Islamorada Vacation Rentals

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Our top choices for Islamorada vacation rentals

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (682 reviews)
"Amazing stay with my son! Close to everything - right in ocean, beach front and large room! Will stay again for sure!"
United States
Paul
$121 nightly
The price is $136
May 28 - May 29
Total with taxes and fees
Breezy Palms Resort

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.0 out of 10, Wonderful, (2 reviews)
"La propiedad me encantó se las recomiendo 100/100%"
United States
Marta
$203 nightly
The price is $228
May 27 - May 28
Total with taxes and fees
Caloosa Cove Resort by CoolVacay

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (37 reviews)
"Comfortable and well thought out space."
United States
Jessica E.
$369 nightly
The price is $410
May 27 - May 28
Total with taxes and fees
Charming Home in Key Largo

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (115 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$394 nightly
The price is $438
May 27 - May 28
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

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.
$209 nightly
The price is $233
May 27 - May 28
Total with taxes and fees
Flip-Flops & Sunshine: Islamorada Studio Escape

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, (19 reviews)
"Perfect Stay."
United States
suhaela s.
$405 nightly
The price is $450
May 27 - May 28
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (47 reviews)
"There was no staff but the apartment was spotless and very well appointed with amenities like coffee, etc. Everything was clean, neat and new feeling. The beds were very comfortable and the apartment was spacious and welcoming with great views."
United States
Sandra
$394 nightly
The price is $438
May 27 - May 28
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Nauti Hideaway Ocean Pointe 2314

Nauti Hideaway Ocean Pointe 2314
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"Great communication. Very clean. We loved view from the room. We would definitely stay here again!"
United States
Cynthia L.
$409 nightly
The price is $445
Jun 25 - Jun 26
Total with taxes and fees
Nauti Hideaway Ocean Pointe 2314

Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (48 reviews)
"Exceeded expectations, exceptionally clean, great for kids (they loved the pool), perfect for our Keys trip"
United States
Natalie M.
$349 nightly
The price is $388
Jun 1 - Jun 2
Total with taxes and fees
Amazing Ocean view condo

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.
$209 nightly
The price is $233
May 27 - May 28
Total with taxes and fees
Coastal Studio Getaway – Second Floor with Partial Water Views

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Tavernier
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful condo with nice decor. We enjoyed the pool and was nice having a restaurant on site. I would definitely stay there again "
United States
Cathy
$402 nightly
The price is $436
Jun 1 - Jun 2
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Tavernier
10.0 out of 10, Exceptional, (8 reviews)
"Great location and clean"
United States
Matthew H.
$451 nightly
The price is $491
Jun 15 - Jun 16
Total with taxes and fees
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Tavernier
9.0 out of 10, Wonderful, (97 reviews)
"Right in the heart of Key Largo but just off the beaten path. Clean, comfortable and cozy. The property has a beach, pool and restaurant which was convenient after a long day of travel."
United States
jodi
$299 nightly
The price is $332
May 27 - May 28
Total with taxes and fees
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Tavernier
$263 nightly
The price is $292
Jun 7 - Jun 8
Total with taxes and fees
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

Blue Haven Key Largo | Ocean Pointe 1315

Blue Haven Key Largo | Ocean Pointe 1315
Tavernier
9.8 out of 10, Exceptional, (16 reviews)
"The unit was clean. The bed was comfortable. Everything worked well."
United States
William G.
$418 nightly
The price is $455
Jun 17 - Jun 18
Total with taxes and fees
Blue Haven Key Largo | Ocean Pointe 1315

OP-2 Ocean View w/heated pool beach marina

OP-2 Ocean View w/heated pool beach marina
Tavernier
8.4 out of 10, Very Good, (11 reviews)
"Great location, thoughtful set-up. "
United States
Michelle J.
$304 nightly
The price is $337
Jun 15 - Jun 16
Total with taxes and fees
OP-2 Ocean View w/heated pool beach marina

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, (2 reviews)
"The unit was exactly as listed. Very clean. Located in a great area."
United States
Seth M.
$205 nightly
The price is $227
May 31 - Jun 1
Total with taxes and fees
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Very nice small resort."
United States
Dan
$270 nightly
The price is $304
Jun 9 - Jun 10
Total with taxes and fees
Island Bay Resort

Toes in the Sand - 2 Bedroom Condo Sleeps 4

Toes in the Sand - 2 Bedroom Condo Sleeps 4
Tavernier
10.0 out of 10, Exceptional, (39 reviews)
"Very clean and nice amenities"
United States
Shelley R.
$351 nightly
The price is $390
May 28 - May 29
Total with taxes and fees
Toes in the Sand - 2 Bedroom Condo Sleeps 4

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (167 reviews)
"Condo was beautiful would definitely stay here again."
United States
Dan M.
$404 nightly
The price is $448
May 31 - Jun 1
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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 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 $136 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 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?

Next available - August 2026 - Oceanfront - Heated Pool - Dock: This Islamorada vacation home rental 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 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a rooftop terrace, a private yard, and a selection of games so you can immerse yourself in your vacation. Some other homes for rent in Islamorada include Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada and Anglers Reef Islamorada home with ocean views, private marina, beach & pool.

How many vacation rentals are there in Islamorada?

With 409 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.