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Featured Condo Rentals in Grassy Key

Indigo Reef Resort Villas & Marina by KeysCaribbean

3.5 star property
9.2 out of 10, Wonderful, (49)
"A real gem. This property is clean and beautiful. Brand new dock, landscaping is perfect, location is within minutes of everything you would want while maintaining a “getting away from it all” vibe. We will be back. "
Indigo Reef Resort Villas & Marina by KeysCaribbean

Sombrero Beach Tropical Getaway in the Heart of Marathon

2.0 star property
10.0 out of 10, Exceptional, (6)
"this place was great . the owner was super nice and handled a small problem fast. as for location it was also great. close to beach. and resturants. we traveled to key west one day and had a blast..."
The price is AU$593
includes taxes & fees
26 July - 27 July
Sombrero Beach Tropical Getaway in the Heart of Marathon

Canal-front condo with amazing views & convenient location

8.6 out of 10, Excellent, (42)
"Atmosphere around the condos was awesome. Condo was exactly what was needed after long days on the water"
Canal-front condo with amazing views & convenient location

The Reef at Marathon

3.0 star property
9.2 out of 10, Wonderful, (129)
"Excellent location, well maintained!"
The Reef at Marathon

One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!

10.0 out of 10, Exceptional, (200)
"Very nice property with a beach. Very helpful owner. Near the center of the Keys and accessible to everything. "
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!

Luxury 3BR/3BA Cottage with the Best Sunset Views in the Florida Keys!

10.0 out of 10, Exceptional, (201)
"The property description failed to mention that the cabana club is 10 miles away."
Luxury 3BR/3BA Cottage with the Best Sunset Views in the Florida Keys!

Private Beach steps from condo-no stairs-king size bed-fast wifi-it's loaded.

10.0 out of 10, Exceptional, (78)
"Everything was great. "
Private Beach steps from condo-no stairs-king size bed-fast wifi-it's loaded.

Tropical oasis near all the action with central AC & balcony

8.8 out of 10, Excellent, (37)
"Just a weekend getaway, to relax and recharge, this villa was perfect in the perfect place. "
Tropical oasis near all the action with central AC & balcony

Florida Keys Spacious 1 BR with 2 Balconies Pool view

10.0 out of 10, Exceptional, (6)
"Caloosa Cove resort in Islamorada was perfect! Lodging was perfect for 2. Pool and pool area was quite relaxing, yet refreshing. It was nice to have the waterfront beach also to relax, kayak or paddle board. Location in Islamorada is perfect. Being in the center of keys allowed us to venture both ways for sightseeing and restaurants. "
Florida Keys Spacious 1 BR with 2 Balconies Pool view

Waters Edge: 2 BR, 2.5 BA Condominium in Marathon, Sleeps 4

10.0 out of 10, Exceptional, (6)
"Great getaway for some great warm weather. Very relaxing. "
Waters Edge: 2 BR, 2.5 BA Condominium in Marathon, Sleeps 4

Vibrant, waterfront retreat with WiFi, balcony & dock access

8.2 out of 10, Very good, (15)
"Great place "
Vibrant, waterfront retreat with WiFi, balcony & dock access

Private Tropical Beach-White Sand, Crystal Clear water! Pool WIFI It's Loaded!

9.8 out of 10, Exceptional, (134)
"Very beautiful views of ocean and pool. Very close to all activities, shopping, grocery shopping, restaurants, and beaches. 45 minutes from Key West. Condo spacious and comfortable. Mike very responsive to all our questions."
Private Tropical Beach-White Sand, Crystal Clear water! Pool WIFI It's Loaded!

BEACHFRONT CONDO on Coco Plum Beach with Heated Pool

9.8 out of 10, Exceptional, (56)
"This property is the perfect place for a Keys getaway. The condo has everything you need, its clean, has a great beach and pool and is central to all the attractions of the Keys. We are definitely going to be coming back! "
BEACHFRONT CONDO on Coco Plum Beach with Heated Pool

Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC

10.0 out of 10, Exceptional, (2)
"Great place"
Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC

AQUAMARINE OCEANVIEW “FLASH SALE 5/1-5/10/25+DOCK+POOL+GYM+”150” 5 STAR REVIEWS!

10.0 out of 10, Exceptional, (153)
"Great location—quiet but close to everything. Loved having a dock right out the back door. Will definitely be back"
AQUAMARINE OCEANVIEW “FLASH SALE 5/1-5/10/25+DOCK+POOL+GYM+”150” 5 STAR REVIEWS!

KCB-access Private Cabana Club,Dock on Canal,PET Friendly, Pickle ball courts

9.4 out of 10, Exceptional, (60)
"We really enjoyed our trip and would stay again. This duplex is on a quiet street a short walk from a membership club right on the beach with a bar, pool and hot tub. It is the best of both worlds, getting a quiet roomy place to stay then head over to the Cabana Club for some beach time."
KCB-access Private Cabana Club,Dock on Canal,PET Friendly, Pickle ball courts

~ Ocean Isles ~ Brand New Waterfront Condo w/ Pool! #27

2.0 star property
9.2 out of 10, Wonderful, (7)
"Property is as listed, great central location in Marathon. Condo was clean, awesome laundry in unit. No issues during our stay, would visit again!"
~ Ocean Isles ~ Brand New Waterfront Condo w/ Pool! #27

Waterfront Dream Condo with Panoramic Views, Near Vaca Cut

10.0 out of 10, Exceptional, (70)
"We really enjoyed our stay. The owners are very welcoming and communicate well. The condo was well appointed and very comfortable. The views from the balcony are wonderful and it’s a quiet place to just sit and relax! Don’t hesitate to book! "
Waterfront Dream Condo with Panoramic Views, Near Vaca Cut

Salt Life: Experience Coastal Luxury, 2BR KCB Condo W/ Breathtaking Ocean Views, Shared Pool & Beach

10.0 out of 10, Exceptional, (15)
"Very pleased with every aspect."
Salt Life: Experience Coastal Luxury, 2BR KCB Condo W/ Breathtaking Ocean Views, Shared Pool & Beach

Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

2.0 star property
9.0 out of 10, Wonderful, (4)
"Unit was very clean and recently remodeled. The building was a little difficult to find in the dark at night, but I would definitely recommend staying here again."
The price is AU$598
includes taxes & fees
14 July - 15 July
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL
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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Frequently asked questions

How much do condos in Grassy Key cost?
Condos in Grassy Key range from AU$593 to AU$598 per night. This means extra room for the entire family at a price that doesn't break the bank. This price was 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.
How many condos are there in Grassy Key?
Grassy Key has 161 condos. To help you find the perfect stay, use our filter tool to search for the amenities or perks you need.
What is there to do in Grassy Key near my condo?
You'll find tons of wonderful things to sink your teeth into in Grassy Key. Head for big attractions like Curry Hammock State Park, Coco Plum Beach and Florida Keys Aquarium Encounters. Crane Point Museum and Nature Centre, Captain Hooks Marina and Dive Centre and San Pablo Catholic Church are also visitor favourites.