Mansion holiday rentals in Key West

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Popular amenities for Key West mansion rentals

Luxury mansion rentals

Top guest favourite
Home in Marathon
5 out of 5 average rating, 12 reviews

Luxury 5Bdrm/6bath New in 2024

CatherineRating, 5 stars2 weeks ago
Timothy’s house was spacious, comfortable, and clean. The pool was a great way to beat the Florida Keys heat and the sunset views from the 3rd floor were awesome! Boaters will love the boat ramp next door. The fish cleaning table and outdoor freezer were a huge plus.
Superhost
Townhouse in Marathon
5 out of 5 average rating, 3 reviews

Bayside Paradise

JudithRating, 5 stars4 months ago
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!
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

Sombrero Siesta Heated Pool & Stunning Canal Views

JustinRating, 5 stars1 month ago
Wonderful stay and the place was perfect!
Guest favourite
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 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!
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 stars3 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.

Pet-friendly mansion rentals

Guest favourite
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
Home in Marathon
4.92 out of 5 average rating, 26 reviews

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

AnneRating, 5 stars1 month ago
We Loved our stay so much! Matt was a wonderful host! The location is amazing. Our daily visitors of manatees and iguanas made it so special!
Guest favourite
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 favourite
Townhouse in Key Largo
4.93 out of 5 average rating, 74 reviews

Divers Delight with Golf Cart, 2 Kayaks, Pool

NicoleRating, 5 stars1 month ago
Wonderful location! Pool right out the back door. The lagoon was great for kayaking and snorkeling! The condo was clean and had plenty of beds. Diane was always quick to respond!
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 19 reviews

Paradise Found ~ Waterfront Pool Home, 50' Dock

TinaRating, 5 stars3 months ago
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!!! ♥️
Top guest favourite
Home in Marathon
5 out of 5 average rating, 16 reviews

Waterfront home w/pool, dock & close to beach

ElaineRating, 5 stars1 month 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!
Guest favourite
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.
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 24 reviews

Modern Island Luxury | 4 En-Suite Masters, 6 BA, P

BrianRating, 5 stars2 months ago
We booked the Snapper House last minute for a group of 7 and everything worked out perfectly. The house was extremely clean and perfectly set up for an Airbnb, with a great design that made our trip really comfortable. Marjorie and Sean were fantastic to work with and provided clear and proactive communication throughout the stay. We were able to rent a boat from a nearby place and take full advantage of the dock for boating and fishing. We also enjoyed the pool deck, ping pong table and outdoor grill area. We'd gladly book here again!

Mansion rentals with a pool

Home in Key West
5 out of 5 average rating, 4 reviews

Beautiful quiet neighborhood. Sunsets! Huge Pool!

DiegoRating, 5 stars9 months ago
I chose this house for our summer vacation with my family, and I have to say, it was absolutely spectacular. Upon arrival, you drive up to a stunning view of the pool and the beautiful water right in front of the house. Inside, the rooms are spacious with incredibly comfortable beds. The kitchen is a dream, and you can enjoy the sea view while cooking, relaxing in the living room, or from the balcony. The pool and yard quickly became our favorite spots, where we spent most of our time. The pool was always clean, with Samantha ensuring the maintenance team stopped by weekly. We also had access to a grill, which we used for amazing BBQs while watching the breathtaking sunsets that this home offers. The deck is another highlight, with two beautiful chairs perfect for relaxing with a book or chatting with loved ones. You can even park a jet ski or small boat right on the deck, which can be rented from local companies who will deliver it directly to the house. unforgettable vacation.
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.
Guest favourite
Villa in Key Largo
4.87 out of 5 average rating, 15 reviews

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

IsaiasRating, 5 stars3 days ago
Words can’t describe how amazing the unit was. The pictures don’t do any justice. When I arrived I reached out to Josie for further instructions and she quickly responded. Upon entering the unit we immediately felt the warmth and welcome. I would recommend to any family of 8 in Key Largo area.
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
5 out of 5 average rating, 3 reviews

Blue Bungalow New Listing Canal Front Dock Pool

CaitlinRating, 5 stars3 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
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 6 reviews

Plentiful 4 BR, Pool Club, On Canal. 3 Level Home

JpRating, 5 stars1 week ago
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.

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