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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Browse Select Grassy Key Condo Rentals

Indigo Reef Resort Villas & Marina by KeysCaribbean
Relax by the serene pool surrounded by lush palm trees and shaded lounge chairs.

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
Relax by the pool surrounded by lush greenery and a shaded lounge chair.

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 £297
includes taxes & fees
3 Aug - 4 Aug
Sombrero Beach Tropical Getaway in the Heart of Marathon
Canal-front condo with amazing views & convenient location
Relax by the pool with lounge chairs and sunbeds under shaded umbrellas and palm trees.

Canal-front condo with amazing views & convenient location

8.6 out of 10, Excellent, (42)
"The condo was located near sombrero beach, which is very nice. The pool area offered many different activities. The pool bar was always a good time."
Canal-front condo with amazing views & convenient location
The Reef at Marathon
Guests can enjoy stunning views of the marina from the comfort of their accommodations.

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!
Enjoy the tranquil ocean views from a comfortable bench near the shore, surrounded by palm trees and a stone wall.

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

10.0 out of 10, Exceptional, (201)
"Great place and location, excellent resourceful and pleasant host "
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!
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, coffee maker, and sink.

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 Tropical Beach White Sand-No Stairs-King Bed-Heated Pool- Superfast WiFi
Relax on the beach with picnic tables and benches amidst palm trees.

Private Tropical Beach White Sand-No Stairs-King Bed-Heated Pool- Superfast WiFi

10.0 out of 10, Exceptional, (79)
"Everything was great. "
Private Tropical Beach White Sand-No Stairs-King Bed-Heated Pool- Superfast WiFi
Tropical oasis near all the action with central AC & balcony
Enjoy cooking and dining in this well-equipped kitchen with a central island and dining area.

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
Relax by the serene pool surrounded by palm trees and thatched umbrellas.

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
Enjoy cooking in this well-lit kitchen with a large island, stove, and sleek backsplash.

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
Guests can enjoy stunning marina views from the hotel's waterfront location.

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!
Relax in a serene outdoor setting with a thatched-roof gazebo, lounge chairs, and a pathway to the beach.

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
Relax in a beach chair under the shade of a palm tree, overlooking the ocean.

BEACHFRONT CONDO on Coco Plum Beach with Heated Pool

9.8 out of 10, Exceptional, (57)
"We love Coco Plum! Communication with the property manager was smooth, the condo was very clean, fully stocked, comfortable, and has a great view of the pool and ocean. The screened lanai was great for evenings outside without the bugs. We hope to go back next year. "
BEACHFRONT CONDO on Coco Plum Beach with Heated Pool
Cozy condo with shared pool, tennis court, ping pong table, W/D, central AC
Enjoy the view from this balcony with a wicker chair and glass table, overlooking the surrounding area with a street and trees.

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!
Relax by the resort's central pool surrounded by palm trees and lounge chairs, with ocean views and a marina nearby.

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

10.0 out of 10, Exceptional, (155)
"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
Relax by the pool surrounded by comfortable lounge chairs and shaded by green umbrellas.

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

9.4 out of 10, Exceptional, (61)
"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
Relax under the shade of this beachside structure, surrounded by sandy shores and a serene ocean view.

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

2.0 star property
9.4 out of 10, Exceptional, (8)
"Great overall stay very secluded area with a great view"
~ Ocean Isles ~ Brand New Waterfront Condo w/ Pool! #27
Waterfront Dream Condo with Panoramic Views, Near Vaca Cut
Guests can enjoy ocean views from the resort's multi-story buildings with flat roofs and balconies.

Waterfront Dream Condo with Panoramic Views, Near Vaca Cut

10.0 out of 10, Exceptional, (71)
"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
Enjoy the ocean view from this balcony with a ceiling fan, two chairs, and a view of the sandy beach and pier.

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

10.0 out of 10, Exceptional, (14)
"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
Relax by the pool surrounded by lush greenery and a shaded lounge chair.

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 £306
includes taxes & fees
30 Aug - 31 Aug
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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Top Grassy Key Hotel Reviews

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

10/10 Excellent
"Very nice well kept property with a feel for being in nature. The grounds/plantings are well kept and tropical feeling with a butterfly garden yard games, 2 pools and more. The only downside was no beach. But, if you are patient you can spot some very cool fish from the docks"
Sharon 3-night trip
Posted 2 days ago
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is £297 to £306 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?
Select from multiple condos in Grassy Key with a total average guest review rating of 9.5. The Reef At Marathon By Capital Holidays comes highly rated if you've got the kids in tow or just want some extra space. This 3-star property also offers a marina and a nearby waterfront. Indigo Reef Resort Villas And Marina By Keyscaribbean is another popular option. It has a 3.5-star rating and amenities such as a swimming pool and a dock.
How many condos are there in Grassy Key?
Pack your bags and pick from 194 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.