Islamorada Vacation Rentals

Vacation Rentals in Islamorada

Exterior
Breezy Palms Resort
2.5 star property
8.4 out of 10, Very Good, (328)
"Love it!"
The price is $134
$167 total
includes taxes & fees
30 May - 31 May
Breezy Palms Resort
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
Property grounds
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
10.0 out of 10, Exceptional, (2)
"We stayed for a week in late April. The location couldn't be better, and having a boat dock was amazing. We had lots of pool time and time on the water. The house had everything we needed to make our stay in Islamorada a dream. We'll be back for sure!"
Beautiful Waterfront Villa 133 Anglers Reef with on-site Boat Slip
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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!
Pool
Southern Diversion Estate Islamorada see our winter discounts
10.0 out of 10, Exceptional, (63)
"It was just as advertised"
Southern Diversion Estate Islamorada see our winter discounts
A heated pool
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
9.8 out of 10, Exceptional, (142)
"ANGLER'S REEF house is really good on so many levels. Modern everything, clean and user friendly. Property has great beach and awesome pool. Close to everything you will want to do, eat at or hang out. Host/mgr is easy to reach and communicate with. Let me know if you can't make it and we'll go for you...!"
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
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
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
Terrace/patio
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
8.0 out of 10, Very Good, (7)
"Stressful upon arrival as we had not yet received our access code. It took 40 minutes to finally reach someone at Vacasa’s to assist us. The patio door screens were both off the track leaning against the outdoor wall. 2 kitchen light bulbs were burnt out. The queen mattress had stains in both sides. The bottom of our feet were dirty from walking on the tile floor. Clear lay not cleaned properly patio furniture had oversized cushions that didn’t fit the furniture properly"
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
Aerial view
House in Islamorada, in exclusive Venetian Shores.
House in Islamorada, in exclusive Venetian Shores.
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
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
Property grounds
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Luxurious PH 5BR 3.5BA Gym/ Pool & Jacuzzi/ Sauna
Pool
Penthouse Paradise Developer Unit with Every Upgrade Possible
10.0 out of 10, Exceptional, (6)
"Perfect for a getaway weekend in paradise"
Penthouse Paradise Developer Unit with Every Upgrade Possible
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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, (1002)
"Lovely experience. A place we will come back to visit. "
The price is $319
$426 total
includes taxes & fees
30 May - 31 May
Cheeca Lodge & Spa
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
2.5 star property
9.0 out of 10, Wonderful, (1332)
"We really enjoyed it, staff was very nice and property was nice and clean. It has 2 pools and beach access. We would definitely come back!"
The price is $238
$308 total
includes taxes & fees
30 May - 31 May
Chesapeake Beach Resort
Exterior
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1233)
"Small but very comfortable resort in Islamorada. Great resort activities available and communicative, helpful staff. The wait staff at the restaurant were fantastic. Well priced resort experiences such as snorkeling and professional photography! Shout out to Captain Ken, his wife, and Javier the photographer! "
The price is $288
$380 total
includes taxes & fees
27 Jun - 28 Jun
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 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.

How many vacation rentals are there in Islamorada?

With 629 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National 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 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 亿客行 verified reviews

Pines & Palms Resort

Pines & Palms Resort

5/5 Excellent
"Customer Service and tranquility "
A verified traveler stayed at Pines & Palms Resort
Posted 1 day ago
Pines & Palms Resort