Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

Key Largo FL
Stay at this holiday home in Key Largo. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions John Pennekamp Coral Reef State Park and Jacob's ...
Opens in a new windowWaterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

Key Largo FL
Stay at this holiday home in Key Largo. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions John Pennekamp Coral Reef State Park and ...
Opens in a new windowRefined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Key Largo FL
Stay at this beach holiday home in Key Largo. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions John Pennekamp Coral Reef State Park and ...
Opens in a new windowNEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
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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 John Pennekamp Coral Reef State Park and Jacob's Aquatic ...
Opens in a new windowWaterfront - Private Lagoon - in Park on the Ocean side -beach, pool
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
Stay at this holiday home in Key Largo. Enjoy private pools, a fitness centre and a garden. Popular attractions Harry Harris Park and Pigeon Key are located ...
Opens in a new windowLuxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.
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
Beautiful Key Largo Town Home Fully Renovated Top to Bottom

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

Key Largo FL
Stay at this family-friendly holiday home in Key Largo. Enjoy private pools, laundry facilities and tennis courts. Popular attractions John Pennekamp Coral Reef ...
Opens in a new windowBeautiful Key Largo Town Home Fully Renovated Top to Bottom
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
Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.

Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.

Tavernier FL
Stay at this holiday home in Tavernier. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Harry Harris Park and Mangrove Marina are ...
Opens in a new windowLuxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & 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
714 Holiday Homes
Lowest Price
NZ$580
Highest Price
NZ$709
Popular accommodation
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball, Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests, NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo., Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo., Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada, Beautiful Key Largo Town Home Fully Renovated Top to Bottom, BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART, Luxury 4B/3B, Private Canal, Kayaks, 13 ft Hydrotherapy Swim Spa & Pedal Boat.

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$658 per night from 29 Apr to 30 Apr
NZ$658
29 Apr - 30 Apr
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$580 per night from 14 Apr to 15 Apr
NZ$580
14 Apr - 15 Apr
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$602 per night from 20 Apr to 21 Apr
NZ$602
20 Apr - 21 Apr
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
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Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NZ$709 per night from 22 Apr to 23 Apr
NZ$709
22 Apr - 23 Apr
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
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.