
Villa vacation rentals in Grassy Key
Find and book unique villas on Airbnb
Top-rated villa rentals in Grassy Key
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Grassy Key villa rentals
Private villa rentals

Isla Guava: Waterfront Htd Pool, Dock, Walkable
Amazing place, you can’t beat the location and property. The house was exceptionally clean and the host was very friendly and easy to communicate with. We will definitely return!!

Picturesque Villa Near History of Diving Museum
Beautiful accommodations and gorgeous grounds to relax by the ocean and pools. Highly recommend!

Guest Spring Break Stay: Resort Amenities & Views
Our stay at this house was absolutely perfect! The home itself was spacious, beautifully maintained, and had everything we needed for a comfortable and relaxing getaway. What made it even better was the access to the resort amenities like pools, restaurants, and activities, all just a short distance away. It truly felt like having the best of both worlds: the privacy of a home with the luxury of a resort.

Spring Break Lux: 5-Star Villa w/ Marriott Access
We had a great stay and would definitely come back! The place was very spacious and modern and clean. Rodrigo, the host, was responsive and very helpful. Highly recommend!

2BR oceanfront with amazing views, balcony & kayak
It was quiet and comfortable. Very clean throughout. Beautiful location. Loved the decks upper and lower. I would rent again.
Luxury villa rentals

Anglers Reef Islamorada
Our family of 5 loved our time in Islamorada. The community was beautiful and quiet. It was definitely mostly retired couples but everyone was friendly with our young kids. The condo was bigger than the pictures made it seem- we had more than enough space. Everything was clean and we had everything we needed.

Villa Sombrero
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.

Indigo Reef water view Villa- #1 Guest Favorite
We absolutely loved our stay and can’t wait to return! The unit was pristine and we loved watching the sunsets from the porches. The pool was pristine and never crowded. The hosts were amazingly responsive and helpful.

Lux Villa for Spring Break: Pool, Kayak & Marriott
I had an amazing time around, Josie was amazing and the overall attention was great, if you want to relax and have a great time around, this is your place!

Dolphin 1-Bedroom Villa
A beautiful quiet place to stay. Kayaking in the morning and swimming in the pool at night. We loved exploring other Florida Keys and coming back to sleep. Easy check in and out.

3 EnSuite Bedrooms! Waterfront Resort, Pool, Dock!
This house was perfect for our family of 5 for Spring Break. The canal at the back was perfect for fishing, kayaking and SUP. The pool was lovely and warm. The house and grounds were so beautiful and comfortable! We had a wonderful time and would stay here again in a heartbeat!

Oceanfront Villa overlooking the Atlantic
My family really enjoyed our stay at Vivian’s place! The photos do not do it justice! Very roomy, amazing water views, and beautiful decor/upgrades. Vivian had everything we needed for our stay - we traveled with a toddler and baby and everything we needed was there. Vivian was responsive and helpful. We would definitely stay again! Thanks Vivian!

Waterfront Villa (38) w/ sunset views & boat slip
Great location on the property. Beautiful view of the water and the pool. Nice big porch to relax on with plenty of chairs. Provided plenty of towels and the kitchen had everything you needed. Could have used more TB, PT and some dishwasher soap but all good. This place is a favorite of ours to just relax and go boating! Highly recommend!!
Villa rentals with a pool

2BR water view with private pool, balcony & kayak
very comfortable villa. Absolutely loved the little swimming pool. Clean and comfortable villa.

Isla Mamey: Waterfront Htd Pool, Dock, Walkable
Our family of 4 stayed for 11 nights to celebrate our twins 10th birthday. We live in Miami and brought most of our kitchen but totally wasn’t needed! Villa #5 has anything and everything kitchen wise! Everything was so clean and comfortable - need to upgrade our home pillows to match! Shared pool was always clean and warm, met so many nice people. Evening dock was awesome for catching small fish with the kids. Location is perfect for all the dining Islamorada has to offer. We can’t wait to go back! Thanks again!

Islamorada house with best location. Lic # 24-0055
Very clean and spacious. Great hosts. We did not need them during the stay but all requests were responded to promptly leading up to the stay.

2bd/2ba Ocean Retreat in Kawama Yacht Club
A beautiful unit, nice beds and everything as pictured! Paul was good on communication. However, the small community at Kawama is becoming over- crowded. Many times the pools are full and over capacity with screaming kids, and no chairs are available to just sit by the pool. Large parties are happening most every weekend, with a lot of drinking, smoking, and loud music. It’s not Paul’s fault, but the atmosphere here isn’t as quiet and kid friendly as it used to be!

Isla Mirabelle: Waterfront Pool, Dock, Walkable
The property was better than described. A great quiet getaway. At the same time a lot to do for all. For kids, a playground, park and library adjacent to the property. This is beyond what is available throughout the Keys. Looking forward to our next stay.
Destinations to explore
- Florida Keys Vacation rentals
- Key West Vacation rentals
- Miami Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Central Florida Vacation rentals
- Tampa Vacation rentals
- Seminole Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Long Beach
- Far Beach
- Sandspur Beach
- EAA Air Museum
- Cocoa Plum Beach
- Sea Oats Beach
- Theater of the Sea
- Windley Key Fossil Reef Geological State Park
- Sugarloaf Beach
- Long Key State Park
- Horseshoe Beach
- Keys' Meads
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes