Islamorada Holiday Rentals

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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. "
United States
JoAnn
The price is AU$388
includes taxes & fees
28 Oct - 29 Oct
Treasure Harbor
Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (550)
"Nice place to stay for the wedding I went to "
United States
michael
The price is AU$188
includes taxes & fees
3 Nov - 4 Nov
Breezy Palms Resort
The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (67)
"Great for family vacation with kids. love it"
United States
Dixania
The price is AU$1,038
includes taxes & fees
23 Oct - 24 Oct
The Islands of Islamorada
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. "
United States
Kimber T.
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
10.0 out of 10, Exceptional, (198)
"We had a fantastic stay at this property it was the perfect choice for our family vacation. Located in a secure gated community, the home is centrally situated near all the attractions and activities in Islamorada. The house itself is beautifully maintained, and the pool was a highlight for everyone. Craig, the owner, was incredibly helpful and welcoming, making the entire experience even better. We’re already looking forward to booking this home again for our next trip!"
United States
Nikki G.
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
BeachFront Paradise/By The Glam Homes
BeachFront Paradise/By The Glam Homes
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
10.0 out of 10, Exceptional, (105)
"Chauncey was awesome and very accommodating."
United States
Craig R.
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
10.0 out of 10, Exceptional, (118)
"Wonderful location."
United States
Keith M.
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
9.6 out of 10, Exceptional, (32)
"Nice property . Well kept. Good management "
United States
jose
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
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! "
United States
Nicole L.
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
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!
Studio Escape at Caloosa Cove, Islamorada
10.0 out of 10, Exceptional, (2)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
Studio Escape at Caloosa Cove, Islamorada
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."
United States
Chris S.
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Topsider Resort
3.5 star property
8.8 out of 10, Excellent, (62)
"Its a great choice for small families looking to relax. Heated pool and hot tub. on property beach access (gulf side). Kayaks and bikes to use. inside the dwelling, master bedroom w/ full bath, another bedroom w/ two twin beds, another full bath, full kitchen + kitchenette, and living room. Really pleased. "
United States
Thomas J.
Topsider Resort
Beautiful two- story beach house
Beautiful two- story beach house
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!"
United States
Jennifer S.
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 "
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!
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!
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen
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
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. "
United States
Susan H.
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, 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 favourite 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 depend 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 AU$188 per night. Entering your travel dates in the search wizard might find you 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?

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars: This highly rated holiday home rental in Islamorada is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Islamorada include BeachFront Paradise/By The Glam Homes and Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7.

How many holiday rentals are there in Islamorada?

With 488 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.