Holiday Rentals in Islamorada

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Holiday Rentals in Islamorada

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (108)
"If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. "
The price is €217
includes taxes & fees
15 Oct - 16 Oct
Treasure Harbor

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (543)
"Spacious rooms and location was great for what we needed. "
The price is €113
includes taxes & fees
13 Oct - 14 Oct
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is €580
includes taxes & fees
13 Oct - 14 Oct
The Islands of Islamorada

BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes

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

10.0 out of 10, Exceptional, (85)
"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. "
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

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

10.0 out of 10, Exceptional, (105)
"Chauncey was awesome and very accommodating."
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

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

9.6 out of 10, Exceptional, (58)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.

10.0 out of 10, Exceptional, (68)
"Ted’s Place was a 10! Mark and Theresa were wonderful! Easy to communicate with and made sure that the home had everything one might need. Our family absolutely loved the outdoor space and the location in Islamorada couldn’t be better! "
Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.

Beautiful two- story beach house

Beautiful two- story beach house

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (59)
"Fabulous house! Awesome pool, fire pit, dock. My family thoroughly enjoyed every single moment here. Plenty of room for everyone. And the wild life is awesome! Manatees, tropical fish and iguanas!"
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

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

10.0 out of 10, Exceptional, (38)
"Was a nice property and pleasant enough for our stay."
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (118)
"Wonderful location."
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Stunning Oceanfront Estate with Private Pool ~ Beach.

Stunning Oceanfront Estate with Private Pool ~ Beach.

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

9.6 out of 10, Exceptional, (85)
"Great property and great location!"
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

10.0 out of 10, Exceptional, (197)
"We just got back from Islamorada and cannot stop talking about our trip. This property was clean and comfortable and the private development had everything we wanted. Everyone was very nice. I will definitely rent again if/when we return."
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

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

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

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

10.0 out of 10, Exceptional, (185)
"We had a very nice stay at Windley Cottage. Roger & Linda were very nice to work with. They responded quickly to all of our questions prior to our trip and checked in with us during our stay to make sure we had everything we needed. "
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL

10.0 out of 10, Exceptional, (115)
"great location with ocean views, very spacious and comfortably furnished and the amenities like pool and paddle boards/kayaks add to the enjoyment! Boat slip is a huge plus, and hosts have thought of everything, highly recommend!"
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL

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

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

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

10.0 out of 10, Exceptional, (24)
"We loved this house. It had plenty of space for all 8 of us. We enjoyed fishing off the dock, the pool and the private beach. "
Islamorada Boaters Paradise with 70' Dock and private beach access..
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 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 €113 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?

BeachFront Paradise/By The Glam Homes: This highly rated holiday home rental in Islamorada offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. Some other homes for rent in Islamorada include Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock and Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker.

How many holiday rentals are there in Islamorada?

With 489 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 Islamorada County Park and Anne's Beach, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Bud n' Mary's Dive Center and Fiesta Key.

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.