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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

Guest favorite
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 Islamorada
5 out of 5 average rating, 3 reviews

Casa del Mar Retreat- June-December availability

AmyRating, 5 stars2 months ago
It was the perfect get away for my daughter and I and a few friends. The house was gorgeous. The pool was so relaxing. The pier was a great location to spend time and watch the wildlife in the ocean below. The location was super convenient to shops and restaurants and lots of activities. Ani was super communicative - offering to help connect us with tours and answering questions. It was hard to leave and we will definitely be back. Thanks for a great week!!!
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.
Guest favorite
Home in Marathon
5 out of 5 average rating, 13 reviews

Beautiful Newer Home 4 Bedroom 4 Bathroom W/ Pool

AnnRating, 5 stars1 month ago
This home is wonderful. The pictures do a great job of showing you what you are getting. I searched several options in the Keys for our 8 adult travel group, but this home was the perfect fit. All of the rooms were well appointed, roomy, clean, and we felt right at home. The area is quiet and close to restaurants, grocery stores, beautiful hiking, and is right on a channel.
Home in Key Colony Beach
4.63 out of 5 average rating, 30 reviews

Waterfront Oasis with Boat Dock & Pool!

Mary CravenRating, 5 stars3 weeks 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 favorite
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!
Home in Marathon
5 out of 5 average rating, 3 reviews

Blue Bungalow New Listing Canal Front Dock Pool

CaitlinRating, 5 stars4 days ago
The house was beautiful, and well set up with all the listed amenities easily accessible. Not only was the pool and patio area a great time for adults and kids, there were supplies to also take to the beaches. We had a slight issue with one amenity and the host quickly responded to take care of it perfectly making our stay that much better.
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

Luxury mansion rentals

Home in Marathon
4.89 out of 5 average rating, 19 reviews

NEW LUXURY 4/3 SINGLE FAMILYw/HEATED P00L,BOATDOCK

BradleyRating, 5 stars10 months ago
It was an awesome place! Beautiful, clean, and cozy! You can pull your boat right up to the dock! easy access threw the canal to the ocean and a couple of restraunts! pools nice! plenty of room for a big family! All of your amenities are nearby! Grocery store, restraunts, bars if your into that, gift shops and more!
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
4.9 out of 5 average rating, 86 reviews

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

BethanyRating, 5 stars5 days ago
This listing was one of our top 3 places to stay for vacation. The house was even better than the photos. This house was packed full of every imaginable thing that you needed. Everything you could desire for cooking was there. Everything you would need for a day at the beach was there (umbrella, chairs, etc.) If you wanted to pop a kayak in the water and kayak around Boot Key, there were many kayaks to choose from. The location was also absolutely wonderful. Two grocery stores within walking distance. I’m a runner and enjoyed running around the neighborhood on the side road path. We rented a boat for the day from right down the street and was able to easily bring it to the dock to load it with snacks for our day out on the ocean. The host, Steve, was very responsive to any questions we had during our stay.
Home in Marathon

Lindsay Landing - Open Atlantic

LoriRating, 5 stars5 months ago
The house was spotless and very comfortable. The view is amazing. The welcome cooler was helpful. We had everything we needed for our week stay. There was some trash that had washed up and it was difficult to get into the water. Very peaceful location with views of the sunrise and sunset. Would recommend the house to friends.
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.
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 stars1 month ago
Greta host !!! Great place !! Would absolutely stay here again !!!!! The pool is awesome!!! Very clean !!!
Guest favorite
Home in Islamorada
5 out of 5 average rating, 5 reviews

Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!

AbbeyRating, 5 stars2 months ago
Our family loved staying at ReelCozy! It is a beautiful home- nicely decorated, spacious and has everything you need. Anglers’s Reef is also beautiful- the kids loved the pool and having a dock space four our rental boat was ideal. The primary suite has some ocean views. We loved watching the manatees in the dock area. A great place and we would like to come back again. I highly recommend Theater of the Sea, Robbie’s, Marker 88, Islamorada Fish Company.

Pet-friendly mansion rentals

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

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars1 week 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
Vacation home in Marathon
5 out of 5 average rating, 7 reviews

Luxury Beachside Retreat - Modern 5BR/5BA w/ Pool

RobRating, 5 stars2 months ago
having the private pool was great as it meant far less drama for my 2-yo granddaughter than heading to a beach. the "kids" (in their 30s) loved it, too. Also, having a bathroom for every 2 or 3 people is always a great ratio for an Airbnb.
Guest favorite
Home in Marathon
5 out of 5 average rating, 13 reviews

Private Pool, Spa, Game Room, Dock & Tiki Hut!

JodyRating, 5 stars1 week ago
Very nice and comfortable home. Super clean! ALL the appliances you could need in the kitchen! Many utensils which is imperative for a large group. Lots of seating inside and outside! Pool area secure and private. Very relaxing and beautiful! Plenty of towels/linens. Whatever we brought to Bert’s attention, he was very responsive with, and he very quickly remedied it! 5 star! Will definitely consider staying again!
Guest favorite
Home in Key Colony Beach
4.91 out of 5 average rating, 56 reviews

*Newly Renovated Single Family Home w/Private Pool

JadeRating, 5 stars1 month ago
Our family had a phenomenal time at this Airbnb. 10/10 recommend, host was fast at communicating and very helpful. Hoping to come back!!!
Guest favorite
Home in Marathon
5 out of 5 average rating, 33 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

B.J.Rating, 5 stars3 weeks ago
This was our first time to Marathon. First, Michel and Kim were very communicative from the start. They gave great beach and restaurant recommendations before we arrived. Check in was very easy and we had very thorough directions on the process. Home was very nice and clean. Pool was refreshing and relaxing. Lots of parking and could have brought a boat and trailer if we wanted. Michel and Kim checked in a couple of times during our stay to ensure things were good and asking if we needed anything. The stay was great and our first time to the Keys was amazing. We will definitely be back to the Keys and would stay at Michel’s place again!
Guest favorite
Home in Summerland Key
4.94 out of 5 average rating, 89 reviews

Waterfront Anchor House with Boat Basin & Ramp!

SpyRating, 5 stars1 month ago
Great house on the water. Convenient location to access other keys. Easy walking distance to a great restaurant
Guest favorite
Home in Marathon
4.97 out of 5 average rating, 59 reviews

Paradise Ocean Front 4/3Home Heated Pool

TriciaRating, 5 stars2 months 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
4.87 out of 5 average rating, 15 reviews

Key Colony Beach-POOL & DOCK

DanielleRating, 5 stars2 weeks ago
John was super easy to communicate with, very responsive and if I had any issues he responded promptly!! We will definitely be coming back to this house next summer!! Thanks for a great stay!

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