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Featured Holiday Homes in Islamorada

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Key Largo
With a stay at this vacation home in Key Largo, you'll be a 4-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral Reef State ...
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Tavernier
When you stay at this vacation home in Tavernier, you'll be on the beach, within a 5-minute drive of Old Road Gallery and Islamorada County Park.
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 out of 5
Key Largo
When you stay at this vacation home in Key Largo, you'll be by the sea, within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo
Located in Key Largo, this vacation home is within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Islamorada
With a stay at this vacation home in Islamorada (Matecumbe), you'll be steps from Anne's Beach and Sunset Drive Beach.
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool
Islamorada Boaters Paradise with 70' Dock and private beach access..

Islamorada Boaters Paradise with 70' Dock and private beach access..

Islamorada
With a stay at this vacation home in Islamorada (Matecumbe), you'll be within a 5-minute drive of Sunset Drive Beach and Anne's Beach.
Islamorada Boaters Paradise with 70' Dock and private beach access..
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada
With a stay at this vacation home in Islamorada (Matecumbe), you'll be within a 5-minute drive of San Pedro Underwater Archaeological Preserve State Park and ...
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Tavernier
With a stay at this vacation home in Tavernier (Blue Waters), you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and Harry Harris Park.
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
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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.

Islamorada Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Islamorada vacation homes are the perfect way for you to wing it.

Holiday houses in Islamorada let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Islamorada in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Islamorada adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Islamorada with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Islamorada vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Islamorada Holiday Homes essential information

Accommodation
687 Holiday Homes
Lowest Price
AU$668
Highest Price
AU$830
Popular accommodation
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly, Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool, Islamorada Boaters Paradise with 70' Dock and private beach access.., Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada, Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Top trending hotels in Islamorada

Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$689 per night from 11 Feb to 12 Feb
AU$689
includes taxes & fees
11 Feb - 12 Feb
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and 13 minutes by foot from Indian Key Historic ...
Amara Cay Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$830 per night from 6 Feb to 7 Feb
AU$830
includes taxes & fees
6 Feb - 7 Feb
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$668 per night from 4 Feb to 5 Feb
AU$668
includes taxes & fees
4 Feb - 5 Feb
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State ...
Chesapeake Beach Resort
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Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$693 per night from 9 Feb to 10 Feb
AU$693
includes taxes & fees
9 Feb - 10 Feb
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery ...
Islander Resort
Don't see what you're looking for?
See all available properties in Islamorada
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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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^Subject to availability and chosen travel dates.