Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

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 Jacob's Aquatic ...
Opens in a new windowWaterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

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 Jacob's Aquatic ...
Opens in a new windowRefined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

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 Jimmy Johnson's ...
Opens in a new windowNEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
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Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

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

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 windowWaterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.

Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.

Key Largo FL
With a stay at this vacation home in Key Largo (Sunrise Point), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Florida Keys National ...
Opens in a new windowLuxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.
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
Beautiful Key Largo Town Home Fully Renovated Top to Bottom

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

Key Largo FL
With a stay at this vacation home in Key Largo, you'll be by the ocean, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jacob's Aquatic ...
Opens in a new windowBeautiful Key Largo Town Home Fully Renovated Top to Bottom
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
Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.

Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.

Tavernier FL
Located in Tavernier (Blue Waters), this vacation home is within a 5-minute drive of Harry Harris Park and Mangrove Marina.
Opens in a new windowLuxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.
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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$484
Highest Price
AU$759
Popular accommodation
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball, Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests, NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo., Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo., Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada, Beautiful Key Largo Town Home Fully Renovated Top to Bottom, BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART, Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.

Top trending hotels in Islamorada

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$759 per night from 13 Apr to 14 Apr
AU$759
13 Apr - 14 Apr
includes taxes & fees
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing ...
Opens in a new windowCheeca Lodge & Spa
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$484 per night from 14 Apr to 15 Apr
AU$484
14 Apr - 15 Apr
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
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$503 per night from 20 Apr to 21 Apr
AU$503
20 Apr - 21 Apr
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AU$593 per night from 22 Apr to 23 Apr
AU$593
22 Apr - 23 Apr
includes taxes & fees
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 7 minutes by foot from Islamorada Brewery ...
Opens in a new windowIslander 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.

Top Picks

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^Subject to availability and chosen travel dates.