Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 out of 5
Key Largo
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, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Key Largo Sunset Estate

Key Largo Sunset Estate

Key Largo
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 windowKey Largo Sunset Estate
BEACHFRONT POOL HOME

BEACHFRONT POOL HOME

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the beach, 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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BeachFront Paradise/By The Glam Homes

BeachFront Paradise/By The Glam Homes

Islamorada
Located in Islamorada (Matecumbe), this vacation home is within a 5-minute drive of Sunset Drive Beach and Robbie’s of Islamorada.
Opens in a new windowBeachFront Paradise/By The Glam Homes
VOTED BEST KEY LARGO VACATION RENTAL

VOTED BEST KEY LARGO VACATION RENTAL

Key Largo
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 windowVOTED BEST KEY LARGO VACATION RENTAL
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Key Largo
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 windowKawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
Beautiful Updated Kawama Townhouse.  Marina, boat ramp, lagoon and pools.

Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.

Key Largo
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 windowBeautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.

Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.

Islamorada
With a stay at this vacation home in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 9 minutes by foot from Keys History ...
Opens in a new windowIconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
Villa Valbuena Azul Escape Key Largo 2 Kings, Pickleball

Villa Valbuena Azul Escape Key Largo 2 Kings, Pickleball

Key Largo
With a stay at this vacation home in Key Largo, you'll be a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral Reef State ...
Opens in a new windowVilla Valbuena Azul Escape Key Largo 2 Kings, Pickleball
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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
734 Holiday Homes
Lowest Price
AU$330
Highest Price
AU$655
Popular accommodation
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball, Key Largo Sunset Estate, BEACHFRONT POOL HOME, BeachFront Paradise/By The Glam Homes, VOTED BEST KEY LARGO VACATION RENTAL, Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!, Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools., Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage., Villa Valbuena Azul Escape Key Largo 2 Kings, Pickleball

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$446 per night from 13 Nov to 14 Nov
AU$446
13 Nov - 14 Nov
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$330 per night from 13 Nov to 14 Nov
AU$330
13 Nov - 14 Nov
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$368 per night from 3 Dec to 4 Dec
AU$368
3 Dec - 4 Dec
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
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Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
The price is AU$655 per night from 16 Nov to 17 Nov
AU$655
16 Nov - 17 Nov
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.

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^Subject to availability and chosen travel dates.