Villa vacation rentals in Grassy Key

A spacious dining area features a long wooden table paired with matching benches. Bright artwork adorns the white walls, while a chandelier hangs above. Large glass doors open to a view of the outdoor space, allowing natural light to fill the room.

5 out of 5 average rating, 10 reviews

Harbor hideaway 50’dock 3Br/2Ba All amenities

TimRating, 5 stars1 month ago

Loved our stay here! Very private pool and the tiki bar/outside ice maker, was amazing. The house was clean and comfortable with the most comfortable beds ever! The only down side was the location for boating. The dock was excellent and the trip to the 7 mile bridge to fish was conveniently close, however, to do any ocean boating or fishing, the distance thru the sailboat/houseboat harbor was long and we encountered some not so friendly types through there. Over all, to stay and enjoy the privacy of the canal and pool, this was top notch!!!

A bright and spacious living area features a large dining table with wooden chairs and a central coffee table. Soft seating is arranged around a sliding glass door that opens to the outdoor patio. Decorative curtains frame the windows, enhancing natural light.

4.95 out of 5 average rating, 86 reviews

Waterfront Island Escape with Private Plunge Pool

ChristineRating, 5 stars3 weeks ago

Very well decorated, super cute, plenty of towels and extras, the outdoor porch was an amazing place to hang out. There was plenty of seating, right on the water, a fun little pool to relax in, and just the right amount of space. The beds are comfortable and the kitchen was well stocked. Everything was clean. Perfect location to visit Key West and Key Largo. We very much enjoyed our stay! Thank you

A private heated pool is surrounded by a spacious patio with laid brick flooring. Palm trees frame the scene, while a vibrant sunset casts warm colors across the sky. Lounge chairs are positioned by the pool, inviting relaxation by the serene water view.

4.95 out of 5 average rating, 136 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

StefanieRating, 5 stars2 weeks ago

My family and I stayed for a week and the house had everything we needed and more! The space was clean, comfortable and had lots of extras for the outside like pool floats, bikes, paddle boards, kayaks and more. The added touches inside like dish soap, hand soap, cleaning supplies, shampoo and conditioner was unexpected and a huge help. I was slightly surprised that this was an attached home, but there was still plenty of privacy and the location was extremely convenient. The hosts were very friendly and responsive and we would definitely recommend to others.

Top guest favorite

A scenic view of a canal is presented, featuring a circular table surrounded by several chairs on a stone patio. Lush palm trees frame the area, and a charcoal grill is positioned nearby. A dock extends into the water, offering boat access.

Villa in Key Colony Beach

5 out of 5 average rating, 27 reviews

Canal/Dock - Cabana Club - Pickleball - Remodeled

KathleenRating, 5 stars1 month ago

Very pleased with Brian 's rental, wonderful host. Unfortunately, we tried to rent for March 2026 after our first two weeks but, airbnb had already booked it to someone who wanted two months. This was our third year, i had no problem the other two years with rebooking , i was not aware of the rental practices of airbnb.

A balcony view reveals a marina filled with boats, set against a backdrop of the Atlantic Ocean. Lush green foliage lines the waterfront, while a clear blue sky enhances the scene. A couple of lounge chairs are arranged on the balcony for relaxation.

4.96 out of 5 average rating, 67 reviews

Oceanfront/2 Pools/Lagoon/Tennis/Picketball/Marina

EranRating, 5 stars2 weeks ago

We were looking for a larger stay in the keys, and Jose’s home fit the bill perfectly. It was spacious, spread over only 2 floors (vs 3 floors for most properties in Kawama). The top floor has 2 bedrooms and 2 bathrooms and is recently remodeled (incl. the kitchen and the bathrooms). The lower floor is slightly less new but still in good shape. It has the 3rd bedroom and bathroom. Provided were a club car for our use, 2 kayaks, bikes, towels, snorkeling gear… great for spending time in the lagoon (which is essentially an enclosed salt water pool). Overall great stay in Key Largo. Thank you Jose!

A serene beachfront area is presented with several white lounge chairs facing the tranquil blue waters. Rocky shoreline and greenery outline the space, creating a peaceful environment for relaxation.

4.92 out of 5 average rating, 113 reviews

Kawama Yacht Club and Molasses Reef Marine

AnnaRating, 5 stars1 month ago

Carmen's place is better than the pictures! The location couldn't be better, with many things to do & restaurants close by. Carmen communicated often and gave many details & tips that were helpful. We brought my older parents (70+) and my children (6 & 9) and all had an excellent experience. I would absolutely recommend her place.

A charming two-story villa is surrounded by lush greenery and vibrant plants, with a wraparound porch extending to the walkway. White wooden fencing offers a welcoming touch, while palm trees provide shade and enhance the tropical atmosphere.

4.95 out of 5 average rating, 135 reviews

Beach House - Kayaks & 2/2.5 Villa

SamanthaRating, 5 stars2 weeks ago

Ana was absolutely amazing and our stay was great. Her welcome book was full of awesome local recommendations for food and activities. The home was clean, the bed was comfy, and Ana was super flexible. This is probably the best stay we have had at an airbnb before.

5 out of 5 average rating, 7 reviews

Villa Marlin - Perfect Vacation in Florida Keys

ShawneeRating, 5 stars4 months ago

The home was a slice of paradise! Perfect for families to enjoy the home for the day or in the evenings after exploring the Keys. Central location to everything. The peaceful and private backyard was everything you could hope for. House is well equipped for cooking inside or outside. Jonathan was a fantastic host and responded within minutes to our questions. We will hold fond memories of this house and Christmas spent here. Thank you, The Grangers

Superhost

A private hot tub sits on the rooftop terrace, surrounded by a white railing. Lush greenery fills the foreground, while a view of the Gulf coast extends towards the horizon under a clear blue sky.

4.92 out of 5 average rating, 12 reviews

Florida Keys Wellness Gem Tranquility & Activity

EuniceRating, 5 stars6 months ago

Our stay was thoroughly enjoyed. The condo was exactly as described. Our host even provided starter sets to get us three a few days. The location was easily accessible and in walking distance to a few restaurants and the best ice cream we had ever had. Kirsten and Danielle were quite helpful and responsive when we had questions. Thank you, for the most enjoyable stay.

A serene scene features palm trees silhouetted against a vibrant sunset sky. Warm hues reflect on the water's surface, while string lights hang delicately, adding a soft glow to the beachfront area. A sandy space below invites relaxation and enjoyment of the coastal view.

4.85 out of 5 average rating, 41 reviews

(#4)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

CherylRating, 5 stars2 months ago

Susan and Dale were on-site, extremely responsive and helpful. We had a great sunset boat ride, great conversation, the pool was clean and warm and lots of sand toys everything we needed and more. We would absolutely stay again.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Grassy Key villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

5 out of 5 average rating, 6 reviews

Isla Guava: Waterfront Htd Pool, Dock, Walkable

JenRating, 5 stars3 months ago

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!!

A spacious bedroom features a wooden bed frame with a plush white comforter. Decorative pillows add a touch of color against a soft green accent wall. A bedside lamp and a wooden side table complement the cozy atmosphere.

4.67 out of 5 average rating, 49 reviews

Picturesque Villa Near History of Diving Museum

BethRating, 5 stars3 weeks ago

Beautiful accommodations and gorgeous grounds to relax by the ocean and pools. Highly recommend!

A modern clubhouse is framed by palm trees, featuring a spacious porch with white railings and several seating areas. A crystal-clear pool reflects the building, inviting relaxation. The setting is accented by lush greenery under a backdrop of soft clouds.

4.46 out of 5 average rating, 13 reviews

Guest Spring Break Stay: Resort Amenities & Views

LestrydRating, 5 stars1 month ago

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.

A modern clubhouse is depicted with a spacious balcony and large windows, surrounded by palm trees. A refreshing pool sits in the foreground, while comfortable seating areas are visible on the deck, inviting relaxation in a serene atmosphere.

4.4 out of 5 average rating, 5 reviews

Spring Break Lux: 5-Star Villa w/ Marriott Access

MelissaRating, 5 stars1 month ago

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!

A bright living room features a comfortable sofa and an armchair with decorative patterns. Light-colored walls are complemented by wood flooring. A coffee table sits in front of the sofa, and large sliding glass doors offer a view of the waterfront and patio area.

4.23 out of 5 average rating, 22 reviews

2BR oceanfront with amazing views, balcony & kayak

JanetRating, 5 stars2 months ago

It was quiet and comfortable. Very clean throughout. Beautiful location. Loved the decks upper and lower. I would rent again.

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Luxury villa rentals

A two-story villa features a cheerful yellow exterior, showcasing a spacious front porch with white railings. Lush green landscaping surrounds the entrance, with vibrant plants adding color. The well-maintained structure stands alongside other similarly styled homes in a serene and inviting neighborhood.

5 out of 5 average rating, 32 reviews

Anglers Reef Islamorada

NicoleRating, 5 stars1 month ago

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.

A sparkling pool is set against a backdrop of lush greenery and calm water. A hammock is suspended between palm trees, inviting relaxation. Surrounding the pool, well-maintained landscaping features vibrant plants and manicured grass, enhancing the serene outdoor space.

4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars28 months ago

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.

Top guest favorite

5 out of 5 average rating, 21 reviews

Indigo Reef water view Villa- #1 Guest Favorite

CaitlinRating, 5 stars2 weeks ago

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.

A modern clubhouse features a broad porch with multiple seating areas surrounded by lush greenery. A sparkling pool reflects the sky, enhancing the serene atmosphere. Palm trees frame the structure, creating a tropical vibe with clear views of the architectural details.

4.89 out of 5 average rating, 19 reviews

Lux Villa for Spring Break: Pool, Kayak & Marriott

KarenRating, 5 stars1 month ago

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!

A bright bedroom features a spacious bed with a floral throw across the bottom. Light-colored walls complement the wooden ceiling. A small armchair sits in the corner, and large glass doors lead to a balcony, allowing natural light to fill the room.

5 out of 5 average rating, 3 reviews

Dolphin 1-Bedroom Villa

KellyRating, 5 stars37 months ago

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.

An aerial view of a beautiful villa surrounded by lush greenery and palm trees. The property includes a private heated pool, lounge chairs, and a tiki hut, all set against the tranquil waterfront, with a boat dock visible along the edge of the water.

4.86 out of 5 average rating, 7 reviews

3 EnSuite Bedrooms! Waterfront Resort, Pool, Dock!

MeghanRating, 5 stars4 weeks ago

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!

A serene marina scene is captured with boats moored on calm waters surrounded by lush palm trees. The sky displays dramatic clouds illuminated by the golden hues of sunrise, creating a peaceful coastal atmosphere.

4.79 out of 5 average rating, 68 reviews

Oceanfront Villa overlooking the Atlantic

ShannonRating, 5 stars25 months ago

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!

A covered porch features four white Adirondack chairs positioned on a wooden deck. Lush green palm trees and landscaping provide a tropical backdrop, while a sparkling pool is visible in the distance, completing the serene outdoor setting.

5 out of 5 average rating, 10 reviews

Waterfront Villa (38) w/ sunset views & boat slip

KatrinRating, 5 stars1 month ago

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!!

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Villa rentals with a pool

The living area features a comfortable gray sofa and a patterned armchair surrounding a wooden coffee table. Sliding glass doors provide access to the pool area, allowing natural light to fill the room and offering views of the lush greenery outside.

4.35 out of 5 average rating, 20 reviews

2BR water view with private pool, balcony & kayak

JennaRating, 5 stars2 months ago

very comfortable villa. Absolutely loved the little swimming pool. Clean and comfortable villa.

5 out of 5 average rating, 3 reviews

Isla Mamey: Waterfront Htd Pool, Dock, Walkable

TanyaRating, 5 stars8 months ago

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!

4.88 out of 5 average rating, 17 reviews

Islamorada house with best location. Lic # 24-0055

LucaRating, 5 stars3 weeks ago

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.

4.85 out of 5 average rating, 46 reviews

2bd/2ba Ocean Retreat in Kawama Yacht Club

JanetRating, 5 stars1 month ago

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!