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Compare 29 Cottages in Islamorada with updated reviews, rates, and availability.

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (103)
"Our third time staying here was as wonderful as the first two. So peaceful and comfortable. All the comforts of home, close to grocery, restaurants and pharmacy if needed. It’s just the best place to stay when escaping the northern states for a little warmth and sunshine in mid winter. I can’t imagine staying anywhere else in the Keys.This place is our favorite of favorites!"
RELAX in your PRIVATE Oceanfront Cottage!

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage

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

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

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat

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

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

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Cosy Cottage in Islamorada with private garden & pool - 6 pers.

Key Largo Cottages w/ Free Sailboat, Kayaks + More

Key Largo Cottages w/ Free Sailboat, Kayaks + More

Waterfront Cottage at Tavernier, Florida Keys

10.0 out of 10, Exceptional, (3)
"My wife and I had a wonderful stay here during the month of March escaping the cold from the Northeast. The house was immaculate and decorated very nicely inside. The kitchen and bathrooms were well stocked with essentials items. The neighborhood was very peaceful and quiet and the neighbors were very friendly. The house backs up to a canal/waterway from which we could watch the graceful pelicans gliding by from the very large back deck which is where we spent a lot of our time. Rene was a...
Waterfront Cottage at Tavernier, Florida Keys

Florida Keys Waterfront with Boat Dock

2.0 star property
Florida Keys Waterfront with Boat Dock

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

Charming Seaside Getaway with All the Comforts of Home

Charming Seaside Getaway with All the Comforts of Home

Lush tropical plantings in a gated compound located directly on the Florida Bay

Lush tropical plantings in a gated compound located directly on the Florida Bay

Walk to Beach: Home 8 Mi to Key Largo!

3.0 star property
Walk to Beach: Home 8 Mi to Key Largo!

Luxury Key Largo Home w/ Guest House & Pool!

3.0 star property
Luxury Key Largo Home w/ Guest House & Pool!
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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Other property types in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (428)
"Quaint, clean, friendly staff! "
The price is AED 854
AED 1,152 total
includes taxes & fees
16 Apr - 17 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (53)
"Above and beyond service. "
The price is AED 2,127
AED 2,595 total
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

9.8 out of 10, Exceptional, (79)
"Three generations of our family enjoyed a wonderful vacation at The Last Resort. The house was beautifully appointed and well stocked as described in the listing. It had everything we needed for a memorable beach vacation. The owner was friendly, helpful, and easy to communicate with. We hope to return! back!ThownerfrieThowwith. "
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25
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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