Hot Islamorada Cottage Rates

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Featured Cottages in Islamorada

RELAX in your PRIVATE Oceanfront Cottage!

RELAX in your PRIVATE Oceanfront Cottage!

Islamorada
Located in Islamorada (Matecumbe), this cottage is within a 15-minute walk of Islamorada Brewery & Distillery and History of Diving Museum.
RELAX in your PRIVATE Oceanfront Cottage!
Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise

Tavernier
Located in Tavernier (Plantation Key Colony), this cottage is within a 5-minute drive of Florida Keys Dive Center and Old Road Gallery.
Mercy’s waterfront piece of paradise
Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Key Largo
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 ...
Cottage w/ Bay View FREE Kayaks, Snorkel`
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Canal-front Florida Keys Home w/ Dock!

Canal-front Florida Keys Home w/ Dock!

3 out of 5
Tavernier
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.
Canal-front Florida Keys Home w/ Dock!
Luxury Key Largo Home w/ Guest House & Pool!

Luxury Key Largo Home w/ Guest House & Pool!

3 out of 5
Key Largo
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.
Luxury Key Largo Home w/ Guest House & Pool!
Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

Key Largo
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 ...
Kayaking, sailing, snorkeling Free w/ Cottage
Walk to Beach: Home 8 Mi to Key Largo!

Walk to Beach: Home 8 Mi to Key Largo!

3 out of 5
Tavernier
Located in Tavernier, this cottage is a 1-minute drive from Harry Harris Park and 7 minutes from Mariners Hospital.
Walk to Beach: Home 8 Mi to Key Largo!
Half-mi to Boat Ramp: Canal-front Florida Keys Gem

Half-mi to Boat Ramp: Canal-front Florida Keys Gem

3 out of 5
Tavernier
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.
Half-mi to Boat Ramp: Canal-front Florida Keys Gem
Close to Beach: Canal-front Home in Islamorada

Close to Beach: Canal-front Home in Islamorada

3 out of 5
Islamorada
Located in Islamorada (Matecumbe), this cottage is within a 5-minute drive of Sunset Drive Beach and Anne's Beach.
Close to Beach: Canal-front Home 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.

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
Highest Price
Popular accommodation
RELAX in your PRIVATE Oceanfront Cottage!, Mercy’s waterfront piece of paradise, Cottage w/ Bay View FREE Kayaks, Snorkel`, Canal-front Florida Keys Home w/ Dock!, Luxury Key Largo Home w/ Guest House & Pool!, Kayaking, sailing, snorkeling Free w/ Cottage, Walk to Beach: Home 8 Mi to Key Largo!, Half-mi to Boat Ramp: Canal-front Florida Keys Gem, Close to Beach: Canal-front Home in Islamorada

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
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
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
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

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
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
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Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
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
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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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