Hot Islamorada Cottage Rates

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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
Stay at this cottage in Key Largo. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions John Pennekamp Coral Reef State Park and Jimmy Johnson's ...
Opens in a new windowBayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach
Oceanfront Private Cottage!

Oceanfront Private Cottage!

Islamorada FL
Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Islamorada Brewery ...
Opens in a new windowOceanfront Private Cottage!
Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Key Largo FL
Stay at this beach cottage in Key Largo. Enjoy a beach locale, laundry facilities and cable/satellite TV service. Popular attractions John Pennekamp Coral Reef ...
Opens in a new windowCottage w/ Bay View FREE Kayaks, Snorkel`
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Luxury Key Largo Home w/ Guest House & Pool!

Luxury Key Largo Home w/ Guest House & Pool!

3 out of 5
Key Largo FL
Stay at this cottage in Key Largo. Enjoy free parking, balconies and an in-room coffee maker. Popular attractions John Pennekamp Coral Reef State Park and Jimmy ...
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
Stay at this cottage in Key Largo. Enjoy patios and air conditioning. Popular attractions John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill ...
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
Stay at this cottage in Tavernier. Enjoy free parking, balconies and air conditioning. Popular attractions Florida Keys Dive Center and Mangrove Marina are located ...
Opens in a new windowCanal-front Florida Keys Home w/ Dock!
Close to Beach: Canal-front Home in Islamorada

Close to Beach: Canal-front Home in Islamorada

3 out of 5
Islamorada FL
Stay at this 3-star cottage in Islamorada. Enjoy free parking, patios and air conditioning. Popular attractions Sunset Drive Beach and Anne's Beach are located ...
Opens in a new windowClose to Beach: Canal-front Home in Islamorada
Spacious Canal-front Home: Florida Keys Gem

Spacious Canal-front Home: Florida Keys Gem

3 out of 5
Tavernier FL
Stay at this cottage in Tavernier. Enjoy free parking, balconies and air conditioning. Popular attractions Old Road Gallery and Florida Keys Dive Center are ...
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
Stay at this cottage in Key Largo. Enjoy free parking, a garden and balconies. Popular attractions John Pennekamp Coral Reef State Park and Jacob's Aquatic Center ...
Opens in a new window1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
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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
NZ$461
Highest Price
NZ$735
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!, Close to Beach: Canal-front Home in Islamorada, Spacious Canal-front Home: Florida Keys Gem, 1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!

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 NZ$461 per night from 25 Jan to 26 Jan
NZ$461
25 Jan - 26 Jan 2026
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowChesapeake Beach Resort
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 NZ$735 per night from 4 Jan to 5 Jan
NZ$735
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy free Wi-Fi, 3 outdoor pools and 4 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 NZ$568 per night from 4 Jan to 5 Jan
NZ$568
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowAmara Cay Resort
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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 NZ$702 per night from 4 Jan to 5 Jan
NZ$702
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
Opens in a new windowCheeca Lodge & Spa
Don't see what you're looking for?
See all available properties 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.

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^Subject to availability and chosen travel dates.