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 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (723 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
$138 nightly
The price is $155
Aug 10 - Aug 11
Total with taxes and fees
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
$244 nightly
The price is $275
Aug 11 - Aug 12
Total with taxes and fees
Treasure Harbor
Exterior

3. 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
$281 nightly
The price is $312
Aug 30 - Aug 31
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Interior

4. 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
$264 nightly
The price is $293
Aug 9 - Aug 10
Total with taxes and fees
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Pool

5. 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.
$310 nightly
The price is $344
Aug 9 - Aug 10
Total with taxes and fees
Amazing Ocean view condo
Microwave, stovetop

6. 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.
$333 nightly
The price is $370
Aug 10 - Aug 11
Total with taxes and fees
Private 2-bedroom apartment with kitchen in lovely Tavernier, Key Largo
Private beach, sun loungers, beach umbrellas, beach towels

7. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
$253 nightly
The price is $285
Aug 16 - Aug 17
Total with taxes and fees
Island Bay Resort
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.
$394 nightly
The price is $438
Aug 9 - Aug 10
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Smart TV

9. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (39 reviews)
"Very clean and nice location."
United States
Melinda V.
$335 nightly
The price is $372
Aug 11 - Aug 12
Total with taxes and fees
Charming Home in Key Largo
Beach

10. 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.
$400 nightly
The price is $444
Aug 23 - Aug 24
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Property grounds

11. 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.
$403 nightly
The price is $448
Aug 9 - Aug 10
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Beach nearby

12. Lazy Daze Double King Suite Ocean Pointe 2310

Lazy Daze Double King Suite Ocean Pointe 2310
Tavernier
9.8 out of 10, Exceptional, (36 reviews)
"Loved the beach and pool."
United States
Haley P.
$410 nightly
The price is $445
Sep 8 - Sep 9
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
Pool

13. Family-Friendly 1BR w/ Partial Ocean View & Pool

Family-Friendly 1BR w/ Partial Ocean View & Pool
Tavernier
$311 nightly
The price is $345
Aug 12 - Aug 13
Total with taxes and fees
Family-Friendly 1BR w/ Partial Ocean View & Pool
Marina

14. Island Sanctuary Islamorada

Island Sanctuary Islamorada
Tavernier
9.4 out of 10, Exceptional, (26 reviews)
"We had a great experience. Loved watching the sunset from the top deck. Great to cruise around in the electric catamaran. Kelly’s recommendations were great. We found the sand bar and the Dive restaurant at Mangrove Marina was fun with the live music."
United States
Carrie S.
$379 nightly
The price is $420
Aug 9 - Aug 10
Total with taxes and fees
Island Sanctuary Islamorada
Sun loungers, beach towels

15. 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
9.8 out of 10, Exceptional, (25 reviews)
"The property was in a great location, close to several beach bars and restaurants, the condo was so cute and the host was accessible throughout the entire process before and after our stay."
United States
Alicia
$433 nightly
The price is $481
Aug 17 - Aug 18
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A heated pool

16. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (45 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
$353 nightly
The price is $392
Aug 27 - Aug 28
Total with taxes and fees
Ocean view condo with balcony/marina view
A heated pool

17. 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, (102 reviews)
"Great visit!"
United States
Leigh D. H.
$294 nightly
The price is $327
Sep 8 - Sep 9
Total with taxes and fees
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Marina

18. 1BR Suite w/ Partial Ocean View & Beach Access

1BR Suite w/ Partial Ocean View & Beach Access
Key Largo
$186 nightly
The price is $207
Aug 31 - Sep 1
Total with taxes and fees
1BR Suite w/ Partial Ocean View & Beach Access
Exterior

19. 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.
$386 nightly
The price is $419
Sep 7 - Sep 8
Total with taxes and fees
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
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

8/10 Good
"The ocean view suite had a spectacular view of the basin and ocean. The location is in the middle of everything. The grounds have many private spots right on the ocean. The on site Tiki bar was enjoyable and on Sat there was a live entertainer who was very good. The pools were nice but would be better if cooled. They are remodeling and it was very loud when we arrived on Fri. The associate at the front desk, Jasmine, was professional, responsive, and friendly. She investigated and texted us to let us know it would stop by 5p and not continue until Monday. The room didn't have towel rods or hooks and no wall art. Felt recently remodeled without final touches. These are the only reasons I didn't give it a 5. I would go back."
Theron 1-night trip
Posted 17 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 $155 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?

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks : This Islamorada vacation home rental is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Islamorada include Private Beachfront Paradise and Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 413 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Islamorada County 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.