Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

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
When you stay at this vacation home in Key Largo, you'll be on the beach, a 3-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral ...
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
NEW LISTING! -Waterfront (Private Lagoon) in Park on the Ocean side -beach, pool

NEW LISTING! -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 ...
NEW LISTING! -Waterfront (Private Lagoon) in Park on the Ocean side -beach, pool
beautiful villa

beautiful villa

Key Largo
The price is AU$776 per night from 2 May to 3 May
AU$776
per night
2 May - 3 May
When you stay at this vacation home in Key Largo, you'll be by the sea, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
beautiful villa
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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)
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

Islamorada
Located in Islamorada, this vacation home is by the ocean, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Founders Park.
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the beach, a 3-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral ...
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
Peacock Shores Islamorada - Vacation On The Beach!

Peacock Shores Islamorada - Vacation On The Beach!

Islamorada
Located in Islamorada, this vacation home is by the ocean, within a 5-minute drive of Islamorada County Park and Florida Keys Dive Center.
Peacock Shores Islamorada - Vacation On The Beach!
GREAT LOCATION! VILLA R5,MARINA, BEACH, LAGOON, 2POOLS,TENNIS,KAYAKS&BIKES

GREAT LOCATION! VILLA R5,MARINA, BEACH, LAGOON, 2POOLS,TENNIS,KAYAKS&BIKES

Key Largo
With a stay at this vacation home, you'll be centrally located in Key Largo, a 4-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
GREAT LOCATION! VILLA R5,MARINA, BEACH, LAGOON, 2POOLS,TENNIS,KAYAKS&BIKES
Key Largo Resort Townhouse with all the toys

Key Largo Resort Townhouse with all the toys

Key Largo
With a stay at this vacation home in Key Largo, you'll be a 3-minute drive from Jimmy Johnson's Big Chill and 10 minutes from John Pennekamp Coral Reef State ...
Key Largo Resort Townhouse with all the toys
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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
492 Holiday Homes
Lowest Price
AU$343
Highest Price
AU$776
Popular accommodation
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART, NEW LISTING! -Waterfront (Private Lagoon) in Park on the Ocean side -beach, pool, beautiful villa , Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach, VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS, Peacock Shores Islamorada - Vacation On The Beach!, GREAT LOCATION! VILLA R5,MARINA, BEACH, LAGOON, 2POOLS,TENNIS,KAYAKS&BIKES, Key Largo Resort Townhouse with all the toys

Top trending hotels in Islamorada

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$343 per night from 30 Apr to 1 May
AU$343
per night
30 Apr - 1 May
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
Cheeca Lodge & Spa

Cheeca Lodge & Spa

4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$567 per night from 12 May to 13 May
AU$567
per night
12 May - 13 May
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 6 minutes by foot from Florida ...
Cheeca Lodge & Spa
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$455 per night from 12 May to 13 May
AU$455
per night
12 May - 13 May
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
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La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$504 per night from 7 May to 8 May
AU$504
per night
7 May - 8 May
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive ...
La Siesta Resort & Villas
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.