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Search and Rent Grassy Key Condos

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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)
"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
$290 nightly
The price is $326
Jul 14 - Jul 15
Total with taxes and fees
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.
$414 nightly
The price is $458
Jul 5 - Jul 6
Total with taxes and fees
Waterfront Escape with Pool, Tiki, Breakfast & Marina

Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
$392 nightly
The price is $434
Jul 7 - Jul 8
Total with taxes and fees
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.
$321 nightly
The price is $358
Jul 6 - Jul 7
Total with taxes and fees
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
$382 nightly
The price is $424
Jul 6 - Jul 7
Total with taxes and fees
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.
$355 nightly
The price is $394
Jul 12 - Jul 13
Total with taxes and fees
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.
$335 nightly
The price is $372
Jul 7 - Jul 8
Total with taxes and fees
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.
$409 nightly
The price is $454
Jul 6 - Jul 7
Total with taxes and fees
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.
$903 nightly
The price is $1,002
Jul 26 - Jul 27
Total with taxes and fees
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.
$321 nightly
The price is $358
Jul 6 - Jul 7
Total with taxes and fees
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.
$414 nightly
The price is $459
Jul 2 - Jul 3
Total with taxes and fees
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.
$407 nightly
The price is $452
Jul 20 - Jul 21
Total with taxes and fees
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.
$348 nightly
The price is $387
Jul 27 - Jul 28
Total with taxes and fees
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.
$407 nightly
The price is $452
Jul 20 - Jul 21
Total with taxes and fees
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.
$409 nightly
The price is $454
Jul 6 - Jul 7
Total with taxes and fees
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.
$407 nightly
The price is $452
Jul 13 - Jul 14
Total with taxes and fees
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.
$409 nightly
The price is $454
Jul 6 - Jul 7
Total with taxes and fees
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.
$409 nightly
The price is $454
Jul 6 - Jul 7
Total with taxes and fees
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
6
Accommodation
183 Condo Rentals
Lowest Price
$326
Highest Price
$326

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is $326 to $326 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 9.8.
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.
Are there any family-friendly condos in Grassy Key?
Many visitors needing family-friendly condos in Grassy Key pick The Reef At Marathon. With a 3-star rating and amenities like an ocean view and a marina, you're sure to feel right at home here. Alternatively, check out 3.5-star Indigo Reef Resort Villas And Marina By Keyscaribbean. A marina and a terrace help make it a comfortable base for your Grassy Key getaway. After checking in and chilling in your comfy new digs, it's time to head out and visit some of the local sights. Coco Plum Beach and Curry Hammock State Park are some of the best family-friendly attractions in Grassy Key.
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.

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