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Our top choices for Grassy Key condo rentals

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (6 reviews)
The price is NZ$555
includes taxes & fees
6 July - 7 July
Caloosa Cove Resort by CoolVacay

Waterfront Escape with Pool, Tiki, Breakfast & Marina

Waterfront Escape with Pool, Tiki, Breakfast & Marina
Marathon
10.0 out of 10, Exceptional, (1 review)
"This is a clean, stylish condo in a location close to everything we needed, including grocery stores, restaurants, and fun things to do. It's convenient, but also feels tucked back into a private area. We enjoyed having a waterfront view. It was also nice to have access to the Skipjack resort amenities including the poolside bar and a laundry room. The included breakfast at the resort is basic, but convenient, and the staff of the resort were very welcoming and helpful. Our favorite thing about...
United States
Julie P.
The price is NZ$816
includes taxes & fees
5 July - 6 July
Waterfront Escape with Pool, Tiki, Breakfast & Marina

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
The price is NZ$785
includes taxes & fees
7 July - 8 July
Waterfront Suite with Pool, Tiki Bar & Marina

Flip-Flops & Sunshine: Islamorada Studio Escape

Flip-Flops & Sunshine: Islamorada Studio Escape
Matecumbe
10.0 out of 10, Exceptional, (6 reviews)
"Very nice clean place. Pool amazing with great views of ocean"
United States
Dawn S.
The price is NZ$639
includes taxes & fees
14 July - 15 July
Flip-Flops & Sunshine: Islamorada Studio Escape

Canal Front Retreat with Pool + Free Breakfast

Canal Front Retreat with Pool + Free Breakfast
Marathon
9.8 out of 10, Exceptional, (27 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
The price is NZ$763
includes taxes & fees
5 July - 6 July
Canal Front Retreat with Pool + Free Breakfast

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.6 out of 10, Exceptional, (23 reviews)
"Loved this place, fun atmosphere! Can’t wait to come back.. "
United States
jeff l.
The price is NZ$699
includes taxes & fees
12 July - 13 July
Sombrero Beach Tropical Getaway in the Heart of Marathon

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views
Matecumbe
9.6 out of 10, Exceptional, (15 reviews)
"We had a great stay, not only is the property and an amazing place but the staff was most accommodating and exceptional. "
United States
DAVID Y.
The price is NZ$647
includes taxes & fees
7 July - 8 July
Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Matecumbe
10.0 out of 10, Exceptional, (10 reviews)
"Old Florida vibe with modern, clean condos. Perfect location to visit the Keys. "
United States
Beckie F.
The price is NZ$798
includes taxes & fees
6 July - 7 July
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Ocean front gated privacy with 3 bedrooms and protected boat slip.

Ocean front gated privacy with 3 bedrooms and protected boat slip.
Layton
10.0 out of 10, Exceptional, (61 reviews)
"This is a beautiful place to stay for exploring the keys. We would stay here again."
United States
Mark H.
The price is NZ$1,728
includes taxes & fees
26 July - 27 July
Ocean front gated privacy with 3 bedrooms and protected boat slip.

Second Floor Ocean View Studio – Gorgeous Waterfront Escape

Second Floor Ocean View Studio – Gorgeous Waterfront Escape
Matecumbe
8.0 out of 10, Very good, (4 reviews)
"Beautiful view with great location"
United States
Doug C.
The price is NZ$644
includes taxes & fees
7 July - 8 July
Second Floor Ocean View Studio – Gorgeous Waterfront Escape

Resort Condo with Marina Views, Pool, Tiki, Breakfast

Resort Condo with Marina Views, Pool, Tiki, Breakfast
Marathon
9.4 out of 10, Exceptional, (22 reviews)
"Great place to stay which had everything we needed. Very quiet. We loved it and would stay there again!"
United States
Heather K.
The price is NZ$838
includes taxes & fees
2 July - 3 July
Resort Condo with Marina Views, Pool, Tiki, Breakfast

Anchor Here: Oceanfront 1BR Condo with Marina Access

Anchor Here: Oceanfront 1BR Condo with Marina Access
Matecumbe
9.0 out of 10, Wonderful, (8 reviews)
"Enjoyed the water and pool view "
United States
Diane Z.
The price is NZ$784
includes taxes & fees
20 July - 21 July
Anchor Here: Oceanfront 1BR Condo with Marina Access

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Marathon
9.8 out of 10, Exceptional, (11 reviews)
"Great little place. Very clean. Hot continental breakfast every day. 10/10 would go back again. Thank you! "
United States
Mandi P.
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

Tropical Tranquility: Oceanview 1BR Suite on the Island

Tropical Tranquility: Oceanview 1BR Suite on the Island
Matecumbe
9.6 out of 10, Exceptional, (20 reviews)
"Lovely property on the water with a beautiful pool."
United States
nancy d.
The price is NZ$787
includes taxes & fees
20 July - 21 July
Tropical Tranquility: Oceanview 1BR Suite on the Island

Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies

Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies
Matecumbe
10.0 out of 10, Exceptional, (5 reviews)
"Great location and wonderful views."
United States
Diane S.
The price is NZ$798
includes taxes & fees
6 July - 7 July
Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access
Matecumbe
9.6 out of 10, Exceptional, (5 reviews)
"Convenient 1br near the things we wanted to do and there are plenty of places to hang out near by when you don't want to use the pool. Recommend sombrero beach."
United States
Jon S.
The price is NZ$791
includes taxes & fees
13 July - 14 July
Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand
Matecumbe
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and very nice staff"
United States
Connie M.
The price is NZ$791
includes taxes & fees
14 July - 15 July
Stay Salty: Keys Dreams 1BR Condo Steps from the Sand

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada
Matecumbe
8.0 out of 10, Very good, (2 reviews)
"We had a wonderful stay. Beautiful view. Enjoyed the pool. Staff was very friendly and helpful. Everything was VERY CLEAN!!! Thank you very much!"
United States
Lu D.
The price is NZ$801
includes taxes & fees
6 July - 7 July
Island Time Starts Here: Cozy Ground Floor Suite in Islamorada
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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Top Grassy Key Hotel Reviews

Find out more about Grassy Key

Grassy Key Condo Rentals information

Number of reviews
215
Accommodation
184 Condo Rentals
Lowest Price
NZ$555
Highest Price
NZ$1,728

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is NZ$555 to NZ$1,728 per night. No matter your budget, you're sure to find someplace that suits your needs — as well as your entire squad! 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.
How many condos are there in Grassy Key?
Pack your bags and pick from 184 condos in Grassy Key. For work-related travel, a family getaway or anything in between, Expedia will help you find the right place in a few easy clicks.

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