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
Stay at this beach holiday home in Key Largo. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowBRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
Villa hermosa

Villa hermosa

Key Largo FL
Stay at this beach holiday home in Key Largo. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowVilla hermosa
Updated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access

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

Key Largo FL
Stay at this holiday home in Key Largo. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowUpdated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access
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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
Stay at this holiday home in Key Largo. Enjoy a garden, laundry facilities and patios. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral ...
Opens in a new windowWaterfront - Private Lagoon - in Park on the Ocean side -beach, pool
BEACHFRONT POOL HOME

BEACHFRONT POOL HOME

Key Largo FL
Stay at this beach holiday home in Key Largo. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Jimmy Johnson's Big Chill and Bluefin Rock ...
Opens in a new windowBEACHFRONT POOL HOME
Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10

Key Largo FL
Stay at this family-friendly holiday home in Key Largo. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jimmy Johnson's Big Chill and ...
Opens in a new windowSunrise Escape - Ocean Front Villa - Sleeps 10
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo FL
Stay at this family-friendly holiday home in Key Largo. Enjoy a fitness centre, laundry facilities and concierge services. Popular attractions Jimmy Johnson's ...
Opens in a new windowMariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Villa La Dorada.

Villa La Dorada.

Key Largo FL
Stay at this holiday home in Key Largo. Enjoy a garden, laundry facilities and air conditioning. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowVilla La Dorada.
Anglers Reef Islamorada  home with ocean views, private marina, beach & pool

Anglers Reef Islamorada home with ocean views, private marina, beach & pool

Islamorada FL
Stay at this beach holiday home in Islamorada. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Windley Key Fossil Reef Geological State ...
Opens in a new windowAnglers Reef Islamorada home with ocean views, private marina, beach & pool
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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
679 Holiday Homes
Lowest Price
NZ$471
Highest Price
NZ$544
Popular accommodation
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART, Villa hermosa, Updated Key Largo Townhome • Pool • Saltwater Lagoon • Beach • Oceanfront Access, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, BEACHFRONT POOL HOME, Sunrise Escape - Ocean Front Villa - Sleeps 10, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Villa La Dorada., Anglers Reef Islamorada home with ocean views, private marina, beach & pool

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 NZ$503 per night from 2 June to 3 June
NZ$503
2 June - 3 June
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
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 NZ$471 per night from 2 June to 3 June
NZ$471
2 June - 3 June
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowChesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$526 per night from 23 June to 24 June
NZ$526
23 June - 24 June
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
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
Fully refundableReserve now, pay when you stay
The price is NZ$544 per night from 1 June to 2 June
NZ$544
1 June - 2 June
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
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.

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