Hot Islamorada Cottage Rates

Start date: Check-in selected.
To Date
End date: Check-out

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 Cottages in Islamorada

Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach

Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach

Key Largo FL
With a stay at this cottage in Key Largo, you'll be within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
Opens in a new windowBayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Located in Islamorada (Matecumbe), this cottage is within a 15-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.
Opens in a new windowOceanfront Private Cottage!
Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Key Largo FL
With a stay at this cottage in Key Largo, you'll be on the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowCottage w/ Bay View FREE Kayaks, Snorkel`
Save an average of 15% on thousands of hotels when you're signed in
Luxury Key Largo Home w/ Guest House & Pool!

Luxury Key Largo Home w/ Guest House & Pool!

3 out of 5
Key Largo FL
With a stay at this cottage in Key Largo (Buccaneer Point), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and North Nest Key.
Opens in a new windowLuxury Key Largo Home w/ Guest House & Pool!
Waterfront Gem w/ Decks, Views & More in Key Largo

Waterfront Gem w/ Decks, Views & More in Key Largo

3 out of 5
Key Largo FL
With a stay at this cottage in Key Largo (Buccaneer Point), you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and North Nest Key.
Opens in a new windowWaterfront Gem w/ Decks, Views & More in Key Largo
Canal-front Florida Keys Home w/ Dock!

Canal-front Florida Keys Home w/ Dock!

3 out of 5
Tavernier FL
With a stay at this cottage in Tavernier, you'll be within a 5-minute drive of Florida Keys Dive Center and Old Road Gallery.
Opens in a new windowCanal-front Florida Keys Home w/ Dock!
Spacious Canal-front Home: Florida Keys Gem

Spacious Canal-front Home: Florida Keys Gem

3 out of 5
Tavernier FL
With a stay at this cottage in Tavernier (Indian Waterways), you'll be within a 5-minute drive of Old Road Gallery and Florida Keys Dive Center.
Opens in a new windowSpacious Canal-front Home: Florida Keys Gem
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

3 out of 5
Key Largo FL
With a stay at this cottage in Key Largo, you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
Opens in a new window1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Key Largo FL
With a stay at this cottage in Key Largo, you'll be near the beach, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's Big ...
Opens in a new windowCottage w/ FREE Sailboat, Kayak, Bikes & More
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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Islamorada will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Islamorada definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Islamorada, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Islamorada Cottages essential information

Accommodation
32 Cottages
Lowest Price
AU$505
Highest Price
AU$845
Popular accommodation
Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach, Oceanfront Private Cottage!, Cottage w/ Bay View FREE Kayaks, Snorkel`, Luxury Key Largo Home w/ Guest House & Pool!, Waterfront Gem w/ Decks, Views & More in Key Largo, Canal-front Florida Keys Home w/ Dock!, Spacious Canal-front Home: Florida Keys Gem, 1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!, Cottage w/ FREE Sailboat, Kayak, Bikes & More

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$629 per night from 8 Feb to 9 Feb
AU$629
8 Feb - 9 Feb
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 ...
Opens in a new windowChesapeake Beach 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 AU$746 per night from 10 Feb to 11 Feb
AU$746
10 Feb - 11 Feb
includes taxes & fees
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be steps from Matecumbe United Methodist Church and 5 minutes by foot from Florida Keys Brewing ...
Opens in a new windowCheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is AU$505 per night from 8 Feb to 9 Feb
AU$505
8 Feb - 9 Feb
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 ...
Opens in a new windowAmara Cay Resort
Save an average of 15% on thousands of hotels when you're signed in
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 AU$845 per night from 16 Feb to 17 Feb
AU$845
16 Feb - 17 Feb
includes taxes & fees
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil ...
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
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.