Islamorada Vacation Rentals

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Vacation Rentals in Islamorada

Property grounds
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
10.0 out of 10, Exceptional, (1)
"Very hood stay"
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
Pool
Southern Diversion Estate Islamorada see our winter discounts
10.0 out of 10, Exceptional, (62)
"We had a wonderful family stay. Jon, the property manager was very helpful during check in! We loved the location, so close to grocery shopping and restaurants. We spent a lot of our time at the house , enjoying the gorgeous outdoor areas. The water was beautiful! We were six adults and six younger children. It was really nice to have so much room for everyone! The beds and linens were very comfortable, always important to us! We had a great time and will be visiting again!"
Southern Diversion Estate Islamorada see our winter discounts
On the beach, sun loungers, beach towels
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
10.0 out of 10, Exceptional, (64)
"Loved the property and had a great time but the luxury in the listing was not there. The biggest issue being the pergola in the pictures was gone and replaced with a single umbrella. The string lights in the backyard were broken and the majority of items were powered by extension cords laying on the ground, many with tripped breakers. The pool/hot tub was unable to be controlled and we needed to text someone whenever we wanted a change. The outdoor cinema experience was a projector in a box that...
Sensational Ocean Front Villa | Kayak+PBs+Cinema+Fire Pit+Pool
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Pool
Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!
10.0 out of 10, Exceptional, (6)
"Perfect for a getaway weekend in paradise"
Penthouse Paradise | Developer Unit w/ Every ★ Upgrade Possible!!
Outdoor pool, a heated pool
Oceanfront, Spacious Gourmet Kitchen, Includes 31' Boat Slip, Dock, Pool & Beach
10.0 out of 10, Exceptional, (18)
"Exceeded all expectations"
Oceanfront, Spacious Gourmet Kitchen, Includes 31' Boat Slip, Dock, Pool & Beach
Pool | Outdoor pool, a heated pool
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
10.0 out of 10, Exceptional, (75)
"Property was beautiful and bungalow super comfy and clean. We decided last minute to drive down to Islamorada with our 2 small dogs for our anniversary, and Miranda made everything flow so smoothly, I could not ask for more. Thank you for sharing your lovely home with us. Everything was absolutely perfect."
Tiki Bar,Heated Pool,Pri Spa, kayaks,SUP’s,Bikes,BBQ,Fire ring, outside TV, more
Exterior
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
10.0 out of 10, Exceptional, (8)
"Beautiful, spotlessly clean, comfortable, well appointed, great pool! A lovely little cottage that had everything we needed! Perfect stay!"
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
On the beach
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
10.0 out of 10, Exceptional, (96)
"My family and I had a wonderful week at Angler's Reef. The house was absolutely beautiful, clean and very well kept. The kitchen was fully stocked which was great as we cooked several meals while visiting. The pool and grounds are well maintained, and the community has a safe, friendly vibe. We would highly recommend this home and Angler's Reef."
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
Outdoor pool, a heated pool
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
10.0 out of 10, Exceptional, (107)
"Great location and property. Would love to stay again in the future."
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
Beach nearby, sun loungers, beach towels
Peacock Shores Islamorada - Vacation On The Beach!
10.0 out of 10, Exceptional, (25)
"Such a serene location and beautiful well appointed home. We loved everything about it!"
Peacock Shores Islamorada - Vacation On The Beach!
Pool | Outdoor pool, a heated pool
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
10.0 out of 10, Exceptional, (6)
"Great Property, Awesome Location, Very Reasonably Priced, Super Nice Owner…wish we could have stayed longer. We arrived Friday afternoon after spending the morning in Everglades Safari Parl and stopping by Alabama Jacks for lunch in Key Largo. We unpacked, checked things out (including the pool) before heading over to Robbie’s for an amazing sunset catamaran cruise …checked out the old lighthouse, saw dolphins and the most amazing sunset and beautiful water that I’ve typically only seen in the...
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Aerial view
💎AQUAMARINE💎<-WALL 2 WALL-> OCEAN-VIEW🌊+DOCK+POOL+SPA+GYM+🎾+DEALS ⭐️⭐️⭐️⭐️⭐️
10.0 out of 10, Exceptional, (134)
"This property was the start of our 2 week break in Florida, what a fantastic place to stay. Great position to wake up to the sunrise and then take the boat out later in the day to see the sunset. Communication throughout was excellent and it seemed as if we had the place to ourselves, the community areas were very quiet."
💎AQUAMARINE💎<-WALL 2 WALL-> OCEAN-VIEW🌊+DOCK+POOL+SPA+GYM+🎾+DEALS ⭐️⭐️⭐️⭐️⭐️
Beach | On the beach, beach towels
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
9.8 out of 10, Exceptional, (13)
"Me and 2 buddies stayed here while we went fishing. The place is a good place to stay with friends or family. 3 bedrooms and close to the pool and beach."
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
A heated pool
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
9.8 out of 10, Exceptional, (140)
"We really enjoyed our time at this villa! Owners were super accommodating and loved the location!"
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
Property grounds
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
9.6 out of 10, Exceptional, (71)
"The Irvine’s are great hosts, and we had a wonderful week. This house is a great location for boaters, with easy access to both the gulf and Atlantic. We will look forward to another stay."
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers
The Islands of Islamorada
4.0 star property
9.6 out of 10, Exceptional, (35)
"My wife and I have been traveling to Islandmorada for many years and this place is what we have been searching for. Clean, quaint, all the amenities of a large restort withiut the corporation feel. Absolutely refreshing!"
The Islands of Islamorada
Pool | Outdoor pool
Private Beachfront Paradise
9.6 out of 10, Exceptional, (60)
"Beautiful property, incredibly private. The beach, deck, and outside areas were spectacular. We had three chicken friends that visited every day! We traveled to Marathon, Key West, and Tavernier while there, as well as Islamorada. Publix was right in town and we bought some groceries there, but also enjoyed many area restaurants. I think the listing should be updated as the beds were configured differently than we thought (2 bedrooms had 2 twin beds) and it worked for our family but might not...
Private Beachfront Paradise
Pool
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
9.6 out of 10, Exceptional, (15)
"Location , staff , general area, cleanliness all were excellent. Loved our condo."
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
On the beach
Relaxing waterfront retreat with boat dock & amazing ocean views
9.4 out of 10, Exceptional, (3)
"house needs updating"
Relaxing waterfront retreat with boat dock & amazing ocean views
Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very Good, (316)
"A relaxing vibe. Very enjoyable stay"
The price is $144
$214 total
includes taxes & fees
May 16 - May 17
Breezy Palms Resort
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See all available properties in Islamorada
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.

Islamorada Vacation Rental Travel Info

Number of vacation rentals
55
Popular accommodation
Islamorada private vacation homes
Known landmarks
Theater of the Sea, Anne's Beach and Florida Keys Brewing Co.
International airport
Miami, FL (MIA-Miami Intl.)

Other types of properties in Islamorada you may be interested in

Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
4.0 star property
9.0 out of 10, Wonderful, (1005)
"Beautiful property"
The price is $399
$511 total
includes taxes & fees
Jun 10 - Jun 11
Cheeca Lodge & Spa
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1322)
"This was my first time in the Keys and this hotel did not disappoint. The property is beautiful, staff is super friendly and helpful and the location is perfect if you’re planning on checking out other islands. Islamorada is just under 2 hours from Key West so it’s easily drivable. I would absolutely stay here again. "
The price is $199
$264 total
includes taxes & fees
May 19 - May 20
Chesapeake Beach Resort
Exterior
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1243)
"The resort was absolutely beautiful and the staff go above and beyond. The room key bracelets were so convenient and so cute to wear. We even got to keep them as souvenirs. Definitely the best place I have ever stayed. "
The price is $270
$359 total
includes taxes & fees
May 19 - May 20
Amara Cay Resort
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 low season months. For more hustle and bustle, you may prefer to visit Islamorada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $144 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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.

Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals close to well known points of interest in Islamorada, or you can choose a more remote 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 vacation home rentals that Islamorada has to offer?

Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip: This highly rated vacation home rental in Islamorada is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Islamorada?

With 631 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Everglades National Park and Founders Park are a couple of scenic spots to enjoy the outdoors, whereas History of Diving Museum is one of the cultural attractions. Other places in town to visit include Bud n' Mary's Dive Center and Anne's Beach.

What’s a vacation rental in Islamorada like?

A vacation rental is a private property where you can stay for a couple of days or more in Islamorada. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.

Recent reviews of Islamorada properties
Expedia verified reviews

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

5/5 Excellent
"The property looks simple from the highway, but when you get there, it is gorgeous! The rooms are very spacious and include most amenities you will need. The setting is peaceful and quiet, and mostly beautiful. I’ll stay there again. "
A verified traveler stayed at Fisher Inn Resort & Marina
Posted 2 days ago
Fisher Inn Resort & Marina