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Featured Condo Rentals in Grassy Key and around

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 €303
includes taxes & fees
12 Aug - 13 Aug
Sombrero Beach Tropical Getaway in the Heart of Marathon

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

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, (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!

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

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

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, (7)
"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!

Waterfront Dream Condo with Panoramic Views, Near Vaca Cut

10.0 out of 10, Exceptional, (71)
"Amazing place to stay. Condo was as advertised and the views were incredible. Nice quiet community with very friendly people. Would definitely stay again. "
Waterfront Dream Condo with Panoramic Views, Near Vaca Cut

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 €346
includes taxes & fees
15 Aug - 16 Aug
Tropical Oasis on Sombrero Beach in the Heart of Marathon FL

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, (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

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

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

~ 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

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
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

Frequently asked questions

How much do condos in Grassy Key cost?
The price range for condos in Grassy Key is €303 to €346 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 traveller favourite 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 9.5.
How many condos are there in Grassy Key?
Pack your bags and pick from 173 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.