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 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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, (725 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
$128 nightly
The price is $144
Sep 1 - Sep 2
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, (169 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
$254 nightly
The price is $286
Aug 16 - Aug 17
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)
"Very pleased with our stay"
United States
Vernon Micheal
$253 nightly
The price is $285
Sep 2 - Sep 3
Total with taxes and fees
Island Bay Resort
Marina

4. 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.
$384 nightly
The price is $425
Aug 15 - Aug 16
Total with taxes and fees
Island Sanctuary Islamorada
Marina

5. Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor

Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Tavernier
9.6 out of 10, Exceptional, (33 reviews)
"The apartment was perfect, great location over looking the ocean, and nice and clean. They had everything we needed for our stay, The pool and the hot tub at the resort where clean and welcoming."
United States
Kimberly P.
$457 nightly
The price is $507
Aug 17 - Aug 18
Total with taxes and fees
Ocean Pointe condo ocean view sleeps 6 in Florida keys building 4 top floor
Property grounds

6. 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.
$407 nightly
The price is $452
Aug 16 - Aug 17
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Terrace/patio

7. Serene Oceanfront Keys Condo

Serene Oceanfront Keys Condo
Tavernier
9.8 out of 10, Exceptional, (44 reviews)
"We very much enjoyed our stay! The condo was comfortable and had most everything we needed. We loved the proximity to the pool and the small beach. Property was nice and clean and communicating with the owner was easy. "
United States
Christy W.
$415 nightly
The price is $459
Aug 16 - Aug 17
Total with taxes and fees
Serene Oceanfront Keys Condo
Sun loungers, beach towels

8. 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
$439 nightly
The price is $487
Aug 17 - Aug 18
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
Beach nearby

9. 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.
$399 nightly
The price is $443
Aug 31 - Sep 1
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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.
$405 nightly
The price is $449
Aug 23 - Aug 24
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Beach nearby

11. 3212 Across from Pool * King & Queen/Twin Bunk Bed

3212 Across from Pool * King & Queen/Twin Bunk Bed
Tavernier
9.8 out of 10, Exceptional, (160 reviews)
"Perfect place for family to get away. Plenty of room"
United States
Aaron H.
$428 nightly
The price is $465
Aug 16 - Aug 17
Total with taxes and fees
3212 Across from Pool * King & Queen/Twin Bunk Bed
Exterior

12. 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.
$417 nightly
The price is $452
Aug 16 - Aug 17
Total with taxes and fees
Starfish Seas Ocean Pointe 1302 King/Queen 2BA 2BR
On the beach, beach towels

13. 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, (231 reviews)
"Our stay was excellent. The home was immaculate and had everything we needed. We would definitely stay here again."
United States
Chris
$356 nightly
The price is $395
Sep 12 - Sep 13
Total with taxes and fees
Two Spectacular Ocean Views from the Living Room and Master Bedroom of the Condo
Coffee/tea maker, fridge, microwave, oven

14. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
9.8 out of 10, Exceptional, (220 reviews)
"Our host was amazing! Great location with lots to do! "
United States
Jamie B.
$514 nightly
The price is $570
Aug 24 - Aug 25
Total with taxes and fees
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Beach nearby

15. 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.
$406 nightly
The price is $440
Aug 15 - Aug 16
Total with taxes and fees
Marina to Ocean View Key Largo Ocean Pointe 5308
Exterior

16. Paradise Palms 2 Bedroom Condo Ocean Pointe 1206

Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Tavernier
9.8 out of 10, Exceptional, (6 reviews)
"Super clean and neat location!"
United States
Christopher R.
$415 nightly
The price is $450
Aug 17 - Aug 18
Total with taxes and fees
Paradise Palms 2 Bedroom Condo Ocean Pointe 1206
Beach nearby

17. 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, (10 reviews)
"Such a beautiful condo! We loved our stay."
United States
Bethany B.
$413 nightly
The price is $448
Aug 23 - Aug 24
Total with taxes and fees
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Exterior

18. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (36 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
$277 nightly
The price is $307
Sep 2 - Sep 3
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
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.
$381 nightly
The price is $415
Aug 16 - Aug 17
Total with taxes and fees
Boho Chic Ocean Pointe 3214 King & Queen
Beach nearby

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.
$400 nightly
The price is $435
Aug 16 - Aug 17
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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Loved it!"
Eitan 3-night trip
Posted 2 hours ago
Cheeca Lodge & Spa

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 $144 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 408 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.