Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

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, (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
Breezy Palms Resort
Exterior

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
The price is CA $269
CA $349 total
includes taxes & fees
May 31 - Jun 1
Caloosa Cove Resort by CoolVacay
Smart TV

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.
The price is CA $199
CA $563 total
includes taxes & fees
May 26 - May 27
Charming Home in Key Largo
Beach nearby

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (114 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
The price is CA $261
CA $612 total
includes taxes & fees
May 26 - May 27
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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.
The price is CA $220
CA $331 total
includes taxes & fees
May 26 - May 27
Flip-Flops & Sunshine: Islamorada Studio Escape
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, (19 reviews)
"Perfect Stay."
United States
suhaela s.
The price is CA $247
CA $629 total
includes taxes & fees
May 26 - May 27
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Property grounds

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
The price is CA $261
CA $612 total
includes taxes & fees
May 26 - May 27
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Beach nearby

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.
The price is CA $256
CA $645 total
includes taxes & fees
Jun 25 - Jun 26
Nauti Hideaway Ocean Pointe 2314
Pool

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.
The price is CA $239
CA $548 total
includes taxes & fees
Jun 1 - Jun 2
Amazing Ocean view condo
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.
The price is CA $220
CA $331 total
includes taxes & fees
May 26 - May 27
Coastal Studio Getaway – Second Floor with Partial Water Views
Beach nearby

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
The price is CA $218
CA $601 total
includes taxes & fees
Jun 1 - Jun 2
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Beach nearby

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.
The price is CA $279
CA $683 total
includes taxes & fees
Jun 15 - Jun 16
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
A heated pool

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
The price is CA $269
CA $466 total
includes taxes & fees
May 26 - May 27
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Beach

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

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Tavernier
The price is CA $183
CA $409 total
includes taxes & fees
Jun 7 - Jun 8
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Beach nearby

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.
The price is CA $249
CA $643 total
includes taxes & fees
Jun 17 - Jun 18
Blue Haven Key Largo | Ocean Pointe 1315
A heated pool

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.
The price is CA $269
CA $466 total
includes taxes & fees
Jun 15 - Jun 16
OP-2 Ocean View w/heated pool beach marina
Interior

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.
The price is CA $138
CA $316 total
includes taxes & fees
May 31 - Jun 1
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
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, (169 reviews)
"Very nice small resort."
United States
Dan
The price is CA $400
CA $450 total
includes taxes & fees
Jun 7 - Jun 8
Island Bay Resort
Terrace/patio

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.
The price is CA $141
CA $547 total
includes taxes & fees
May 28 - May 29
Toes in the Sand - 2 Bedroom Condo Sleeps 4
Beach

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.
The price is CA $269
CA $622 total
includes taxes & fees
May 31 - Jun 1
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

Amara Cay Resort

Amara Cay Resort

8/10 Good
"Un hotel tranquilo con una piscina confortable y vista al mar. No tiene acceso al mar con playa. Las habitaciones son sencillas pero cómodas. Nos facilitaron cuna para bebé. Tiene dos hoteles hermanos de los que uno puede hacer uso."
Daniel 2-night trip
Posted 9 hours ago
Amara Cay Resort

Find out more about Islamorada

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Islamorada. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

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.