Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Islamorada vacation rentals

Exterior

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (699 reviews)
"Enjoyed this place."
United States
Christopher
$151 nightly
The price is $169
Jun 24 - Jun 25
Total with taxes and fees
Breezy Palms Resort
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (158 reviews)
"Amazing stay!"
United States
Amanda
$252 nightly
The price is $284
Jun 21 - Jun 22
Total with taxes and fees
Treasure Harbor
Exterior

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.6 out of 10, Exceptional, (5 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
$201 nightly
The price is $226
Jun 24 - Jun 25
Total with taxes and fees
Caloosa Cove Resort by CoolVacay
Beach nearby

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Everything was wonderful! We enjoyed our stay very much. "
United States
Colleen D.
$394 nightly
The price is $438
Jun 22 - Jun 23
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Exterior

Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (32 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
$297 nightly
The price is $329
Jul 7 - Jul 8
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Shower, hair dryer, towels, soap

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
$368 nightly
The price is $409
Jun 22 - Jun 23
Total with taxes and fees
Charming Home in Key Largo
Shower, hair dryer, towels, soap

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
10.0 out of 10, Exceptional, (4 reviews)
"Very clean with everything you could need for your time in the Florida keys! The host was very responsive and helpful. Perfect place for a weekend with our dog."
United States
Anonymous traveler
$209 nightly
The price is $233
Jun 22 - Jun 23
Total with taxes and fees
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Pool

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (50 reviews)
"Unit was really nice. The only complaint was the pillows were the worst we have ever used anywhere. We did find a pillow in the closet that was a little less lumpy but very stained. The pool does get very crowded. The beach area is really cute but smelled pretty bad. Overall a great place!"
United States
joleen s.
$338 nightly
The price is $375
Jun 29 - Jun 30
Total with taxes and fees
Amazing Ocean view condo
Private beach, sun loungers, beach umbrellas, beach towels

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (172 reviews)
"Very nice small resort."
United States
Dan
$308 nightly
The price is $347
Jun 21 - Jun 22
Total with taxes and fees
Island Bay Resort
Dining

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Host was very responsive, location safe and wuiet."
United States
Tracey C.
$696 nightly
The price is $773
Jun 23 - Jun 24
Total with taxes and fees
Sunrise Escape - Ocean Front Villa - Sleeps 10
Pool

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
$219 nightly
The price is $244
Jun 25 - Jun 26
Total with taxes and fees
Flip-Flops & Sunshine: Islamorada Studio Escape
Beach

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (168 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
$384 nightly
The price is $427
Jun 22 - Jun 23
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Shower, hair dryer, towels, soap

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo

Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Tavernier
9.6 out of 10, Exceptional, (5 reviews)
"Host was very helpful and responsive! This was our first VRBO stay so we had more questions than seasoned guests, and he was very patient and helpful. Place was as advertised. Bed/pillows were very comfortable. AC was excellent. "
United States
Denise H.
$329 nightly
The price is $366
Jun 22 - Jun 23
Total with taxes and fees
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Exterior

Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views
Matecumbe
9.6 out of 10, Exceptional, (7 reviews)
"laid back and comfortable. "
United States
Joe M.
$219 nightly
The price is $244
Jun 22 - Jun 23
Total with taxes and fees
Coastal Studio Getaway – Second Floor with Partial Water Views
Sun loungers, beach towels

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Tavernier
10.0 out of 10, Exceptional, (21 reviews)
"Cute place! Plenty of room for our family with beautiful view from the balcony. The pool and beach were perfect. We’d stay again! "
United States
Erin G.
$410 nightly
The price is $455
Jul 2 - Jul 3
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Beach nearby

Ocean View Overlooking Marina Ocean Pointe 5305

Ocean View Overlooking Marina Ocean Pointe 5305
Tavernier
10.0 out of 10, Exceptional, (27 reviews)
"Great place with a wonderful view. It has everything you need in the kitchen. We would definitely stay there again. "
United States
Edwina S.
$439 nightly
The price is $478
Jun 21 - Jun 22
Total with taxes and fees
Ocean View Overlooking Marina Ocean Pointe 5305
Beach nearby

Captains Quarters Ocean Pointe 4405

Captains Quarters Ocean Pointe 4405
Tavernier
10.0 out of 10, Exceptional, (14 reviews)
"We had a very pleasant weekend away with all the comforts of home, yet even better with the amazing view! Great communication with the host with quick pleasant responses. The property is conveniently located and easy to get around. "
United States
Debbie W.
$443 nightly
The price is $482
Jun 21 - Jun 22
Total with taxes and fees
Captains Quarters Ocean Pointe 4405
Terrace/patio

Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
10.0 out of 10, Exceptional, (39 reviews)
"Beautifully decorated room with wonderful amenities. We appreciated the full kitchen, comfy beds and early morning ocean views. Kids loved the pool! "
Canada
Alicia
$407 nightly
The price is $451
Jun 23 - Jun 24
Total with taxes and fees
Serene Oceanfront Keys Condo
Beach nearby

Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (133 reviews)
"There’s plenty to do for families of all ages at Ocean Pointe, and the condo was an extremely comfortable place to do it from. The hosts made us feel welcome, and we appreciated their care. "
United States
Sherry G.
$413 nightly
The price is $449
Jun 22 - Jun 23
Total with taxes and fees
Modern and Coastal Ocean Pointe 2307
Miscellaneous

Cozy Waterfront Apartment in Key Largo!

Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (12 reviews)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
$305 nightly
The price is $339
Jun 22 - Jun 23
Total with taxes and fees
Cozy Waterfront Apartment in Key Largo!
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Clean rooms , beautiful view , great breakfast"
Amy 4-night trip
Posted 3 hours ago
Chesapeake Beach Resort

Find out more about Islamorada

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 $169 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Islamorada?

Yes, we have vacation rentals in Islamorada close to MoradaWay Arts & Cultural District, or you can select a secluded option if you want 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?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Some other homes for rent in Islamorada include Private Beachfront Paradise and Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views.

How many vacation rentals are there in Islamorada?

With 415 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 Robbie’s of Islamorada.

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.