Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

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 Bluefin Rock Harbor Marina and Pigeon Key ...
Opens in a new windowBEACHFRONT POOL HOME
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Key Largo FL
Stay at this holiday home in Key Largo. Enjoy free Wi-Fi, laundry facilities and cable/satellite TV service. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowCompletely Remodeled 3/3 in the heart of Key Largo (Oceanside)
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 John Pennekamp ...
Opens in a new windowMariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
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Marina Villa Mariner`s Club 212

Marina Villa Mariner`s Club 212

Key Largo FL
The price is NZ$1,521 per night from 24 Dec to 25 Dec
NZ$1,521
24 Dec - 25 Dec
includes taxes & fees
Stay at this holiday home in Key Largo. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions John Pennekamp Coral Reef State Park and Bluefin ...
Opens in a new windowMarina Villa Mariner`s Club 212
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Robbie’s of Islamorada and Indian Key Historic ...
Opens in a new windowBungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Fun For All! Key Largo 3/3 Townhome Oceanside Resort

Fun For All! Key Largo 3/3 Townhome Oceanside Resort

Key Largo FL
Stay at this family-friendly holiday home in Key Largo. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions John Pennekamp Coral Reef ...
Opens in a new windowFun For All! Key Largo 3/3 Townhome Oceanside Resort
Beautiful Oceanside Mariner's 3 Bedroom Townhome

Beautiful Oceanside Mariner's 3 Bedroom Townhome

Key Largo FL
Stay at this holiday home in Key Largo. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions John Pennekamp Coral Reef State Park and ...
Opens in a new windowBeautiful Oceanside Mariner's 3 Bedroom Townhome
Islamorada Boaters Paradise with 70' Dock and private beach access..

Islamorada Boaters Paradise with 70' Dock and private beach access..

Islamorada FL
Stay at this holiday home in Islamorada. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Sunset Drive Beach and Anne's Beach are ...
Opens in a new windowIslamorada Boaters Paradise with 70' Dock and private beach access..
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 John Pennekamp Coral Reef State Park and Jacob's ...
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
714 Holiday Homes
Lowest Price
NZ$465
Highest Price
NZ$1,521
Popular accommodation
BEACHFRONT POOL HOME, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Marina Villa Mariner`s Club 212, Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada, Fun For All! Key Largo 3/3 Townhome Oceanside Resort, Beautiful Oceanside Mariner's 3 Bedroom Townhome, Islamorada Boaters Paradise with 70' Dock and private beach access.., BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

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 NZ$465 per night from 22 Dec to 23 Dec
NZ$465
22 Dec - 23 Dec
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
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is NZ$573 per night from 8 Jan to 9 Jan
NZ$573
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy a private beach, 3 bars/lounges and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
Opens in a new windowAmara Cay 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 NZ$1,176 per night from 11 Jan to 12 Jan
NZ$1,176
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
Opens in a new windowCheeca Lodge & Spa
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$626 per night from 4 Jan to 5 Jan
NZ$626
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.