Islamorada Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Islamorada vacation rentals

25-inch flat-screen TV with digital channels, TV
Treasure Harbor

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (123 reviews)
"Great spot! Will be back someday hopefully. "
Canada
Diane
$274 nightly
The price is $308
Jan 13 - Jan 14
Total with taxes and fees
Treasure Harbor
Exterior
Breezy Palms Resort

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (606 reviews)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
$219 nightly
The price is $247
Jan 14 - Jan 15
Total with taxes and fees
Breezy Palms Resort
On the beach, sun loungers, beach umbrellas, beach towels
The Islands of Islamorada

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveler
$602 nightly
The price is $677
Jan 13 - Jan 14
Total with taxes and fees
The Islands of Islamorada
Property grounds
Boho Style Florida Keys Condo Ocean Views

Apartment in Tavernier

Boho Style Florida Keys Condo Ocean Views
9.8 out of 10, Exceptional, (43 reviews)
"Would stay there again."
Canada
jamie g.
$439 nightly
The price is $488
Jan 28 - Jan 29
Total with taxes and fees
Boho Style Florida Keys Condo Ocean Views
Marina
Island Sanctuary Islamorada

Houseboat in Tavernier

Island Sanctuary Islamorada
9.8 out of 10, Exceptional, (13 reviews)
"It exceeded our expectations, and we are so glad we found this location!"
United States
Jenn H.
$360 nightly
The price is $401
Jan 20 - Jan 21
Total with taxes and fees
Island Sanctuary Islamorada
Beach
Aqua Vista Ocean Pointe 3307

Condo in Tavernier

Aqua Vista Ocean Pointe 3307
2.5 star property
10.0 out of 10, Exceptional, (1 review)
"Beautiful & perfect place for a getaway. Really enjoyed our stay. Highly recommend."
United States
Michelle
$447 nightly
The price is $488
Feb 1 - Feb 2
Total with taxes and fees
Aqua Vista Ocean Pointe 3307
Fridge, microwave, oven, stovetop
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Houseboat in Tavernier

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
9.8 out of 10, Exceptional, (210 reviews)
"Absolutely wonderful property in every way!"
United States
Christopher K.
$454 nightly
The price is $504
Jan 16 - Jan 17
Total with taxes and fees
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
On the beach, sun loungers, beach towels
Coastal comfort in Ocean Pointe Suites.

Condo in Tavernier

Coastal comfort in Ocean Pointe Suites.
10.0 out of 10, Exceptional, (33 reviews)
"Very clean, lots of things to do for the kids on property - large pool and hot tub, tennis and pickle ball courts, and a small beach. "
United States
Robert F.
$601 nightly
The price is $667
Jan 13 - Jan 14
Total with taxes and fees
Coastal comfort in Ocean Pointe Suites.
Property grounds
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Vacation Home in Key Largo

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
2.0 star property
10.0 out of 10, Exceptional, (46 reviews)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
$528 nightly
The price is $587
Jan 13 - Jan 14
Total with taxes and fees
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Interior
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!

Condo in Tavernier

Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The property was just as pictured on the site! We loved the view from the balconies (yes, two!!!). The host was superior in supplying our basic needs upon arrival. More importantly, she was extremely responsive to our questions during our stay (usually responding within a few minutes--even on Christmas day!!). The property is conveniently located in the keys so it's not too far to Miami or Key West. We absolutely loved our stay! If we come back to the Keys, we will definitely stay here again!!!"
United States
Mark W.
$361 nightly
The price is $402
Jan 19 - Jan 20
Total with taxes and fees
Top Floor w Amazing Ocean Views!! Resort Style Pool, Beach, Marina, & Cafe!
Beach
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony

Condo in Blue Waters

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully high-end decorated & furnished like brand new! Very clean and appointed with everything one could want for a perfect stay. First floor convenience (building elevated on piers) but no water view Would definitely return! "
United States
Peter A. Z.
$426 nightly
The price is $465
Jan 27 - Jan 28
Total with taxes and fees
Island Time at Ocean Pointe Luxe 2 King Spa BR/BA, 2 Balcony
Beach
2BR Condo w/ Ocean Views, Private Beach & Pool

Condo in Tavernier

2BR Condo w/ Ocean Views, Private Beach & Pool
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"A good place to relax."
United States
gildas m.
$442 nightly
The price is $491
Jan 13 - Jan 14
Total with taxes and fees
2BR Condo w/ Ocean Views, Private Beach & Pool
Beach
Sea View Farm Style Ocean front Condo Views

Condo in Tavernier

Sea View Farm Style Ocean front Condo Views
10.0 out of 10, Exceptional, (157 reviews)
"The property was excellent."
United States
June M.
$401 nightly
The price is $446
Jan 19 - Jan 20
Total with taxes and fees
Sea View Farm Style Ocean front Condo Views
Beach
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen

Condo in Tavernier

Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Great place! Condo was clean l and was as described. Property and pool area was fun and very clean."
United States
Kevin W.
$410 nightly
The price is $445
Jan 14 - Jan 15
Total with taxes and fees
Ocean View Gem Ocean Pointe 3406 2BA/2BR King/Queen
Beach nearby
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411

Apartment in Tavernier

Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
10.0 out of 10, Exceptional, (4 reviews)
"The condo was very clean, comfortable and had everything we needed. We appreciated the close location to the pool. "
United States
Erica T.
$437 nightly
The price is $476
Feb 2 - Feb 3
Total with taxes and fees
Sunrise Oasis - Top Floor 2 BR 2 BA Condo 2411
Interior
Private 3-bedroom brand new apartment in Tavernier, Key Largo

Apartment in Tavernier

Private 3-bedroom brand new apartment in Tavernier, Key Largo
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The amenities and location were nice for being close to Key Largo. There is a small park that faces the Atlantic side which is a 1 minute walk from the apartment. "
United States
Kathleen A.
$522 nightly
The price is $580
Jan 14 - Jan 15
Total with taxes and fees
Private 3-bedroom brand new apartment in Tavernier, Key Largo
On the beach
Serenity In The Sun Condo Fabulous Ocean View

Condo in Tavernier

Serenity In The Sun Condo Fabulous Ocean View
10.0 out of 10, Exceptional, (108 reviews)
"Fantastic place to stay! Very clean and great hosts. Will stay again. "
United States
Les
$424 nightly
The price is $471
Jan 21 - Jan 22
Total with taxes and fees
Serenity In The Sun Condo Fabulous Ocean View
On the beach, sun loungers, beach towels
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

Vacation Home in Key Largo

NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
9.8 out of 10, Exceptional, (170 reviews)
"Everything was clean and in good condition. The owner responded right away to any questions. Golf Cart is a plus! "
United States
Anonymous traveler
$1,035 nightly
The price is $1,150
Jan 29 - Jan 30
Total with taxes and fees
NEW! CASA PALMA OCEANSIDE -GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Interior
Boho Chic Ocean Pointe 3214

Apartment in Tavernier

Boho Chic Ocean Pointe 3214
10.0 out of 10, Exceptional, (12 reviews)
"It was clean, well organized and communication was great. Had a good time."
United States
Shirl
$422 nightly
The price is $462
Jan 27 - Jan 28
Total with taxes and fees
Boho Chic Ocean Pointe 3214
Terrace/patio
Spectacular Ocean-Marina Views - Free Kayaks Pickleball

Apartment in Key Largo

Spectacular Ocean-Marina Views - Free Kayaks Pickleball
$779 nightly
The price is $865
Feb 9 - Feb 10
Total with taxes and fees
Spectacular Ocean-Marina Views - Free Kayaks Pickleball
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
"The king suite with ocean view was fantastic. The resort is in good shape with plenty of space to lounge, activities and includes nice breakfast options. Also close to many bars and restaurants. "
Randy 4-night trip
Posted 18 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 $247 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 close to well known points of interest in Islamorada, or you can choose a more remote option if you're looking for 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 barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Some other homes for rent in Islamorada include Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada.

How many vacation rentals are there in Islamorada?

With 486 Expedia vacation rentals, you're sure to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Founders Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

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.