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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

RELAX in your PRIVATE Oceanfront Cottage!
Lake

RELAX in your PRIVATE Oceanfront Cottage!

10.0 out of 10, Exceptional, (106)
"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
Outdoor pool

Mercy’s waterfront piece of paradise

Mercy’s waterfront piece of paradise
Cottage w/ Bay View FREE Kayaks, Snorkel`
Marina

Cottage w/ Bay View FREE Kayaks, Snorkel`

Cottage w/ Bay View FREE Kayaks, Snorkel`
Kayaking, sailing, snorkeling Free w/ Cottage
Marina

Kayaking, sailing, snorkeling Free w/ Cottage

Kayaking, sailing, snorkeling Free w/ Cottage
Cottage w/ FREE Sailboat, Kayak, Bikes & More
Marina

Cottage w/ FREE Sailboat, Kayak, Bikes & More

Cottage w/ FREE Sailboat, Kayak, Bikes & More
Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Marina

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

Large House w/ FREE Sailboat, Kayaks, Snorkel and Fishing Gear
Bayside view Cottage , Free kayaks and sailboat
Marina

Bayside view Cottage , Free kayaks and sailboat

Bayside view Cottage , Free kayaks and sailboat
Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Marina

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use

Bungalow w/ FREE Kayaks, Sailboat, Bicycle Use
Free sailing, kayaking, water toys etc w/ Cottage
Marina

Free sailing, kayaking, water toys etc w/ Cottage

Free sailing, kayaking, water toys etc w/ Cottage
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
Pool

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
Marina

Key Largo Cottages w/ Free Sailboat, Kayaks + More

Key Largo Cottages w/ Free Sailboat, Kayaks + More
1 Mi to Dtwn: Oceanfront Gem w/ Resort Amenities!
Interior

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
Marina

Cottage w/ Full Kitchen FREE sailboats and kayaks

Cottage w/ Full Kitchen FREE sailboats and kayaks
Charming Seaside Getaway with All the Comforts of Home
Terrace/patio

Charming Seaside Getaway with All the Comforts of Home

Charming Seaside Getaway with All the Comforts of Home
Waterfront Cottage at Tavernier, Florida Keys
Fridge, microwave, oven, stovetop

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
Miscellaneous

Florida Keys Waterfront with Boat Dock

2.0 star property
Florida Keys Waterfront with Boat Dock
Cottage w/ Private Yard, Free Kayaks, Boats, Etc
Marina

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

Cottage w/ Private Yard, Free Kayaks, Boats, Etc
Luxury Key Largo Home w/ Guest House & Pool!
Interior

Luxury Key Largo Home w/ Guest House & Pool!

3.0 star property
Luxury Key Largo Home w/ Guest House & Pool!
Walk to Beach: Home 8 Mi to Key Largo!
Interior

Walk to Beach: Home 8 Mi to Key Largo!

3.0 star property
Walk to Beach: Home 8 Mi to Key Largo!
Canal-front Florida Keys Home w/ Dock!
House (2 Bedrooms) | Interior

Canal-front Florida Keys Home w/ Dock!

3.0 star property
Canal-front Florida Keys Home w/ Dock!
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
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (466)
"Great place !"
The price is AED 407
AED 648 total
includes taxes & fees
21 May - 22 May
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (59)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AED 1,958
AED 2,405 total
includes taxes & fees
2 Jun - 3 Jun
The Islands of Islamorada
Beach Residence / Private overwater dock / Heated Pool / Mahi Key
Miscellaneous

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

Beach Residence / Private overwater dock / Heated Pool / Mahi Key
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.