Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

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

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

Key Largo
Stay at this vacation home in Key Largo. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Our guests praise the helpful staff in our ...
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Key Largo
Stay at this vacation home in Key Largo. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions John Pennekamp Coral Reef State Park and ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Tavernier
Book a stay at this beach vacation home in Tavernier. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Old Road Gallery and Founders Park ...
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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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
Book a stay at this family-friendly vacation home in Key Largo. Enjoy 4 outdoor pickleball courts, a water park, and a fitness center. Popular attractions John ...
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo
Stay at this vacation home in Key Largo. Enjoy a fitness center, concierge services, and tennis courts. Popular attractions Jimmy Johnson's Big Chill and John ...
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Islamorada
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool
Islamorada Boaters Paradise with 70' Dock and private beach access..

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

Islamorada
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and patios. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
Islamorada Boaters Paradise with 70' Dock and private beach access..
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Tavernier
Stay at this vacation home in Tavernier. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Harry Harris Park and Florida Keys Dive ...
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

Key Largo
Book a stay at this family-friendly vacation home in Key Largo. Enjoy a fitness center, cable/satellite TV service, and in-room jetted tubs. Popular attractions ...
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More
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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
687 Holiday Homes
Lowest Price
NZ$703
Highest Price
NZ$899
Popular accommodation
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly, Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool, Islamorada Boaters Paradise with 70' Dock and private beach access.., Charming Canal-Front House | WiFi+Swim+Kayak+Fish, 4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

Top trending hotels in Islamorada

Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$703 per night from 24 Feb to 25 Feb
NZ$703
includes taxes & fees
24 Feb - 25 Feb
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
Chesapeake Beach Resort
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 NZ$899 per night from 2 Mar to 3 Mar
NZ$899
includes taxes & fees
2 Mar - 3 Mar
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 ...
Cheeca Lodge & Spa
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$775 per night from 25 Feb to 26 Feb
NZ$775
includes taxes & fees
25 Feb - 26 Feb
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
Amara 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$794 per night from 27 Feb to 28 Feb
NZ$794
includes taxes & fees
27 Feb - 28 Feb
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Islander 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.