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    Check prices for these dates

    Check prices for these dates, December 15 – 16, 2026

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    Our top choices for Grassy Key condo rentals

    1. Boot Key Harbor Retreat with Pool & Breakfast

    A modern kitchen with a marble countertop, a dining area with a table set for four, and a balcony with a view of greenery.

    2. Canal Front Retreat with Pool + Free Breakfast

    A poolside area with a wooden pergola, lounge chairs, and potted plants.

    3. Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

    A poolside area with lounge chairs and umbrellas, palm trees, and a clear sky.

    4. Marina View Getaway with Pool & Free Breakfast

    A spacious living area with a large island, a sofa, and a TV mounted on the wall.

    5. Waterfront Suite with Pool, Tiki Bar & Marina

    A nighttime pool area with a clear view of the pool, lounge chairs, and palm trees.

    6. Sombrero Beach Tropical Getaway in the Heart of Marathon

    A poolside area with lounge chairs and umbrellas, palm trees, and a clear sky.

    7. Resort Condo with Marina Views, Pool, Tiki, Breakfast

    A poolside area with sun loungers and umbrellas, palm trees, and a clear blue sky.

    8. Marina View Suite with Pool & Tiki Bar

    An aerial view of a resort with a large rectangular swimming pool, multiple lounge areas with white chairs and umbrellas, and palm trees.

    9. Marina View Escape with Pool, Tiki & Breakfast

    A poolside area with lounge chairs and umbrellas, a pool, and palm trees.

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

    A dining area with a view of boats and a sunset.

    11. Waterfront Retreat with Marina Views & Pool

    A pool area with a clear blue sky, palm trees, and a covered seating area.

    12. Canalfront 1BR condo with balcony, full kitchen, Wi-Fi, parking.

    A marina with multiple boats docked, a waterfront building, and a clear sky.

    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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    Learn more about Grassy Key

    Experience the seaside area of Grassy Key—beaches, a scenic waterfront, and sights from Curry Hammock State Park to Grassy Key Marina.

    See all hotels in Grassy Key

    A building with a blue awning labeled "Dolphin Research Center" and a dolphin logo.

    Top reviews in Grassy Key

    Grassy Flats Resort & Beach Club

    A wooden deck with a pool and chairs overlooking a beach with palm trees.

    Yacht Haven Marina

    A marina with several docked boats and a row of small, white cabins with blue roofs.

    Aqua Lodge Rentals At Coconut Cay

    A beach with palm trees, a sandy path, and beach chairs.

    Seascape Resort & Marina

    A hammock on a sandy beach with palm trees, a pool, and lounge chairs in the background.

    Lime Tree Bay Resort

    Terrace/patio

    Fairfield Inn & Suites by Marriott Marathon Florida Keys

    A bar area with a long counter, bar stools, and a view of the water.

    Bonefish Bay Motel

    A wooden dock leading to a row of boats, with a thatched-roof building and palm trees in the background.

    Isla Bella Beach Resort & Spa

    An aerial view of a resort with a central pool, multiple buildings, and a beach area with sun loungers.

    Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

    A resort with a swimming pool, lounge chairs, and a view of the ocean.

    Hampton Inn Marathon - Florida Keys

    Three colorful drinks on a table with a thatched roof and outdoor seating.

    Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

    Two hammocks on a sandy beach with a clear blue sky and turquoise water.

    Captain Pips Marina & Hideaway

    A beach with a wooden pier, palm trees, and a clear blue sky.

    Knight's Key Suites

    A neatly made bed with a grey and white duvet, a wooden headboard, and a bedside table with a lamp and remote control.

    Matecumbe Resort

    A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

    Tranquility Bay Beachfront Hotel and Resort

    A swimming pool surrounded by palm trees and lounge chairs.

    Aqua Lodges at 47th Street Gulfside

    Exterior

    Gulf View Waterfront Resort

    A tropical resort with a swimming pool, palm trees, and a view of the ocean.

    Coconut Cay Resort & Marina

    A marina with a dock, a boat, and a row of buildings with large windows.

    Kingsail Resort

    A covered outdoor area with a view of a pool and palm trees.

    Frequently Asked Questions

    How much do condos in Grassy Key cost?

    The price range for condos in Grassy Key is $355 to $618 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 0.

    How many condos are there in Grassy Key?

    Pack your bags and pick from 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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