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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Islamorada vacation rentals

A beach with thatched umbrellas, palm trees, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
$147 nightly
The price is $165
Nov 15 - Nov 16
Total with taxes and fees
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (184 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
$262 nightly
The price is $295
Nov 16 - Nov 17
Total with taxes and fees
Treasure Harbor
A beach with a thatched umbrella and wooden benches, palm trees, and a clear blue sky.

3. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
$305 nightly
The price is $339
Nov 16 - Nov 17
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
A beach entrance with a sign reading 'Ocean Pointe Marina' and a thatched structure.

4. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (53 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.
$296 nightly
The price is $330
Nov 14 - Nov 15
Total with taxes and fees
Amazing Ocean view condo
A modern hallway with a marble-patterned wall, a white door with a number plate, and a sleek, reflective floor.

5. Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo

Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
Tavernier
9.8 out of 10, Exceptional, (6 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
$252 nightly
The price is $281
Nov 15 - Nov 16
Total with taxes and fees
Cozy 1-bedroom apartment with kitchen in peaceful Tavernier/Key largo
A beach with palm trees, thatched umbrellas, and sun loungers.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (172 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.
$322 nightly
The price is $358
Nov 15 - Nov 16
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a yellow tablecloth.

7. Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
10.0 out of 10, Exceptional, (41 reviews)
"Very clean and nice location."
United States
Melinda V.
$315 nightly
The price is $351
Nov 15 - Nov 16
Total with taxes and fees
Charming Home in Key Largo
A wooden deck with a thatched roof, wooden chairs, and tables, overlooking a clear blue sea.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (116 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$332 nightly
The price is $368
Nov 19 - Nov 20
Total with taxes and fees
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
A beach with palm trees, thatched umbrellas, and blue lounge chairs.

9. Flamingo Flats | Marina View | Ocean Pointe 5306

Flamingo Flats | Marina View | Ocean Pointe 5306
Tavernier
9.6 out of 10, Exceptional, (9 reviews)
"Great location and prompt support with all questions we had. "
United States
Jim I.
$395 nightly
The price is $430
Nov 15 - Nov 16
Total with taxes and fees
Flamingo Flats | Marina View | Ocean Pointe 5306
A beach with palm trees, thatched umbrellas, and sun loungers.

10. 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.
$464 nightly
The price is $511
Nov 18 - Nov 19
Total with taxes and fees
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
A wooden deck with chairs and a table, overlooking the ocean.

11. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
8.6 out of 10, Excellent, (46 reviews)
"Wonderful stay! Beautiful view from the balcony"
United States
Katy T.
$343 nightly
The price is $383
Nov 14 - Nov 15
Total with taxes and fees
Ocean view condo with balcony/marina view
A beach with palm trees, thatched umbrellas, and blue lounge chairs.

12. Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Aqua Vista | Ocean View 2BR | 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
$394 nightly
The price is $429
Nov 15 - Nov 16
Total with taxes and fees
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
A beach with palm trees, thatched umbrellas, and blue lounge chairs.

13. 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)
"My host is amazing and the property was incredible. Highly recommended."
United States
Jean V.
$427 nightly
The price is $466
Nov 17 - Nov 18
Total with taxes and fees
Lazy Daze | Double King Suite | Ocean Pointe 2310
A beach with rows of blue lounge chairs, a thatched hut, and a wooden walkway leading to the water.

14. 2BR Condo w/ Ocean View, Pool & Tropical Setting

2BR Condo w/ Ocean View, Pool & Tropical Setting
Tavernier
9.6 out of 10, Exceptional, (4 reviews)
" centrally located for keys travel"
United States
Gary
$408 nightly
The price is $455
Nov 30 - Dec 1
Total with taxes and fees
2BR Condo w/ Ocean View, Pool & Tropical Setting
A beach with rows of sun loungers, a wooden pier, and a thatched-roof structure.

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
$401 nightly
The price is $447
Nov 16 - Nov 17
Total with taxes and fees
Your Happy Place - gorgeous 2 bed/2 bath oceanfront suite with full kitchen
A beach with palm trees, thatched umbrellas, and blue lounge chairs.

16. Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Tavernier
9.8 out of 10, Exceptional, (20 reviews)
"Great stay"
United States
Blain R.
$403 nightly
The price is $439
Nov 16 - Nov 17
Total with taxes and fees
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
A wooden deck with a thatched roof and two Adirondack chairs facing the ocean.

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, (103 reviews)
"Great visit!"
United States
Leigh D. H.
$321 nightly
The price is $359
Nov 15 - Nov 16
Total with taxes and fees
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
A swimming pool with lounge chairs and umbrellas, surrounded by trees.

18. Signature 1BR Partial Ocean View | Beach + Pool

Signature 1BR Partial Ocean View | Beach + Pool
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Beautiful place, nice location"
United States
Michelle G.
$194 nightly
The price is $216
Nov 30 - Dec 1
Total with taxes and fees
Signature 1BR Partial Ocean View | Beach + Pool
A beach with palm trees, thatched umbrellas, and blue lounge chairs.

19. Tiki Time | Top Floor King | Ocean Pointe 1413

Tiki Time | Top Floor King | Ocean Pointe 1413
Tavernier
10.0 out of 10, Exceptional, (2 reviews)
"The host was excellent, they reached out often and very attentive. The condo is beautifully decorated and super clean. It is a small condo but perfect for a couple. It has numerous amenities and has lots of extras for your use. We would definitely stay here again!"
United States
Constance W.
$372 nightly
The price is $405
Nov 29 - Nov 30
Total with taxes and fees
Tiki Time | Top Floor King | Ocean Pointe 1413
A beach with palm trees, thatched umbrellas, and blue lounge chairs.

20. Starfish Seas | Ocean View | Ocean Pointe 1302

Starfish Seas | Ocean View | Ocean Pointe 1302
Tavernier
9.8 out of 10, Exceptional, (30 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.
$409 nightly
The price is $448
Nov 18 - Nov 19
Total with taxes and fees
Starfish Seas | Ocean View | Ocean Pointe 1302
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

10/10 Excellent
"I loved having a balcony to sit on to view the water. It was perfect for morning coffee or an afternoon to read. The breakfast every morning was perfect, and provided healthy options like fruit and yogurt. I tried a bite of my husband’s omelette and it was excellent. All the staff was friendly and helpful. Thank you for a nice stay!"
Lauren 6-night trip
Posted 4 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 $165 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?

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This Islamorada vacation home rental offers an outdoor pool, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind. Some other homes for rent in Islamorada include 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

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?

Anne's Beach and Fiesta Key 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.