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Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Cottages in Grassy Key and around

Tropical Cottages
Relax in a serene outdoor space surrounded by lush greenery, featuring a thatched-roof structure and comfortable wicker seating.

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (824)
"Cute place, convenient location"
The price is €106
includes taxes & fees
13 Jul - 14 Jul
Tropical Cottages
Keys Waterfront Half-Duplex, Ocean side 37' Dock,
Guests can enjoy stunning sea views from the pool area, which offers lounge chairs and a dock with boats.

Keys Waterfront Half-Duplex, Ocean side 37' Dock,

10.0 out of 10, Exceptional, (104)
"Property was just right for us, nice location, on canal, close by restaurants, kayak, bikes provided, nice pool, excellent."
Keys Waterfront Half-Duplex, Ocean side 37' Dock,
Brand new 5bed/6bath pool w/45 foot dockage - available with 2 more homes
Relax by the serene pool surrounded by lush greenery and a brick wall, with comfortable lounge chairs and a small table.

Brand new 5bed/6bath pool w/45 foot dockage - available with 2 more homes

10.0 out of 10, Exceptional, (3)
"The property was clean and well kept. The amenities were great, pool, dock, hot tub, fishing from the dock. We had 5 adult couples in our group And the accommodations were fabulous. The house is beautiful!Thank youJessi and Debbie"
Brand new 5bed/6bath pool w/45 foot dockage - available with 2 more homes
Pet Friendly Half-Duplex Cottage with kayaks and 40' Slip Option at Marina
Relax on the shaded patio with a table and chairs, and enjoy outdoor dining or relaxation.

Pet Friendly Half-Duplex Cottage with kayaks and 40' Slip Option at Marina

9.2 out of 10, Wonderful, (5)
"Central to all keys making it easy to see it all. Comfortable little home with everything you need in the kitchen."
Pet Friendly Half-Duplex Cottage with kayaks and 40' Slip Option at Marina
Waterfront Key Colony Beach Home w/ Golf Cart!
Relax by the pool surrounded by comfortable lounge chairs and shaded by umbrellas.

Waterfront Key Colony Beach Home w/ Golf Cart!

3.0 star property
Waterfront Key Colony Beach Home w/ Golf Cart!
Brand new 5bed/6Bth pool w/76 ft of Dockage- 2 Homes Next Door Available as well
Relax by the serene pool, surrounded by lush greenery and a tranquil body of water.

Brand new 5bed/6Bth pool w/76 ft of Dockage- 2 Homes Next Door Available as well

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay in this beautiful home. From the moment we put the key in the door we were blown away with the wonderful view. For over forty years we have visited Florida and this is the first house we have stayed in where I could say that I honestly couldn’t think of a thing to improve it, all of us immediately felt at home as it was all the little details that made it. We were visited by manatee and iguana and to see different fish in their natural environment was a bonus. We want...
Brand new 5bed/6Bth pool w/76 ft of Dockage- 2 Homes Next Door Available as well
Beachy getaway with pool, water views, furnished patio, & dock access
Enjoy breathtaking views of the water from your balcony.

Beachy getaway with pool, water views, furnished patio, & dock access

9.4 out of 10, Exceptional, (33)
"Great time! "
Beachy getaway with pool, water views, furnished patio, & dock access
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Relax by the pool surrounded by lush surroundings and lounge in style with comfortable seating.

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Instant open water access! Private beach, dock. Rates start at 1995 inquire
Relax in this stylish room with a large dining table, unique ceiling fan, and a sofa area.

Instant open water access! Private beach, dock. Rates start at 1995 inquire

Instant open water access! Private beach, dock. Rates start at 1995 inquire
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
Guests can enjoy a tranquil marina experience with a wooden pier leading to a dock area.

BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!

10.0 out of 10, Exceptional, (2)
"We had an awesome time! The house was perfect for us and the host is fantastic! Loved the community and amenities! We would definitely stay again "
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
Marathon Vacation Rental With Pool Access!
Relax on the shaded deck overlooking the pool, surrounded by natural ambiance and comfortable seating.

Marathon Vacation Rental With Pool Access!

3.0 star property
Marathon Vacation Rental With Pool Access!
Close to Beach: Canal-front Home in Islamorada
Enjoy a tranquil beach experience with a picturesque pier and calm waters.

Close to Beach: Canal-front Home in Islamorada

3.0 star property
Close to Beach: Canal-front Home in Islamorada
Soothing Duck Key Vacation Rental!
Relax in a shaded patio area with a thatched roof, surrounded by lush greenery and a nearby pool.

Soothing Duck Key Vacation Rental!

3.0 star property
Soothing Duck Key Vacation Rental!
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Relax by the pool surrounded by lounge chairs and umbrellas, with steps leading down to the water.

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!

Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
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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Frequently asked questions

How much do cottages in Grassy Key cost?
Prices for cottages in Grassy Key range between €106 and €106 per night. No matter your budget, you'll find an ideal place to touch base with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly cottages in Grassy Key?
Book in to Tropical Cottages and make your family trip to Grassy Key the best one yet. This family-friendly cottage has a 3-star rating and amenities such as housekeeping services and a picnic area. Once you've checked in and unpacked your suitcase, there's a host of family-friendly attractions to visit around Grassy Key. Coco Plum Beach and Crane Point Museum and Nature Centre are two of our top picks.
Why book your cottage in Grassy Key with Expedia?
Reserving a cottage in Grassy Key is as easy as working out your travel dates and choosing your ideal place for a holiday in the outdoors. From upmarket retreats to inexpensive properties and cottages that feature perks like free WiFi, Expedia has something for all traveller tastes. As for the best deals around? We have them too!