Search Condo Rentals in Grassy Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 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
9.6 out of 10, Exceptional, (5 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 SAR 606
SAR 809 total
includes taxes & fees
23 Jun - 24 Jun
Caloosa Cove Resort by CoolVacay
Smart TV, table tennis

Marina View Getaway with Pool & Free Breakfast

Marina View Getaway with Pool & Free Breakfast
Marathon
10.0 out of 10, Exceptional, (1 review)
"Very clean and convenient to shops and restaurants "
United States
JOHN
The price is SAR 799
SAR 1,703 total
includes taxes & fees
23 Jun - 24 Jun
Marina View Getaway with Pool & Free Breakfast
Outdoor pool

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
The price is SAR 649
SAR 1,518 total
includes taxes & fees
23 Jun - 24 Jun
Waterfront Suite with Pool, Tiki Bar & Marina
Terrace/patio

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.8 out of 10, Exceptional, (22 reviews)
"Loved this place, fun atmosphere! Can’t wait to come back.. "
United States
jeff l.
The price is SAR 682
SAR 1,555 total
includes taxes & fees
16 Jul - 17 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 SAR 634
SAR 915 total
includes taxes & fees
25 Jun - 26 Jun
Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views
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 SAR 645
SAR 1,675 total
includes taxes & fees
21 Jun - 22 Jun
Canal Front Retreat with Pool + Free Breakfast
Outdoor pool

Marina View Escape with Pool, Tiki & Breakfast

Marina View Escape with Pool, Tiki & Breakfast
Marathon
10.0 out of 10, Exceptional, (3 reviews)
"Great area"
United States
Jennifer W.
The price is SAR 681
SAR 1,570 total
includes taxes & fees
21 Jun - 22 Jun
Marina View Escape with Pool, Tiki & Breakfast
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 SAR 835
SAR 1,763 total
includes taxes & fees
21 Jun - 22 Jun
Waterfront Escape with Pool, Tiki, Breakfast & Marina
Outdoor pool

Waterfront Retreat with Marina Views & Pool

Waterfront Retreat with Marina Views & Pool
Marathon
The price is SAR 786
SAR 1,708 total
includes taxes & fees
24 Jun - 25 Jun
Waterfront Retreat with Marina Views & Pool
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 SAR 634
SAR 915 total
includes taxes & fees
25 Jun - 26 Jun
Flip-Flops & Sunshine: Islamorada Studio Escape
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 SAR 950
SAR 1,304 total
includes taxes & fees
24 Jun - 25 Jun
Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access
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.
The price is SAR 950
SAR 1,304 total
includes taxes & fees
23 Jun - 24 Jun
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
9.6 out of 10, Exceptional, (9 reviews)
"Great"
United States
John M.
The price is SAR 591
SAR 1,434 total
includes taxes & fees
29 Jun - 30 Jun
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
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.
The price is SAR 950
SAR 1,330 total
includes taxes & fees
28 Jun - 29 Jun
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 SAR 950
SAR 1,304 total
includes taxes & fees
23 Jun - 24 Jun
Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access
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.
The price is SAR 950
SAR 1,304 total
includes taxes & fees
23 Jun - 24 Jun
Island Time Starts Here: Cozy Ground Floor Suite in Islamorada
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.
The price is SAR 1,032
SAR 1,453 total
includes taxes & fees
29 Jun - 30 Jun
Tropical Tranquility: Oceanview 1BR Suite on the Island
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 SAR 950
SAR 1,330 total
includes taxes & fees
28 Jun - 29 Jun
Stay Salty: Keys Dreams 1BR Condo Steps from the Sand
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 SAR 563
SAR 1,557 total
includes taxes & fees
23 Jun - 24 Jun
Resort Condo with Marina Views, Pool, Tiki, Breakfast
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Grassy Key Hotel Reviews

Skipjack Resort & Marina

Skipjack Resort & Marina

10/10 Excellent
"We stayed one night at Skipjack Resort & Marina while making our way through the Florida Keys toward Key West, and it was a great overnight stop. The resort is clean and comfortable, with a nice pool area and beautiful marina views. While the waterfront view is of the marina rather than the open ocean, it still provides a relaxing Florida Keys atmosphere. One of the biggest highlights of our stay was the front desk hostess at check-in. She was absolutely fantastic friendly, thorough, and took the time to explain everything about the property and local area. Excellent customer service and a wonderful first impression. The resort also offers free breakfast and free parking, which were appreciated perks during our trip. It isn’t a luxury resort, but it doesn’t try to be. It’s a comfortable, convenient, and affordable place to stay with everything you need. The location is excellent, close to restaurants, bars, and local attractions such as the Turtle Hospital. It’s also a perfect stopping point before crossing the Seven Mile Bridge on the way to Key West. Overall, Skipjack is a great no-frills option in Marathon. Comfortable accommodations, friendly staff, good amenities, and a convenient location make it an ideal overnight stop while exploring the Keys."
Trici 1-night trip
Posted 1 hour ago
Skipjack Resort & Marina

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is SAR 809 to SAR 809 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 9.6.
How many condos are there in Grassy Key?
Pack your bags and pick from 185 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.