Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

BEACHFRONT POOL HOME

BEACHFRONT POOL HOME

Key Largo FL
With a stay at this vacation home in Key Largo (Silver Shores), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Florida Keys National ...
Opens in a new windowBEACHFRONT POOL HOME
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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

Key Largo FL
With a stay at this vacation home in Key Largo, you'll be within a 10-minute drive of John Pennekamp Coral Reef State Park and Jacob's Aquatic Center.
Opens in a new windowCompletely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo FL
With a stay at this vacation home in Key Largo (Rock Harbor), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor ...
Opens in a new windowMariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
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Marina Villa Mariner`s Club 212

Marina Villa Mariner`s Club 212

Key Largo FL
With a stay at this vacation home in Key Largo (Rock Harbor), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor ...
Opens in a new windowMarina Villa Mariner`s Club 212
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

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

Islamorada FL
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 ...
Opens in a new windowBungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Fun For All! Key Largo 3/3 Townhome Oceanside Resort

Fun For All! Key Largo 3/3 Townhome Oceanside Resort

Key Largo FL
With a stay at this vacation home in Key Largo, you'll be on the waterfront, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's ...
Opens in a new windowFun For All! Key Largo 3/3 Townhome Oceanside Resort
Beautiful Oceanside Mariner's 3 Bedroom Townhome

Beautiful Oceanside Mariner's 3 Bedroom Townhome

Key Largo FL
With a stay at this vacation home in Key Largo (Rock Harbor), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor ...
Opens in a new windowBeautiful Oceanside Mariner's 3 Bedroom Townhome
Islamorada Boaters Paradise with 70' Dock and private beach access..

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

Islamorada FL
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.
Opens in a new windowIslamorada Boaters Paradise with 70' Dock and private beach access..
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Key Largo FL
With a stay at this vacation home in Key Largo, you'll be on the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jacob's Aquatic ...
Opens in a new windowBRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
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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
714 Holiday Homes
Lowest Price
AU$400
Highest Price
AU$638
Popular accommodation
BEACHFRONT POOL HOME, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Marina Villa Mariner`s Club 212, Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada, Fun For All! Key Largo 3/3 Townhome Oceanside Resort, Beautiful Oceanside Mariner's 3 Bedroom Townhome, Islamorada Boaters Paradise with 70' Dock and private beach access.., BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Top trending hotels in Islamorada

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$400 per night from 25 Jan to 26 Jan
AU$400
25 Jan - 26 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowChesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$638 per night from 4 Jan to 5 Jan
AU$638
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil ...
Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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$493 per night from 4 Jan to 5 Jan
AU$493
4 Jan - 5 Jan 2026
includes taxes & fees
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 a 2-minute drive from Florida Keys Brewing ...
Opens in a new windowAmara Cay Resort
Save an average of 15% on thousands of hotels when you're signed in
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$610 per night from 4 Jan to 5 Jan
AU$610
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowCheeca Lodge & Spa
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.