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 FL
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 ...
Opens in a new windowBRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
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
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 ...
Opens in a new windowWaterfront - Private Lagoon - in Park on the Ocean side -beach, pool
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 Jimmy Johnson's Big Chill and John Pennekamp Coral Reef ...
Opens in a new windowBEACHFRONT POOL HOME
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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 Jimmy Johnson's Big Chill and John Pennekamp Coral Reef ...
Opens in a new windowLuxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.
Updated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access

Updated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access

Key Largo FL
When you stay at this vacation home in Key Largo, you'll be by the sea, a 4-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral ...
Opens in a new windowUpdated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access
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 Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
Opens in a new windowMariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10

Key Largo FL
When you stay at this vacation home in Key Largo, you'll be on the waterfront, within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral ...
Opens in a new windowSunrise Escape - Ocean Front Villa - Sleeps 10
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

Key Largo FL
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 11 minutes from John Pennekamp ...
Opens in a new windowNEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hot Tub, 4 H Mini-Golf & Pedal Boat.

Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hot Tub, 4 H Mini-Golf & Pedal Boat.

Tavernier FL
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.
Opens in a new windowLuxury 4B/3B, Private Canal, Kayaks, 13 ft Hot Tub, 4 H Mini-Golf & 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
691 Holiday Homes
Lowest Price
AU$386
Highest Price
AU$522
Popular accommodation
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, BEACHFRONT POOL HOME, Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo., Updated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Sunrise Escape - Ocean Front Villa - Sleeps 10, NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES, Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hot Tub, 4 H Mini-Golf & Pedal Boat.

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$386 per night from 21 May to 22 May
AU$386
21 May - 22 May
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
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$522 per night from 31 May to 1 June
AU$522
31 May - 1 June
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is AU$392 per night from 19 May to 20 May
AU$392
19 May - 20 May
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
Save an average of 15% on thousands of hotels when you're signed in
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$414 per night from 18 May to 19 May
AU$414
18 May - 19 May
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
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.