Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

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 ...
Opens in a new windowWaterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Fall Deals & Spring Openings - Cozy 4BR Key Largo Escape in Mariners Club!

Fall Deals & Spring Openings - Cozy 4BR Key Largo Escape in Mariners Club!

Key Largo
The price is AU$1,618 per night from 30 Sept to 1 Oct
AU$1,618
30 Sept - 1 Oct
includes taxes & fees
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 ...
Opens in a new windowFall Deals & Spring Openings - Cozy 4BR Key Largo Escape in Mariners Club!
Next availability from May 18th, 2024  - The Last Resort, Islamorada - MM76.7

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Islamorada, FL
With a stay at this vacation home in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and 3 minutes by foot from San Pedro Underwater Archaeological ...
Opens in a new windowNext availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
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OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

Islamorada
When you stay at this vacation home in Islamorada, you'll be on the beach, within a 5-minute drive of Windley Key Fossil Reef Geological State Park and Rain ...
Opens in a new windowOCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
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.
Opens in a new windowMariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Opens in a new windowResort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina

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 9 minutes from John Pennekamp Coral Reef State ...
Opens in a new windowKawama L4 - Upscale Oceanside Villa with Marina
Beautiful Oceanside Mariner's 3 Bedroom Townhome

Beautiful Oceanside Mariner's 3 Bedroom Townhome

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 3-minute drive from Jimmy Johnson's Big Chill and 10 minutes from John Pennekamp ...
Opens in a new windowBeautiful Oceanside Mariner's 3 Bedroom Townhome
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 ...
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
732 Holiday Homes
Lowest Price
AU$248
Highest Price
AU$1,618
Popular accommodation
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Fall Deals & Spring Openings - Cozy 4BR Key Largo Escape in Mariners Club!, Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!, Kawama L4 - Upscale Oceanside Villa with Marina, Beautiful Oceanside Mariner's 3 Bedroom Townhome, BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Top trending hotels in Islamorada

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$248 per night from 8 Oct to 9 Oct
AU$248
8 Oct - 9 Oct
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
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$290 per night from 29 Sept to 30 Sept
AU$290
29 Sept - 30 Sept
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
Fully refundableReserve now, pay when you stay
The price is AU$373 per night from 1 Oct to 2 Oct
AU$373
1 Oct - 2 Oct
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$425 per night from 2 Oct to 3 Oct
AU$425
2 Oct - 3 Oct
includes taxes & fees
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 ...
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.