Book Holiday Homes in Islamorada

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Islamorada

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 ...
VOTED BEST KEY LARGO VACATION RENTAL
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

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

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 ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

Islamorada
With a stay at this vacation home in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State ...
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Save an average of 15% on thousands of hotels when you're signed in
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

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

Tavernier
When you stay at this vacation home in Tavernier, you'll be on the beach, within a 5-minute drive of Old Road Gallery and Islamorada County Park.
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
811 Mariners Club Key Largo | 4 Bed, 3 Bath

811 Mariners Club Key Largo | 4 Bed, 3 Bath

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 10-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor Marina.
811 Mariners Club Key Largo | 4 Bed, 3 Bath
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 ...
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
701 Mariners Club Key Largo | 3 Bed, 3.5 Bath

701 Mariners Club Key Largo | 3 Bed, 3.5 Bath

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor Marina.
701 Mariners Club Key Largo | 3 Bed, 3.5 Bath
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

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

Tavernier
Located in Tavernier (Blue Waters), this vacation home is within a 5-minute drive of Harry Harris Park and Mariners Hospital.
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 10-minute drive of John Pennekamp Coral Reef State Park and Jacob's Aquatic Center.
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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
684 Holiday Homes
Lowest Price
AU$492
Highest Price
AU$586
Popular accommodation
VOTED BEST KEY LARGO VACATION RENTAL, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property, Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly, 811 Mariners Club Key Largo | 4 Bed, 3 Bath, Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools., 701 Mariners Club Key Largo | 3 Bed, 3.5 Bath, Charming Canal-Front House | WiFi+Swim+Kayak+Fish, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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$586 per night from 8 Jan to 9 Jan
AU$586
includes taxes & fees
8 Jan - 9 Jan
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 ...
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 AU$566 per night from 9 Jan to 10 Jan
AU$566
includes taxes & fees
9 Jan - 10 Jan
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 13 minutes by foot from Indian Key Historic ...
Amara Cay Resort
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 AU$492 per night from 20 Jan to 21 Jan
AU$492
includes taxes & fees
20 Jan - 21 Jan
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 ...
Chesapeake Beach Resort
Save an average of 15% on thousands of hotels when you're signed in
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$542 per night from 5 Jan to 6 Jan
AU$542
includes taxes & fees
5 Jan - 6 Jan
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive ...
La Siesta Resort & Villas
Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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.