
Holiday houses in Grassy Key
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Grassy Key
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Grassy Key holiday rentals
Other great holiday rentals in Grassy Key
Guest favourite

Home in Marathon
4.94 out of 5 average rating, 35 reviewsFlorida Keys Oceanside Utopia
CaroleRating, 5 stars1 month ago
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!
Superhost

Condo in Duck Key
4.85 out of 5 average rating, 94 reviewsVilla 5087 on Duck Key BOAT SLIP available
JadenRating, 5 stars3 weeks ago
Great stay, would highly recommend, home was clean and quiet. Can’t wait to come back to duck key so I can book again.
Guest favourite

Home in Key Colony Beach
4.99 out of 5 average rating, 107 reviewsABeachBungalow-60’dock w/ access to pool and beach
DesireeRating, 5 stars1 month ago
We enjoyed our stay and felt very at home. I had a few questions when settling in and I got responses very quickly. The house was tidy, the location was perfect and the kayaks were fun (be careful getting in the water as the rocks are very slippery). The owners recommended babyquip which was very helpful in providing toys, a crib and a high chair for my little ones.

Villa in Marathon
4.76 out of 5 average rating, 152 reviewsSunset Villa in Duck Key
HeatherRating, 5 stars3 days ago
It was one of cleanliness Villas I have stayed in . We have been vacationing on Duck Key for 20 plus years and would definitely recommend 5085 - great location , very reasonable price and very simple easy check in and check out instructions. Thank you .
Top Guest favourite

Home in Marathon
5 out of 5 average rating, 51 reviewsLuxury Boating Paradise+Pool+Sailing Kayaks
RickRating, 5 stars2 weeks ago
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!
Superhost

Home in Marathon
4.93 out of 5 average rating, 29 reviewsSerenity Bay Estate-FL Keys Best Kept Secret! Beau
JerrieRating, 5 stars6 months ago
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!

Townhouse in Duck Key
4.72 out of 5 average rating, 280 reviewsSunset Views!
MichaelRating, 5 stars4 weeks ago
So great look forward to the next time I'm down in the keys here beautiful
Superhost

Apartment in Marathon
4.86 out of 5 average rating, 50 reviewsLittle Venice in Marathon (in the Beautiful Keys)
AlisonRating, 5 stars3 weeks ago
We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!
Destinations to explore
- Florida Keys Holiday rentals
- Key West Holiday rentals
- Miami Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Central Florida Holiday rentals
- Tampa Holiday rentals
- Seminole Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Cannon Beach
- Conch Key
- Calusa Beach & Loggerhead Beach
- Cocoa Plum Beach
- Theater of the Sea
- EAA Air Museum
- Long Beach
- Horseshoe Beach
- Far Beach
- Sea Oats Beach
- Sugarloaf Beach
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads