
Mansion holiday rentals in Key West
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Top-rated mansion rentals in Key West
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Luxury mansion rentals

Powell Family Resort
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.

Casa del Mar Retreat- June-December availability
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!!!

Oceanfront Pool Home - 130ft Dock & Canal Garden
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.

Gorgeous 4-bedroom home with 8-person hot tub
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!

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

Waterfront Oasis with Boat Dock & Pool!
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).

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

Airbnb Exclusive Offer! 51' Catamaran Yacht
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

Waterfront Escape -VACA-23-408
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.

Bayside Paradise
Jose’s place was the perfect getaway for our high school baseball team’s preseason opening game weekend! The boys had a great time swimming, kayaking, fishing, grilling, and enjoying a little slice of heaven in the Keys! Jose was an excellent host and facilitated all of our specifics wants and needs for our trip. We were extremely blessed by the refreshing hospitality and attention to detail. Our team made many wonderful memories here! We would love to return next season for another great stay! Thank you, Jose, for making us feel like royalty!

*Newly Renovated Single Family Home w/Private Pool
Our family had a phenomenal time at this Airbnb. 10/10 recommend, host was fast at communicating and very helpful. Hoping to come back!!!

Paradise Found ~ Waterfront Pool Home, 50' Dock
Highly recommend Coco Plum!! Top notch!! Their attention to us was amazing! Everyday asking how things were going? Making sure we were comfortable and if we needed everything. Having texting conversations with quick responses was like talking to your best friend! The property had everything and I mean everything we ever needed!! So beautiful, so clean so amazing! Our family was so comfortable and raved over it constantly! We will only rent from Coco Plum for all our future vacations!!! Five stars is not enough!!! Thank you so much!!! ♥️

Waterfront home w/pool, dock & close to beach
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!

New Paradise On Sombrero Beach
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!

Paradise Ocean Front 4/3Home Heated Pool
Our stay was fantastic, great location and view. The house is set up perfectly if you have several people staying.

Extra Lux Grouper House w/4 Master Suites, 6 BA,
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.
Mansion rentals with a pool

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

Lindsay Landing - Open Atlantic
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.

4/2.5 - Pool Home at Village at Hawks Cay 7222
This was a beautiful house in a very nice community. The host was friendly and described everything perfectly. Beds were comfortable and clean.

Blue Bungalow New Listing Canal Front Dock Pool
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.

Marathon Peach Pit
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

Plentiful 4 BR, Pool Club, On Canal. 3 Level Home
We've been vacationing in Key Colony for years, and this place has a lot going for it. Having the canal and dock was a huge plus—we made good use of it. The Cabana Club access is always a win, and everything was super clean, easy, and very comfortable. Great spot, great stay. We’ll definitely be back.

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

luxury & fishing bigdavechartersandtours.comm -1m
Greta host !!! Great place !! Would absolutely stay here again !!!!! The pool is awesome!!! Very clean !!!
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