Islamorada Holiday Rentals

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Holiday Rentals in Islamorada

Our top choices for Islamorada holiday rentals

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (102)
"Unique House boat experience, friendly staff. "
The price is AU$369
includes taxes & fees
8 Sept - 9 Sept
Treasure Harbor

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (526)
"Best kept secret, love staying here,!"
The price is AU$195
includes taxes & fees
7 Sept - 8 Sept
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 AU$1,028
includes taxes & fees
7 Sept - 8 Sept
The Islands of Islamorada

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

10.0 out of 10, Exceptional, (84)
"Enjoyed greatly!Fantastic host!!"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

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

9.6 out of 10, Exceptional, (32)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

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

10.0 out of 10, Exceptional, (195)
"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

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

10.0 out of 10, Exceptional, (58)
"This home has everything for you to have Fun in Islamorada. Close to everything!"
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

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

10.0 out of 10, Exceptional, (185)
"Lodgings first rate. Boat access to Mahi and Grouper catches."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

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.

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

10.0 out of 10, Exceptional, (105)
"We loved everything about this house! The outdoor areas were perfect. We had everything we needed to have a great time at the house but close enough to venture out and explore the keys if we wanted. Owners were responsive and great to work with"
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

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

9.6 out of 10, Exceptional, (83)
"Great"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes

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

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

Oceanfront-Spacious 4 BR home, NEW Kitchen, Pool & Beach, 31' Boat Slip INCLUDED

9.8 out of 10, Exceptional, (33)
"Everything was wonderful. House was great with beautiful water views!!!"
Oceanfront-Spacious 4 BR home, NEW Kitchen, Pool & Beach, 31' Boat Slip INCLUDED

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

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 Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

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

10.0 out of 10, Exceptional, (23)
"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..

Islamorada retreat "Bungalow Blue" w/ heated pool, Bikes, BBQ, amenities galore!

10.0 out of 10, Exceptional, (18)
"Great Stay!"
Islamorada retreat "Bungalow Blue" w/ heated pool, Bikes, BBQ, amenities galore!

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

9.8 out of 10, Exceptional, (93)
"This property was perfect for our Spring Break vacation! Plenty of space, clean, great area, nice pool and beach!"
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

10.0 out of 10, Exceptional, (90)
"This was a wonderful place to call home while visiting the beautiful Florida Keys. It was beautifully decorated, comfortable and filled with everything you could possibly need to make your vacation great. We would definitely stay here again! Highly recommended to any travelers. Wonderful host and excellent communication throughout our stay.Thank you!!!"
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
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

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$195 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?

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7: This highly rated holiday home rental in Islamorada is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a rooftop terrace, a private garden and a selection of games so that you can immerse yourself in your holiday. Some other homes for rent in Islamorada include Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada and OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars.

How many holiday rentals are there in Islamorada?

With 499 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.