Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

2.5 out of 5
84801 Overseas Highway, Islamorada, FL
The price is $159 per night from Nov 28 to Nov 28
This family-friendly Islamorada aparthotel is located on the Strip, within 2 mi (3 km) of Windley Key Fossil Reef Geological State Park and History of Diving ...
3.3/5 (347 reviews)
"The pool was open 24 hours a day nice setting nice area"

Reviewed on Nov 13, 2021

Coconut Cove Resort and Marina
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Nestled on the beach, this Islamorada villa is within 2 mi (3 km) of History of Diving Museum, Florida Keys Brewing Co., and Hurricane Monument. Bud n' Mary's ...
4.5/5 Wonderful! (11 reviews)
"Absolutely loved the atmosphere. Our suite was amazing. Everything was clean and well maintained. Everyone was so nice and helpful."

Reviewed on Nov 18, 2021

The Islands of Islamorada
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway, Islamorada, FL
The price is $99 per night from Dec 1 to Dec 1
Nestled on the beach, this Islamorada aparthotel is within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park. Hurricane Monument ...
4/5 Very Good! (45 reviews)
getaway
"Cute place, convenient to a lot of restaurants. Right on the water and very quiet. definitely would stay there again."

Reviewed on May 29, 2021

Breezy Palms Resort
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Topsider Resort by Capital Vacations

Topsider Resort by Capital Vacations

3.5 out of 5
75500 Overseas Hwy, Islamorada, FL
Nestled on the beach, this Islamorada condo building is within 1 mi (2 km) of Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. ...
4.4/5 Excellent! (47 reviews)
Topsider was a great little resort
"The Topsider was a great little resort - 20 raised 2 BR octagonal-shaped cottages on the property. Our cottage was clean, eqipped with all the kitchen utensils dishes linens we needed. The furniture was in good condition, but the washing machine didnt work. The beach and dock were fine, there were ..."

Reviewed on Aug 15, 2021

Topsider Resort by Capital Vacations
Angler's Reef Resort by KeysCaribbean

Angler's Reef Resort by KeysCaribbean

3.5 out of 5
84977 Overseas Highway, MM 84.9, Islamorada, FL
Nestled on the beach, this Islamorada vacation home is within 3 mi (5 km) of Windley Key Fossil Reef Geological State Park, Founders Park, and History of Diving ...
4.7/5 Exceptional! (12 reviews)
"The pool and the beach are incredible. Great place to stay. Great family vacation spot."

Reviewed on Mar 14, 2021

Angler's Reef Resort by KeysCaribbean
Islamorada Escape - Bungalow #1 - Cozy, clean, tropical oasis!

Islamorada Escape - Bungalow #1 - Cozy, clean, tropical oasis!

Islamorada, FL
Situated by the sea, this romantic vacation home is 0.4 mi (0.7 km) from San Pedro Underwater Archaeological Preserve State Park and within 3 mi (5 km) of Indian ...
5/5 Exceptional! (35 reviews)
We enjoyed our stay and would recommend it to our friends.
"Caitlin was great to work with. The bungalow was cute and perfect for 2 people wanting to relax."

Reviewed on Nov 16, 2021

Islamorada Escape - Bungalow #1 - Cozy, clean, tropical oasis!
Penthouse Views - Futura Yacht Club #604

Penthouse Views - Futura Yacht Club #604

Islamorada, FL
Situated in Islamorada, this condo building is 1.3 mi (2.1 km) from Founders Park and within 6 mi (10 km) of Mariners Hospital and Windley Key Fossil Reef Geological ...
4.8/5 Exceptional! (12 reviews)
Nice Property in the Florida Keys
"The property was as advertised, nice unit in the middle of the Florida Keys. Convenient access to great restaurants, grocery stores, pharmacracies etc. We only had a minor issue when the electronic door lock malfunctioned, the manager answered my call immediately and remedied our issue quickly. The ..."

Reviewed on Sep 1, 2021

Penthouse Views - Futura Yacht Club #604
Luxury beachfront home with pool in Islamorada

Luxury beachfront home with pool in Islamorada

Islamorada, FL
Situated on the beach, this vacation home is within 1 mi (2 km) of Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. Anne's Beach ...
Luxury beachfront home with pool in Islamorada
Oceanfront Islamorada Condo with Boat Slip

Oceanfront Islamorada Condo with Boat Slip

Islamorada, FL
Situated by the ocean, this condo building is 1.2 mi (2 km) from Founders Park and within 6 mi (10 km) of Theater of the Sea and Windley Key Fossil Reef Geological ...
5/5 Exceptional! (4 reviews)
Pure heaven
"The view is spectacular. The unit is modern, open, airy, spacious and includes brand new washer/dryer. Views from everywhere. The large screened patio with brand new grill enhances outdoor living. One could not ask for a better community. Convenient pool, pond and marina with very welcoming neighbors ..."

Reviewed on Apr 15, 2021

Oceanfront Islamorada Condo with Boat Slip
Unique Stay Aboard Our Florida Keys Yacht

Unique Stay Aboard Our Florida Keys Yacht

Islamorada, FL
Situated in Islamorada, this houseboat is 0.7 mi (1.2 km) from Florida Keys Brewing Co. and 2.7 mi (4.4 km) from Theater of the Sea. Hurricane Monument and History ...
5/5 Exceptional! (3 reviews)
What a great boat...What a perfect spot!
"Three nights were just enough here dockside in Islamorada. The boat is beautiful and clean, and Andy and his wife were nice and answered any questions quickly. The restaurant/bar is so close- with live music every night we could enjoy from the boat. Great area- not many beaches , but lots of water ..."

Reviewed on Nov 30, 2019

Unique Stay Aboard Our Florida Keys Yacht
 Spring & summer dates available licensed rental vr #131 ( NO BOATS)

Spring & summer dates available licensed rental vr #131 ( NO BOATS)

Islamorada, FL
This family-friendly Islamorada condo building is located on the beach, 1.3 mi (2 km) from Founders Park, and within 6 mi (10 km) of Theater of the Sea and Laura ...
4.9/5 Exceptional! (14 reviews)
Great place!
"Nice gated community, made me feel safer traveling with all girls. Condo was just what we wanted, clean, nice updates and very well stocked. Very happy we chose this place being our first time to the keys, close to all our excursions and then back to the condo for the evening to enjoy the pool and ..."

Reviewed on Aug 15, 2021

Spring & summer dates available licensed rental vr #131 ( NO BOATS)
FALL SALE!! 20% off November at Peacock Shores Oceanfront Islamorada!

FALL SALE!! 20% off November at Peacock Shores Oceanfront Islamorada!

Islamorada, FL
This family-friendly Islamorada vacation home is located on the waterfront, 1.5 mi (2.4 km) from Founders Park, and within 6 mi (10 km) of Theater of the Sea ...
5/5 Exceptional! (5 reviews)
Great stay!
"Great place, very clean with all amenities. Easy to deal with property managers. Thank you from all!"

Reviewed on Oct 17, 2021

FALL SALE!! 20% off November at Peacock Shores Oceanfront Islamorada!
The Caribbean Resort Hemingway House North

The Caribbean Resort Hemingway House North

4 out of 5
117 South Carroll Street, Islamorada, FL
Situated by the ocean, this vacation home is within a 15-minute walk of Florida Keys Brewing Co. and Hurricane Monument. Indian Key Historic State Park and History ...
The Caribbean Resort Hemingway House North
Hidden Gem Islamorada Top Floor 2Bed/2Bath

Hidden Gem Islamorada Top Floor 2Bed/2Bath

Islamorada, FL
Situated by the sea, this apartment building is within 1 mi (2 km) of History of Diving Museum, Florida Keys Brewing Co., and Hurricane Monument. Indian Key ...
4.9/5 Exceptional! (9 reviews)
Great location
"We came down for a fishing trip out of bud and Mary’s. This place was close to everything we needed. Clean and plenty of room for the 4 of us. The split king wasn’t very comfortable is the only draw back."

Reviewed on Nov 21, 2021

Hidden Gem Islamorada Top Floor 2Bed/2Bath
Stunning Oceanfront Villa with Picturesque Views

Stunning Oceanfront Villa with Picturesque Views

Islamorada, FL
This family-friendly Islamorada villa is located on the beach, within 2 mi (3 km) of History of Diving Museum, Hurricane Monument, and Florida Keys Brewing Co.. ...
Stunning Oceanfront Villa with Picturesque Views
Marlin House @ Tarpon Point ~ Luxury Oceanfront 4/4

Marlin House @ Tarpon Point ~ Luxury Oceanfront 4/4

Islamorada, FL
Situated on the beach, this vacation home is 0.4 mi (0.6 km) from Indian Key Historic State Park and within 3 mi (5 km) of San Pedro Underwater Archaeological ...
5/5 Exceptional! (6 reviews)
Paradise
"This place is everything and more than I expected!!! Will definitely be back!!! Dawn Bates"

Reviewed on Nov 5, 2021

Marlin House @ Tarpon Point ~ Luxury Oceanfront 4/4
Immaculate Oceanfront Villa with Resort Amenities

Immaculate Oceanfront Villa with Resort Amenities

Islamorada, FL
Situated on the beach, this villa is within 2 mi (3 km) of History of Diving Museum, Florida Keys Brewing Co., and Hurricane Monument. Windley Key Fossil Reef ...
5/5 Exceptional! (1 review)
2021 Family Vacation
"This was one of the nicest place we have ever stayed at.!! Simply Gorgeous! The Staff was very kind and accommodating!!"

Reviewed on Aug 26, 2021

Immaculate Oceanfront Villa with Resort Amenities
Ocean Breeze. Oceanfront Resort Style Condo in the Florida Keys (Islamorada)

Ocean Breeze. Oceanfront Resort Style Condo in the Florida Keys (Islamorada)

Islamorada, FL
Situated on the waterfront, this condo building is 0.8 mi (1.3 km) from Founders Park and 3 mi (4.8 km) from Windley Key Fossil Reef Geological State Park. Mariners ...
Ocean Breeze. Oceanfront Resort Style Condo in the Florida Keys (Islamorada)
A Good Stay ~ Islamorada Waterfront Residence

A Good Stay ~ Islamorada Waterfront Residence

Islamorada, FL
Situated by the ocean, this condo building is 1.5 mi (2.4 km) from Founders Park and within 6 mi (10 km) of Mariners Hospital and Windley Key Fossil Reef Geological ...
4.6/5 Wonderful! (5 reviews)
A Good Stay
"Great location on the water and beautiful views. The dock was rough getting in and out of boat. The first few days were rough so I elected to move it to marina, but could have kept it there the rest of the week. There were a few little things that we were able to get past. Inside was clean and we ..."

Reviewed on Aug 27, 2021

A Good Stay ~ Islamorada Waterfront Residence
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Islamorada, FL
This family-friendly Islamorada condo building is located on the waterfront, within 1 mi (2 km) of Sunset Drive Beach and Anne's Beach. San Pedro Underwater ...
5/5 Exceptional! (46 reviews)
Excellent Rating - Unit Had Everything We needed
"I would highly recommend this unit. It is beautifully decorated and stocked with everything you need. It is in a beautiful location. We enjoyed the extras = bicycles, fishing poles and beach/pool toys. Thank you."

Reviewed on Nov 23, 2021

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
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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.

Large Group Rentals Islamorada

The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
The Islands of Islamorada
LICENSED MANAGER - 2/2 VILLA - OCEANFRONT BEACH RESORT - W/10 RENTALS AVAILABLE!

LICENSED MANAGER - 2/2 VILLA - OCEANFRONT BEACH RESORT - W/10 RENTALS AVAILABLE!

Key Largo, FL
The price is $375 per night from Dec 23 to Dec 23
LICENSED MANAGER - 2/2 VILLA - OCEANFRONT BEACH RESORT - W/10 RENTALS AVAILABLE!
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.

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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Islamorada vacation rentals range between $99 per night and $375 per night.

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. 

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