A dolphin swimming near a wooden dock and a tree branch in the water.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Grassy Key condo rentals

Exterior

Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay
3.0 star property
Matecumbe
9.8 out of 10, Exceptional, (6 reviews)
"Easy check in if you come After business hours. Kayaks and sport equipment available. Has a small beach which is unique to the Keys. Pool pretty much vacant at all times. Great views. Highly recommend."
United States
Dana
The price is AED 918
AED 1,157 total
includes taxes & fees
6 Jul - 7 Jul
Caloosa Cove Resort by CoolVacay
Interior

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 AED 789
AED 1,683 total
includes taxes & fees
5 Jul - 6 Jul
Waterfront Escape with Pool, Tiki, Breakfast & Marina
Outdoor pool

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
The price is AED 730
AED 1,608 total
includes taxes & fees
7 Jul - 8 Jul
Waterfront Suite with Pool, Tiki Bar & Marina
Pool

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 AED 970
AED 1,288 total
includes taxes & fees
6 Jul - 7 Jul
Flip-Flops & Sunshine: Islamorada Studio Escape
Outdoor pool, a heated pool

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 AED 591
AED 1,580 total
includes taxes & fees
5 Jul - 6 Jul
Canal Front Retreat with Pool + Free Breakfast
Terrace/patio

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 AED 601
AED 1,447 total
includes taxes & fees
12 Jul - 13 Jul
Sombrero Beach Tropical Getaway in the Heart of Marathon
Pool

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 AED 970
AED 1,365 total
includes taxes & fees
7 Jul - 8 Jul
Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views
Pool

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 AED 1,205
AED 1,667 total
includes taxes & fees
6 Jul - 7 Jul
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
Property grounds

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 AED 1,800
AED 3,679 total
includes taxes & fees
26 Jul - 27 Jul
Ocean front gated privacy with 3 bedrooms and protected boat slip.
Property grounds

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.
Second Floor Ocean View Studio – Gorgeous Waterfront Escape
Outdoor pool, a heated pool

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 AED 710
AED 1,735 total
includes taxes & fees
2 Jul - 3 Jul
Resort Condo with Marina Views, Pool, Tiki, Breakfast
Exterior

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.
Anchor Here: Oceanfront 1BR Condo with Marina Access
Terrace/patio

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.
The price is AED 612
AED 1,447 total
includes taxes & fees
3 Jul - 4 Jul
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
Outdoor dining

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.
Tropical Tranquility: Oceanview 1BR Suite on the Island
Exterior

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.
Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies
Pool

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 AED 1,205
AED 1,659 total
includes taxes & fees
13 Jul - 14 Jul
Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access
Exterior

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 AED 1,205
AED 1,659 total
includes taxes & fees
14 Jul - 15 Jul
Stay Salty: Keys Dreams 1BR Condo Steps from the Sand
Exterior

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.
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

Hampton Inn Marathon - Florida Keys

Hampton Inn Marathon - Florida Keys

10/10 Excellent
"Location! Location! Location! Sunsets in the park across the street are amazing. 2nd fl balcony was perfect. Beautiful lush property. Room was spacious, new and spotless. Great shower. Comfortable bed. Loved the padded chair and small table. Room service with nice menu. GREAT Breakfast. And the pool area and tiki bar. What’s not to love? Will stay here every time I am in The Keys."
Barbara 2-night trip
Posted 1 hour ago
Hampton Inn Marathon - Florida Keys

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is AED 1,157 to AED 3,679 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.
What are the best condos in Grassy Key?
A traveler favorite is The Reef At Marathon. Settle in at this 3-star property which offers a tennis court and a swimming pool. Indigo Reef Resort Villas And Marina By Keyscaribbean is another highly rated condo to consider. Spend your break at this popular 3.5-star option and make the most of conveniences like a swimming pool and a barbecue grill. You'll have your pick of multiple condos in Grassy Key with a total average guest review rating of 9.5.
How many condos are there in Grassy Key?
Pack your bags and pick from 183 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.
Why book your condo in Grassy Key with Expedia?
Getaways shouldn't be difficult, so if you're seeking condos at an affordable rate, Expedia has your back. Keep costs down and pick something small and cozy, or splurge on a high-end condo and really spoil your crew. Our search filters make it easy to lock in a stay in Grassy Key that meets your needs.
How can I find cheap condos in Grassy Key?
With Expedia's filter tool, getting your hands on cheap condos in Grassy Key is easy. To view accommodations that'll make your wallet smile, fine-tune your search results by star rating, budget and amenities.