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

Search and Rent Grassy Key Condos

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Grassy Key condo rentals

A covered outdoor area with a table set for dining, overlooking a body of water and buildings.

1. Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Marathon
9.2 out of 10, Wonderful, (5 reviews)
"Place was perfect. Property manager was amazing and always answered questions within minutes. Definitely would stay again"
United States
lori p.
$840 nightly
The price is $933
Oct 1 - Oct 2
Total with taxes and fees
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
A covered outdoor dining area with a view of a turquoise pool and palm trees.

2. Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Marathon
10.0 out of 10, Exceptional, (166 reviews)
"Kitchen was well-equipped. Views were spectacular and the peaceful setting was everything we needed and hoped for! Would definitely consider this place for a future stay. My kids' favorite feature was the nearby Cabana Club!"
United States
Ryan K.
$975 nightly
The price is $1,081
Oct 4 - Oct 5
Total with taxes and fees
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
A modern kitchen with a marble countertop, a dining area with a table set for four, and a balcony with a view of greenery.

3. Boot Key Harbor Retreat with Pool & Breakfast

Boot Key Harbor Retreat with Pool & Breakfast
Marathon
10.0 out of 10, Exceptional, (2 reviews)
"The condo was beautifully decorated and furnished as well as being exceptionally clean."
United States
Rose P.
$333 nightly
The price is $374
Oct 1 - Oct 2
Total with taxes and fees
Boot Key Harbor Retreat with Pool & Breakfast
A poolside area with a wooden pergola, lounge chairs, and potted plants.

4. Canal Front Retreat with Pool + Free Breakfast

Canal Front Retreat with Pool + Free Breakfast
Marathon
9.8 out of 10, Exceptional, (29 reviews)
"Super easy check in, great location in the Keys and very quiet in the room."
United States
Eric
$382 nightly
The price is $429
Oct 1 - Oct 2
Total with taxes and fees
Canal Front Retreat with Pool + Free Breakfast
A nighttime pool area with a clear view of the pool, lounge chairs, and palm trees.

5. Waterfront Suite with Pool, Tiki Bar & Marina

Waterfront Suite with Pool, Tiki Bar & Marina
Marathon
10.0 out of 10, Exceptional, (1 review)
"The condo was super clean and nice very close to Publix, the beach, the flowrider! A great location along with a relaxing and beautiful place to come back to after fishing all day!"
United States
Grace K.
$337 nightly
The price is $374
Oct 1 - Oct 2
Total with taxes and fees
Waterfront Suite with Pool, Tiki Bar & Marina
A dining area with a view of boats and a sunset.

6. Waterfront Escape with Pool, Tiki, Breakfast & Marina

Waterfront Escape with Pool, Tiki, Breakfast & Marina
Marathon
10.0 out of 10, Exceptional, (2 reviews)
"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.
$343 nightly
The price is $385
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Escape with Pool, Tiki, Breakfast & Marina
A poolside area with lounge chairs and umbrellas, palm trees, and a clear sky.

7. 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, (25 reviews)
"The location and nightly entertainment. "
United States
Robert H.
$377 nightly
The price is $418
Oct 1 - Oct 2
Total with taxes and fees
Sombrero Beach Tropical Getaway in the Heart of Marathon
A spacious living area with a large island, a sofa, and a TV mounted on the wall.

8. 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
$326 nightly
The price is $366
Oct 5 - Oct 6
Total with taxes and fees
Marina View Getaway with Pool & Free Breakfast
A poolside area with lounge chairs and umbrellas, a pool, and palm trees.

9. Marina View Escape with Pool, Tiki & Breakfast

Marina View Escape with Pool, Tiki & Breakfast
Marathon
9.6 out of 10, Exceptional, (4 reviews)
"Great area"
United States
Jennifer W.
$386 nightly
The price is $433
Oct 2 - Oct 3
Total with taxes and fees
Marina View Escape with Pool, Tiki & Breakfast
A poolside area with lounge chairs and umbrellas, palm trees, and a clear sky.

10. 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, (15 reviews)
"What a charming and beautiful property. Beautiful landscape and the room was clean and comfortable. (The only minor issue was the lack of electrical outlets , but we brought our own extension cords) We definitely recommend this place 👌"
United States
JOHN
$352 nightly
The price is $390
Oct 1 - Oct 2
Total with taxes and fees
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
A pool area with a clear blue sky, palm trees, and a covered seating area.

11. Waterfront Retreat with Marina Views & Pool

Waterfront Retreat with Marina Views & Pool
Marathon
$330 nightly
The price is $370
Oct 2 - Oct 3
Total with taxes and fees
Waterfront Retreat with Marina Views & Pool
An aerial view of a resort with a large rectangular swimming pool, multiple lounge areas with white chairs and umbrellas, and palm trees.

12. Marina View Suite with Pool & Tiki Bar

Marina View Suite with Pool & Tiki Bar
Marathon
8.0 out of 10, Very good, (1 review)
"It was a little pricey but the new apartments are spotless and the bed is very confortable. Kate was fantastic to help me resolve my issue. The pool could use some renovations but it’s very clean with plenty of nice pool chairs. We will stay there again. "
United States
Florence P.
$350 nightly
The price is $393
Oct 1 - Oct 2
Total with taxes and fees
Marina View Suite with Pool & Tiki Bar
A poolside area with sun loungers and umbrellas, palm trees, and a clear blue sky.

13. 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.
$380 nightly
The price is $422
Oct 8 - Oct 9
Total with taxes and fees
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.
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Top Grassy Key Hotel Reviews

Banana Bay Resort & Marina

Banana Bay Resort & Marina

10/10 Excellent
"Staff was nice and room clean"
Alexis 3-night trip
Posted 7 hours ago
Banana Bay Resort & Marina

Find out more about Grassy Key

Grassy Key Condo Rentals information

Number of reviews
273
Accommodation
201 Condo Rentals
Lowest Price
$366
Highest Price
$1,081

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is $366 to $1,081 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 201 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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