Islamorada Holiday Rentals

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Holiday Rentals in Islamorada

Treasure Harbor

3.0 star property
Islamorada
9.0 out of 10, Wonderful, (109)
"Unique House boat experience, friendly staff. "
United States
Luis
Treasure Harbor

Breezy Palms Resort

2.5 star property
Matecumbe
8.8 out of 10, Excellent, (565)
"Best hotel for the price"
United States
luzdari
The price is NZ$216
includes taxes & fees
16 Nov - 17 Nov
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (68)
"Beautiful property!"
United States
Betty
The price is NZ$1,253
includes taxes & fees
17 Nov - 18 Nov
The Islands of 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 traveller
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

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

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

Matecumbe
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..

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

Islamorada
9.8 out of 10, Exceptional, (34)
"Very private. Exactly like photos."
United States
jane b.
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen

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

Matecumbe
10.0 out of 10, Exceptional, (86)
"House was perfect for our family vacation."
United States
Jackie G.
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

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

Islamorada
9.8 out of 10, Exceptional, (153)
"Great place! Exactly as described."
United States
Angela K.
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

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

Matecumbe
9.6 out of 10, Exceptional, (86)
"Our stay was great, close to everything! Loved the Manitees that came right into the harbor! The house was very clean and just the right size for 4."
United States
Lorraine C.
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

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

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

Matecumbe
10.0 out of 10, Exceptional, (106)
"The property was a perfect fit for our three family spring break. Plenty of ways to relax and enjoy the property and great location to all that Islamorada and the surrounding area has to offer. Super friendly and attentive hosts, a well appointed property and a view that we’ll never forget. "
United States
Chip W.
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Matecumbe
10.0 out of 10, Exceptional, (120)
"Wonderful location."
United States
Keith M.
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

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

Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock

Islamorada
Anglers Reef Islamorada Oceanfront 3BR Pool Front Home Private Beach & Boat Dock

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

Matecumbe
9.2 out of 10, Wonderful, (16)
"Overall the property was nice. Very quaint. A previous review mentioned how small the bathroom was. I agree, but for us it wasn't a huge ordeal. I would say it made it challenging when trying to get ready because the sink takes up all the counter space. Luckily there is a wall shelf in the kitchen that we utilized. Would be nice to have mirrors in the bedrooms, and maybe some shelving in the bathroom to set items on during the stay. Our front door seemed to lack the shades that the other...
United States
Tracie C.
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

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!

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

Matecumbe
10.0 out of 10, Exceptional, (1)
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
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 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 NZ$216 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?

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 Islamorada Boaters Paradise with 70' Dock and private beach access.. and Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip. .

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 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 Bud n' Mary's Dive Center and Anne's Beach.

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.