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

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

Islamorada
With a stay at this vacation home in Islamorada (Venetian Shores), you'll be within a 5-minute drive of Rain Barrel Village and Islamorada County Park.
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Charming Home in Key Largo

Charming Home in Key Largo

Key Largo
The price is AU$609 per night from 18 Aug to 19 Aug
AU$609
18 Aug - 19 Aug
includes taxes & fees
Located in Key Largo, this vacation home is within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Charming Home in Key Largo
Next availability from May 18th, 2024  - The Last Resort, Islamorada - MM76.7

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Islamorada, FL
With a stay at this vacation home in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and 3 minutes by foot from San Pedro Underwater Archaeological ...
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Save an average of 15% on thousands of hotels when you're signed in
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 out of 5
Key Largo
Located in Key Largo, this vacation home is within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
208 Mariners Club Key Largo | 3 Bed, 3 Bath

208 Mariners Club Key Largo | 3 Bed, 3 Bath

Key Largo
When you stay at this vacation home in Key Largo, you'll be by the sea, a 3-minute drive from Jimmy Johnson's Big Chill and 10 minutes from John Pennekamp Coral ...
208 Mariners Club Key Largo | 3 Bed, 3 Bath
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

Key Largo
When you stay at this vacation home in Key Largo, you'll be by the sea, within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

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

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo
Located in Key Largo, this vacation home is within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Still time for that last minute summer glow! Stay w us @ Mariner's Club 606

Still time for that last minute summer glow! Stay w us @ Mariner's Club 606

Key Largo
The price is AU$1,382 per night from 17 Aug to 18 Aug
AU$1,382
17 Aug - 18 Aug
includes taxes & fees
When you stay at this vacation home in Key Largo, you'll be by the sea, within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
Still time for that last minute summer glow! Stay w us @ Mariner's Club 606
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
732 Holiday Homes
Lowest Price
AU$322
Highest Price
AU$1,382
Popular accommodation
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal, Charming Home in Key Largo, Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities, 208 Mariners Club Key Largo | 3 Bed, 3 Bath, Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Still time for that last minute summer glow! Stay w us @ Mariner's Club 606

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 AU$322 per night from 7 Sept to 8 Sept
AU$322
7 Sept - 8 Sept
includes taxes & fees
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
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$350 per night from 17 Aug to 18 Aug
AU$350
17 Aug - 18 Aug
includes taxes & fees
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$451 per night from 20 Aug to 21 Aug
AU$451
20 Aug - 21 Aug
includes taxes & fees
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery ...
Islander 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 AU$390 per night from 7 Sept to 8 Sept
AU$390
7 Sept - 8 Sept
includes taxes & fees
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 a 2-minute drive from Florida Keys Brewing ...
Amara Cay Resort
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.