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Mansion vacation rentals in Key West

Find and book unique mansions on Airbnb

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Popular amenities for Key West mansion rentals

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 favorite
Home in Summerland Key
4.87 out of 5 average rating, 39 reviews

Powell Family Resort

JohnRating, 5 stars4 weeks 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 favorite
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 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
Guest favorite
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.
Top guest favorite
Home in Big Pine Key
5 out of 5 average rating, 10 reviews

Hibiscus House

ReginaRating, 5 stars1 week ago
We love to travel and have stayed in quite a few airbnbs now but this one has gotten 5 stars from all the adults and the kids! This spot is so unique we all loved it! It’s beautiful inside and out. The wildlife comes right up into the yard. Every evening we have a family of deer show up. I think this was everyone’s favorite part but the loved the pool and the deck and the space the home has. Plenty of seating to separate or spend some time as a family. We are definitely coming back to this unit when we come back to the keys and we’ve been telling all our friends and family about it for their next trip! The host was great and very responsive!

Luxury mansion rentals

Top guest favorite
Vacation 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!
Home in Marathon
4.89 out of 5 average rating, 85 reviews

4 Bed/3.5 bath with private pool, tiki hut & dock!

H.E.Rating, 5 stars3 weeks ago
Excellent location Nice open layout Had lots of water toys.
Home in Duck Key
4.67 out of 5 average rating, 157 reviews

4/2.5 - Pool Home and Village and Hawks Cay 7222

RyanRating, 5 stars1 month ago
Our family had a great time in Duck Key. The pool area was relaxing and our family spent most of our time here. We had an amazing five days in the keys and would definitely rent here again. We cannot wait to come back.
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).
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 favorite
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
Guest favorite
Villa in Islamorada
4.98 out of 5 average rating, 47 reviews

luxury & fishing bigdavechartersandtours.comm -1m

ToddRating, 5 stars3 weeks ago
Greta host !!! Great place !! Would absolutely stay here again !!!!! The pool is awesome!!! Very clean !!!
Home in Marathon
5 out of 5 average rating, 5 reviews

The Happy Place

ErikaRating, 5 stars3 months ago
The house is definitely dated and had a bit of a musty smell when we walked in. However, you cannot beat the view. The pool area was beautiful and the water all around it just made it perfect. There were a few things that didn't work and the internet was spotty, but that only really matter at night when we wanted to relax. It is a top contender (once we know how many bedrooms we need) for our trip next year!

Pet-friendly mansion rentals

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

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars2 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.
Superhost
Home in Marathon
4.92 out of 5 average rating, 25 reviews

Steps to Sombrero Beach | 4BR w/ Dock, Pool + Dogs

DianeRating, 5 stars1 month ago
We thoroughly enjoyed our week at Matt’s place! As a host, Matt was quick to answer our questions and provide what we needed. The location is excellent, with the canal views from the back yard and a few minutes walk to the beach.
Guest favorite
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.
Top guest favorite
Home in Marathon
5 out of 5 average rating, 16 reviews

Waterfront home w/pool, dock & close to beach

ElaineRating, 5 stars4 weeks ago
Our family (of six adults) had the most wonderful two weeks in Ruth’s beautiful home, and we loved every single minute of it, apart from our departure as we all wanted to stay! The house is absolutely beautiful, spotlessly clean and very well equipped. The refrigerator/kitchen was thoughtfully stocked with a very generous supply of breakfast items and other snacks, and there were fresh flowers in place. We were lucky enough to have manatees visiting us a few times, which was an incredible experience. The location is amazing, and after travelling the length and breadth of the Keys, it is definitely the best place to be. Ruth was the best ever host - very hospitable & responsive, and we cannot thank you enough! We really can’t wait to come back! Thank you so much!
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 favorite
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 Key Colony Beach
4.86 out of 5 average rating, 14 reviews

Key Colony Beach-POOL & DOCK

BillRating, 5 stars3 weeks ago
John is a Super Host to us. He was very easy to communicate with. We had an issue at the house and he had it dealt with before lunch the next day. Unexplainably, we ended up leaving our fish rods in the back porch area (out of site out of mind?). John gathered them up and his wife took them to UPS to get them packed and sent back to us. Well above and beyond anything we could have expected. Our thanks to both of them.
Superhost
Home in Summerland Key
5 out of 5 average rating, 3 reviews

Waterfront Beach House with Dock & Heated Pool!

HeatherRating, 5 stars3 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.

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