vacation 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 low season months. For more hustle and bustle, you may prefer to visit Islamorada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Islamorada rentals

At Expedia, we put the best Islamorada vacation 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 vacation.

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 vacation rental in Islamorada?

Yes, we have vacation rentals close to well known points of interest in Islamorada, or you can choose a more remote 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 vacation home rentals that Islamorada has to offer?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a barbecue grill, 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 Islamorada Boaters Paradise with 70' Dock and private beach access.. and Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker.

How many vacation rentals are there in Islamorada?

With 489 Expedia vacation rentals, you're sure 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 vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.