Hot Islamorada Cottage Rates

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

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Key Largo
When you stay at this cottage in Key Largo, you'll be on the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral Reef ...
Cottage w/ Bay View FREE Kayaks, Snorkel`
Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise

Tavernier
With a stay at this cottage in Tavernier (Plantation Key Colony), you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and Florida Keys Dive ...
Mercy’s waterfront piece of paradise
Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Kayaking, sailing, snorkeling Free w/ Cottage
Save an average of 15% on thousands of hotels when you're signed in
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

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

3 out of 5
Key Largo
With a stay at this cottage in Key Largo, you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Free sailing, kayaking, water toys etc w/ Cottage
Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Cottage w/ FREE Sailboat, Kayak, Bikes & More
Key Largo Cottages w/ Free Sailboat, Kayaks + More

Key Largo Cottages w/ Free Sailboat, Kayaks + More

Key Largo
When you stay at this cottage in Key Largo, you'll be near the beach, a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral ...
Key Largo Cottages w/ Free Sailboat, Kayaks + More
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Key Largo
With a stay at this cottage in Key Largo, you'll be a 1-minute drive from Jimmy Johnson's Big Chill and 8 minutes from John Pennekamp Coral Reef State Park.
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
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
25 Cottages
Lowest Price
AU$668
Highest Price
AU$830
Popular accommodation
Cottage w/ Bay View FREE Kayaks, Snorkel`, Mercy’s waterfront piece of paradise, Kayaking, sailing, snorkeling Free w/ Cottage, 1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!, Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear, Free sailing, kayaking, water toys etc w/ Cottage, Cottage w/ FREE Sailboat, Kayak, Bikes & More, Key Largo Cottages w/ Free Sailboat, Kayaks + More, Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Top trending hotels in Islamorada

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$689 per night from 11 Feb to 12 Feb
AU$689
includes taxes & fees
11 Feb - 12 Feb
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
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$830 per night from 6 Feb to 7 Feb
AU$830
includes taxes & fees
6 Feb - 7 Feb
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
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$668 per night from 4 Feb to 5 Feb
AU$668
includes taxes & fees
4 Feb - 5 Feb
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
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$693 per night from 9 Feb to 10 Feb
AU$693
includes taxes & fees
9 Feb - 10 Feb
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
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.