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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (741 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
$103 nightly
The price is $115
Sep 8 - Sep 9
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, (173 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$274 nightly
The price is $308
Sep 8 - Sep 9
Total with taxes and fees
Treasure Harbor
Private beach, sun loungers, beach umbrellas, beach towels

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
$227 nightly
The price is $256
Sep 29 - Sep 30
Total with taxes and fees
Island Bay Resort
Exterior

4. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (38 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
$276 nightly
The price is $307
Sep 8 - Sep 9
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Beach nearby

5. 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.
$347 nightly
The price is $386
Sep 8 - Sep 9
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
On the beach, beach towels

6. Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo

Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Tavernier
9.6 out of 10, Exceptional, (233 reviews)
"Our stay was excellent. The home was immaculate and had everything we needed. We would definitely stay here again."
United States
Chris
$332 nightly
The price is $369
Sep 12 - Sep 13
Total with taxes and fees
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Interior

7. 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.
$340 nightly
The price is $379
Sep 8 - Sep 9
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Exterior

8. 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.
$370 nightly
The price is $402
Sep 22 - Sep 23
Total with taxes and fees
Flamingo Flats Ocean Pointe 5306 2BR/2BA
TV

9. Sunrise Sanctuary - Top Floor Ocean Pointe 2415

Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Blain R.
$379 nightly
The price is $412
Sep 29 - Sep 30
Total with taxes and fees
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Smart TV

10. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (40 reviews)
"Very clean and nice location."
United States
Melinda V.
$334 nightly
The price is $370
Sep 8 - Sep 9
Total with taxes and fees
Charming Home in Key Largo
Marina

11. 2BR Oceanfront Suite w/ Beach & Marina Access

2BR Oceanfront Suite w/ Beach & Marina Access
Key Largo
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay. Incredibly clean and homey feel. I felt super safe walking the area after dinner at night"
United States
Alyssa H.
$238 nightly
The price is $264
Sep 14 - Sep 15
Total with taxes and fees
2BR Oceanfront Suite w/ Beach & Marina Access
Beach

12. 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
$381 nightly
The price is $413
Sep 20 - Sep 21
Total with taxes and fees
Aqua Vista Ocean Pointe 3307
Pool

13. 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)
"The space was family friendly and worked well for our stay. The pool area was very clean and the Island Grill on site was great for snacks and drinks while we swam."
United States
Miranda J.
$402 nightly
The price is $437
Sep 29 - Sep 30
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
Pool

14. Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA

Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay! The space had everything we needed and was very comfortable. It is spacious, has an excellent bed and updated finishes. The pool is a great spot to hang out with plenty of chairs. The management team was very helpful and responsive to all of our needs (even on the 4th holiday!). Would definitely stay again."
United States
Chris
$369 nightly
The price is $399
Sep 22 - Sep 23
Total with taxes and fees
Sunrise Penthouse 3316 Ocean Pointe 1BR 2BA
Indoor pool

15. Reel Key Largo Escape Ocean Pointe 5209

Reel Key Largo Escape Ocean Pointe 5209
Tavernier
9.6 out of 10, Exceptional, (10 reviews)
"We had a great time and the property was the center-point of our stay. Thanks for making it easy!"
United States
Ty L.
$371 nightly
The price is $404
Sep 27 - Sep 28
Total with taxes and fees
Reel Key Largo Escape Ocean Pointe 5209
A heated pool

16. 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, (103 reviews)
"Great visit!"
United States
Leigh D. H.
$295 nightly
The price is $328
Sep 8 - Sep 9
Total with taxes and fees
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Beach nearby

17. Ocean View 2BR/2BA Sleeps 6

Ocean View 2BR/2BA Sleeps 6
Tavernier
10.0 out of 10, Exceptional, (136 reviews)
"Very clean and comfortable, wonderful amenities, great view of the ocean, fantastic location and the hosts were so accessible and helpful. We thoroughly enjoyed our stay!"
United States
Deborah D.
$410 nightly
The price is $444
Sep 22 - Sep 23
Total with taxes and fees
Ocean View 2BR/2BA Sleeps 6
A heated pool

18. Ocean Pointe Ocean View w/heated pool beach marina

Ocean Pointe Ocean View w/heated pool beach marina
Tavernier
8.6 out of 10, Excellent, (13 reviews)
"It was really fun and the pizza was good."
United States
Antonio R.
$295 nightly
The price is $328
Sep 9 - Sep 10
Total with taxes and fees
Ocean Pointe Ocean View w/heated pool beach marina
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.
$380 nightly
The price is $414
Sep 29 - Sep 30
Total with taxes and fees
Boho Chic Ocean Pointe 3214 King & Queen
Pool

20. 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.
$402 nightly
The price is $437
Sep 29 - Sep 30
Total with taxes and fees
Lazy Daze Double King Suite Ocean Pointe 2310
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

La Jolla Resort

La Jolla Resort

10/10 Excellent
"Loved this place! driving in I wasn’t too sure but when we open the door to our King suite absolutely stunning clean smelled amazing and walk right up to the water. You can paddleboard kayak. We loved our stay."
Tamara 1-night trip
Posted 2 hours ago
La Jolla 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 $115 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 Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada and Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location! .

How many vacation rentals are there in Islamorada?

With 403 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.