Mansion holiday rentals in Key West

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Popular amenities for Key West mansion rentals

Luxury mansion rentals

Top guest favourite
Holiday home in Key Colony Beach
5 out of 5 average rating, 16 reviews

Gorgeous 4-bedroom home with 8-person hot tub

AngieRating, 5 stars5 months ago
This house was awesome!!!!!!! So clean and organized and it had everything you could possibly need!!! We took our boat and it was wonderful having it right at the dock! Hot tub, fish cleaning station, outdoor dining table! David was super responsive and we will definitely go back! We enjoyed the grill and the outdoor bikes and it was wonderful having an ice machine! Bedrooms large with soooo much storage! Bathrooms awesome too! Just can’t say enough good things about this air b and b and the host David! Great restaurants around by car and by boat. The dock was perfect place to sit and have coffee in the Adirondack chairs on the canal! Lots of friendly neighbors! Very quaint and quiet neighborhood and felt safe on my morning runs! Sunset park half mile away! Loved it!
Guest favourite
Home in Key West
4.96 out of 5 average rating, 25 reviews

Private Parking & Pool - The Delaney House

Louis AmbroseRating, 5 stars1 month ago
Our stay was perfect! Location could not be beat!
Home in Key Colony Beach
4.63 out of 5 average rating, 30 reviews

Waterfront Oasis with Boat Dock & Pool!

Mary CravenRating, 5 stars1 week ago
We had a really great stay here - 2 families of 5 and there was room for everyone to sleep. There’s a pullout sofa in a smaller office room that one 14 year old slept on. There’s house is super clean and the hosts were very helpful even after hours when we asked them to help put cold groceries away at 10 pm due to our flight be delayed!! It was so appreciated to salvage all the money we spent on them. Thank you!! The backyard is very private and has tons of beautiful trees and plants and our 6 kids loved the pool after our days on the boat. We had a boat and it was a little tricky to park at the dock bc a little tight at the end of the canal but it was fine even at low tide. We’d stay here again for sure especially based on the great customer service by the management company (although house is listed for sale so might not be available).
Guest favourite
Villa in Marathon
4.88 out of 5 average rating, 58 reviews

New Paradise On Sombrero Beach

JenniRating, 5 stars1 month ago
The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!
Superhost
Townhouse in Key Colony Beach
4.71 out of 5 average rating, 7 reviews

Both Units of Duplex w/ Cabana Club's Pool & Beach

SusanRating, 5 stars5 months ago
This was a great option for our group of 2 couples and 2 singles. Very comfortable, with good areas for socializing, nice beds, excellent kitchens and brand new grills for preparing meals at home, short walk to beach club with beautiful pool, hot tub, bar & food, and small but lovely sandy beach. And though we are not golfers, we had fun at the nearby par-3 golf course. The host was extremely responsive and friendly, and exceptionally accommodating to our needs. We hope to return next year!
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 62 reviews

Luxury 4/3 Waterfront/Private Heated Pool/Dock/Ice

KimberlyRating, 5 stars2 weeks ago
We enjoyed our stay and had a very relaxing and worry free vacation. The house had everything we needed and more. Jorge was very attentive! The beds were very comfortable. The pool and ice machine were added bonuses!! The location was very convenient and close to all the places we enjoy visiting while in the Keys.
Home in Marathon
4.95 out of 5 average rating, 22 reviews

Mar Azul Luxury Open Water 4 Bed/4.5 Bath Paradise

TravisRating, 5 stars12 months ago
This house was absolutely awesome. There was lots to do in the local area. we fished from the dock, bbq'd, swam...too much to say. Katie was responsive and quickly handled any issue we had. the kitchen was beautiful. However not many of the pots and pans work on the stove.
Boat in Key West
4.81 out of 5 average rating, 26 reviews

Airbnb Exclusive Offer! 51' Catamaran Yacht

StevenRating, 5 stars3 weeks ago
The location is great, the quality of the boat and everything was also great. The charter experience was very cool as well. Just ensure you are able to check in before 5pm as it can cause issues.

Pet-friendly mansion rentals

Guest favourite
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars3 days ago
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.
Guest favourite
Home in Marathon
4.94 out of 5 average rating, 18 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

JosephRating, 5 stars1 month ago
Great property, location and responsive, helpful hosts. I stayed with my kids and in-laws and had a great time. The beach is an easy 10-15 minute walk and the pool/backyard was a very nice place to hang out. Relatively easy access to the Atlantic side via boat if you’re planning to bring or rent a boat. The house was very clean as well. I would definitely stay here again.
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Lower Latitudes | 5/3 w pool, dock, close to beach

SkilarRating, 5 stars2 months ago
the house was beautiful & the host had very clear instructions and answered any questions we had. perfect location. manatees came right up to our dock of the house! don’t provide a ton of amenities for the price of the house but everything else made it worth it. we had the best vacation!
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 59 reviews

Paradise Ocean Front 4/3Home Heated Pool

TriciaRating, 5 stars1 month ago
Our stay was fantastic, great location and view. The house is set up perfectly if you have several people staying.
Superhost
Home in Summerland Key
5 out of 5 average rating, 3 reviews

Waterfront Beach House with Dock & Heated Pool!

HeatherRating, 5 stars4 weeks ago
House was very clean, host very responsive, beautiful location, pool was perfect and the view was amazing. Definitely recommend and will be staying there again.
Superhost
Home in Marathon
5 out of 5 average rating, 17 reviews

Grouper House, Lux 4BR, 6BA home w/ pool, dock and

MartinRating, 5 stars2 months ago
The Grouper house was fabulous. I stayed there with my wife and kids for a week. Everything about this place was top notch. From booking to check in and check out. Her staff is nothing short of superb. Sean makes sure every need or question is answered promptly. The best place I have ever stayed. Highly recommend.
Guest favourite
Home in Islamorada
4.91 out of 5 average rating, 55 reviews

Beach Cottage with pool, Dock and beach access

BethRating, 5 stars3 weeks ago
This house is in a good location and the pool is a definite plus. It was fun watching the neighborhood fishermen bringing in their catches. Being from the west we enjoyed the resident iguanas and the manatee in the channel.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 40 reviews

Dock Pool Home by Sombrero Beach

MatthewRating, 5 stars1 month ago
My family and I had a great stay at Franks place. Had a few minor things happen but Frank was able to accommodate us in a timely manner and took care of everything. The communication was great. Great location, good dock space, and a nice pool. Overall we had a great stay.

Mansion rentals with a pool

Home in Marathon
4.87 out of 5 average rating, 77 reviews

Summer Sale~New 4/3/pool/40f dock

AliaRating, 5 stars3 months ago
We loved our stay in Marathon with my two small children. Jacqueline’s place was clean and in such a great location. We spent hours enjoying the heated pool and sitting on the deck enjoying our coffee. The location is very quiet and peaceful. I’d highly recommend staying here!
Guest favourite
Home in Summerland Key
4.87 out of 5 average rating, 39 reviews

Powell Family Resort

JohnRating, 5 stars1 month ago
Great host and great location. Can’t say enough how relaxing and enjoyable the location is. Everything you need with great privacy. A wonderful time had by all.
Home in Marathon
5 out of 5 average rating, 4 reviews

Oceanfront Pool Home - 130ft Dock & Canal Garden

CourtneyRating, 5 stars7 months ago
Beauty abound! Perfect place to fish, enjoy the breeze and salt air. The quaint pool was perfect for my children to swim in while the adults relaxed in multiple different comfy furniture locations. The big windows gave way to the scenery everywhere, and the kitchen was stocked full of all kinds of cooking tools needed to host a large family vacation. Very spacious house for 10 people, as well as tons of room to explore outside. The outdoor couches under the palm trees were one of our favorite spots, and the canal provided plenty of fish for us to catch each day.
Home in Marathon
4.89 out of 5 average rating, 64 reviews

Island Dreamz Bay House -Modern 5 Star, Pool/Dock

JessicaRating, 5 stars2 months ago
We had a great stay at this airbnb in marathon! The house is stunning, and it was perfect for our family of 8. Everyone from my grandparents to my kids were super happy. The open concept kitchen was perfect for preparing meals together, and we ate most of them on the beautiful balcony. The pool was awesome, everything was clean, and location was great. We visited both the northern and southern ends of the keys during our stay and we loved our central location to everything. I would absolutely stay here again, and recommend this property to anyone with a similar size group. Everyone had their own bathrooms, the beds were comfortable, there were 2 sets of washers/dryers (which was amazing) and the master bedroom was incredible. Great views all around, and we even saw a manatee family from the dock!
Guest favourite
Villa in Key Largo
4.86 out of 5 average rating, 14 reviews

4-Bed Spring Break Villa: Clubhouse, Pool&Marriott

JoanneRating, 5 stars3 weeks ago
We had a wonderful stay at Playa Largo Ocean Residences. I came with my family to celebrate a milestone birthday and we all had a wonderful time! The house was even nicer than I had anticipated! It was modern, nicely furnished and very clean. We all had plenty of space as each bedroom has its own private bathroom. There was ample space in the common areas and we all really enjoyed hanging out on the third floor balcony. The hosts were quick to answer any questions via the Airbnb app. Having access to the Playa Largo Ocean Marriott was a huge plus as well. We spent an entire day there and rented a cabana by the pool (which I highly recommend). The pool and beach at the hotel were perfect and we stayed to eat dinner at the poolside restaurant which had excellent food. Afterward, they have free S’mores poolside which was a fun way to end the day. Would highly recommend this location and hope to stay again soon!
Home in Marathon
5 out of 5 average rating, 4 reviews

Marathon Peach Pit

EdwardRating, 5 stars9 months ago
Andrew was a fantastic host. He provided multiple ways to communicate with him, and was always responsive to any questions. The house was just as described, and provided more than enough accommodation for our group. We would definitely rent from Andrew again, it was a pleasure. The property is plenty large enough for the boat, trailer, and several cars if needed. thanks, Eddie
Superhost
Home in Key Largo
4.92 out of 5 average rating, 132 reviews

Mariners Club Resort, Best in the Upper Keys

AaronRating, 5 stars1 month ago
7 of us got together to celebrate our brother getting married, and it was super relaxing and chill. A lot of oceanic adventures and things to do in the area, plus the resort amenities was nice bonuses to enjoy, which is all exactly what he wanted. We had a swell time, and everyone was friendly in the area too. Host was communicative and everything went smoothly for us. Thank you!
Guest favourite
Home in Marathon
4.83 out of 5 average rating, 6 reviews

Sombrero Island Breeze 4BD Pool Paradise (M#9)

EricRating, 5 stars5 months ago
John is a great host, and Steve is incredible. There were a couple unforseen maintenance items that happened during our stay and response to fix items was immediately taken care of. Lots of space in the unit for our family of eight. Grandkids loved fishing off the pier and the heated pool. Definitely a vacation our family will treasure

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