Villa vacation rentals in Key West

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

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Key West villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Beachfront villa rentals

A serene outdoor pool area is surrounded by palm trees, with covered cabanas offering relaxation spots. Soft lounge chairs are positioned nearby, and the tranquil water reflects the colors of the sunset sky, enhancing the peaceful atmosphere.

5 out of 5 average rating, 4 reviews

Florida Keys | Exclusive Resort Amenities | 2BR

RobertRating, 5 stars4 days ago

Seamless transactions, very communicative. Everything went according to plan.

The view from the patio showcases a vibrant sunset reflecting on the tranquil water. Lush palm trees frame the scene, with the illuminated pool area visible below. A distant pier extends into the water, enhancing the serene ambiance of the location.

4.76 out of 5 average rating, 143 reviews

Sunset Villa in Duck Key

SaritRating, 5 stars1 week ago

I had a wonderful stay at Gabriel’s house! The home was very welcoming and spotlessly clean, with an absolutely amazing view. Gabriel was a fantastic host—super friendly and always quick to respond to any questions. I would definitely recommend this place to my friends and would love to stay here again!

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!

Top guest favorite

A charming two-story villa is framed by swaying palm trees against a bright blue sky. Lush greenery borders the pathway leading to the entrance, which features a porch with round windows and white railings, emphasizing the inviting exterior of the residence.

5 out of 5 average rating, 13 reviews

Seas the Keys Getaway

BonneRating, 5 stars5 days ago

I had a wonderful day for a very relaxing vacation. I know the property Hawks Kay and I am delighted in it. Carmen and Scott are very gracious house and everything was just wonderful

A two-story house with a light-colored exterior overlooks a serene canal. A spacious deck with turquoise lounge chairs surrounds a clear pool. Tiki huts provide shaded seating, while palm trees add to the tropical ambiance. Large glass doors open to the indoor living area.

4.98 out of 5 average rating, 42 reviews

luxury & fishing bigdavechartersandtours.comm -1m

SarahRating, 5 stars3 weeks ago

Great house, loved the pool. Would definitely stay here again!

An outdoor lounge area features a private spa pool surrounded by tropical plants and seating. Soft lighting creates a welcoming atmosphere, while the vibrant sunset sky adds a colorful backdrop. Sliding doors connect the space to the interior of the villa.

4.89 out of 5 average rating, 90 reviews

Villa in Paradise. Plunge pool. Middle of the Keys

KaceyRating, 5 stars2 weeks ago

We had an amazing Keys vaca with the family and it centered around this home. The house itself was exactly as described, and perfectly clean. The location is in the middle of everything but still tucked away. Alex’s instructions and responsiveness gave a personal touch that other accommodations lack. We would definitely stay again. Thank you for sharing your home with us!

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Villa rentals with a pool

Top guest favorite

5 out of 5 average rating, 6 reviews

Isla Key Lime: Waterfront Htd Pool, Dock, Walkable

LeighAnnaRating, 5 stars2 weeks ago

we have been to islamorada several times and this is my favorite place we have stayed! it was clean, beautiful, and in the perfect location! right in the middle everything! we enjoyed it and will definitely be back!

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.

4.77 out of 5 average rating, 13 reviews

Oceanfront Spring Break Villa: Resort Perks

AmandaRating, 5 stars3 weeks ago

What a beautiful place! We still can't get over it. It must be brand new and so well kept. The furniture was so nice and high end, I hope other guests treat it like the gem that it is! More room than needed for two adult couples. Easy walk to neighborhood pool with ocean views. The access to the resort is about an 11 minute walk cutting through a busy street. But was easy to drive over and park at the resort, so not too bad. Can't wait to stay again- it really is a bang for the buck if you compare a hotel ROOM per night VS the 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!

5 out of 5 average rating, 3 reviews

Isla Lychee: Little Basin Villas, Waterfront

NathanielRating, 5 stars3 weeks ago

The villa was squeaky clean when we arrived, our family really loved the pool, grill and docks for fishing and paddle boarding. Thank you for having us.

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!