A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Islamorada vacation rentals

Exterior

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (713 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is CA $143
CA $183 total
includes taxes & fees
Aug 2 - Aug 3
Breezy Palms Resort
25-inch flat-screen TV with digital channels, TV

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is CA $175
CA $394 total
includes taxes & fees
Aug 2 - Aug 3
Treasure Harbor
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

3. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is CA $728
CA $897 total
includes taxes & fees
Aug 13 - Aug 14
The Islands of Islamorada
Exterior

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (35 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
The price is CA $137
CA $458 total
includes taxes & fees
Aug 17 - Aug 18
Florida Keys Getaway - Slps 4 - Ocean View
Private beach, sun loungers, beach umbrellas, beach towels

5. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (174 reviews)
"The place is beautiful"
United States
Adriana
The price is CA $359
CA $403 total
includes taxes & fees
Aug 13 - Aug 14
Island Bay Resort
Pool

6. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
The price is CA $195
CA $496 total
includes taxes & fees
Aug 10 - Aug 11
Amazing Ocean view condo
Interior

7. 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 traveller
The price is CA $141
CA $419 total
includes taxes & fees
Aug 10 - Aug 11
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Beach nearby

8. 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.
The price is CA $269
CA $625 total
includes taxes & fees
Aug 4 - Aug 5
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Microwave, stovetop

9. 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.
The price is CA $188
CA $521 total
includes taxes & fees
Aug 2 - Aug 3
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Exterior

10. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great views and very nice condo. The hosts were welcoming and helpful. we truly enjoyed our stay."
United States
Beth H.
The price is CA $211
CA $595 total
includes taxes & fees
Aug 30 - Aug 31
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Exterior

11. 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 $605 total
includes taxes & fees
Aug 30 - Aug 31
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Beach

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is CA $259
CA $612 total
includes taxes & fees
Aug 3 - Aug 4
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Smart TV

13. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is CA $183
CA $554 total
includes taxes & fees
Aug 11 - Aug 12
Charming Home in Key Largo
Beach nearby

14. Marina to Ocean View Key Largo Ocean Pointe 5308

Marina to Ocean View Key Largo Ocean Pointe 5308
Tavernier
9.4 out of 10, Exceptional, (71 reviews)
"The host was quick to respond, condo was perfect, the view was exceptional!"
United States
Rosalie K.
The price is CA $226
CA $616 total
includes taxes & fees
Aug 30 - Aug 31
Marina to Ocean View Key Largo Ocean Pointe 5308
Beach nearby

15. Flamingo Flats Ocean Pointe 5306 2BR/2BA

Flamingo Flats Ocean Pointe 5306 2BR/2BA
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
The price is CA $205
CA $587 total
includes taxes & fees
Aug 30 - Aug 31
Flamingo Flats Ocean Pointe 5306 2BR/2BA
Property grounds

16. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
9.8 out of 10, Exceptional, (48 reviews)
"We were two couples staying in this space with plenty of room. All the amenities on this property (pool, beach restaurant and bar)made this a terrific stay. "
United States
Donna B.
The price is CA $276
CA $634 total
includes taxes & fees
Aug 13 - Aug 14
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Beach

17. Aqua Vista Ocean Pointe 3307

Aqua Vista Ocean Pointe 3307
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
The price is CA $225
CA $613 total
includes taxes & fees
Aug 30 - Aug 31
Aqua Vista Ocean Pointe 3307
Beach

18. 1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries

1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Tavernier
The price is CA $170
CA $433 total
includes taxes & fees
Aug 13 - Aug 14
1BR w/ Pool, Beach, Near Marine & Bird Sanctuaries
Interior

19. Boho Chic Ocean Pointe 3214 King & Queen

Boho Chic Ocean Pointe 3214 King & Queen
Tavernier
9.8 out of 10, Exceptional, (15 reviews)
"The condo was nice and clean. The view from the balcony is very nice. The property is also nice with things to do but not too busy. The host was great and responsive. "
United States
Anthony F.
The price is CA $218
CA $605 total
includes taxes & fees
Aug 30 - Aug 31
Boho Chic Ocean Pointe 3214 King & Queen
Beach nearby

20. Modern and Coastal Ocean Pointe 2307

Modern and Coastal Ocean Pointe 2307
Tavernier
10.0 out of 10, Exceptional, (134 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.
The price is CA $232
CA $623 total
includes taxes & fees
Aug 30 - Aug 31
Modern and Coastal Ocean Pointe 2307
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

10/10 Excellent
"The property was beautiful"
Cindy 5-night trip
Posted 8 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?

Private Beachfront Paradise: This Islamorada vacation home rental is located on the beach and has an outdoor pool, a fireplace, 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Some other homes for rent in Islamorada include Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch and Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views.

How many vacation rentals are there in Islamorada?

With 412 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Founders Park and Anne's Beach 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 Islamorada Brewery & Distillery and Florida Keys Brewing Co..

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.