Some info has been automatically translated. Show original language

Mansion holiday rentals in Key West

Find and book unique mansions on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Key West mansion rentals

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 stars8 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!
Superhost
Home in Marathon
4.91 out of 5 average rating, 22 reviews

4BR Sombrero Beach House on Canal with Dock & Pool

StevenRating, 5 stars3 weeks ago
Great house, lots of room and good set-up. Beautiful backyard vista of lagoon/canal and mangrove trees, with flying fish and lots of birds. 5 minute walk to a very pretty beach. Easy access to restaurants, grocery stores and other. Peaceful.
Guest favourite
Villa in Key Largo
5 out of 5 average rating, 7 reviews

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

SpencerRating, 5 stars1 week ago
Stunning house, good size rooms, big enough for our family of 5, if you want a quiet peaceful day you can use the private pool onsite or for a bit of atmosphere the community pool over the road with lovely beach , clear water , food and drinks bar with beautiful sunsets, perfect for an evening drink, was a slight hold up with checking in but once prompted for gate and door codes everything was perfect 👌
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 stars3 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
4.58 out of 5 average rating, 12 reviews

Walk to Beach 4BR | Dock | Dog Friendly | Pools

HayleyRating, 5 stars10 months ago
Just want to write an updated review since most of these are older. The previous reviews about the house AC being hot in the downstairs bedrooms has been fixed. The house has two brand new AC units. House was immaculate and in the perfect location with all the amenities you’d need. Only issue we ran into is the Wi-Fi does not work. They are actively working on it but the Sonos speakers did not work outside and the TVs were in and out. All in all this house had everything we needed and more
Home in Marathon
4.8 out of 5 average rating, 5 reviews

Sombrero Island Breeze 4BD Pool Retreat- M#9

JoanRating, 5 stars4 months ago
What a beautiful home! We towed our boat from northeast Florida and were thrilled with how convenient it was to drop the boat in the local marina and keep it right behind the house. Sombrero Beach was down the road and a perfect location for our grandkids to swim and play in the sand. John could not have been more helpful and responded quickly to all of my texts. We are already thinking about reserving again in the spring!
Superhost
Condo in Key Largo
4.81 out of 5 average rating, 27 reviews

Mariner's Club 535 - 4 Bedroom - THE OCEAN OASIS

KevinRating, 5 stars5 months ago
This place is beautiful, large rooms all around, clean, tastefully decorated Waking up each morning to the views overlooking the water was incredible Our group was 3 couples, never felt crowded Complex was very nice - pools, hot tub, fitness center, game room- well maintained and clean Would definitely look into seeing if this place would be available if we come down to Key Largo again. Definitely worthwhile.
Superhost
Home in Marathon
4.95 out of 5 average rating, 21 reviews

Get Hooked private pool and dock

LynnRating, 5 stars1 week ago
We recently had the pleasure of staying at a fantastic vacation rental, and it exceeded all our expectations! The house was comfortable, spacious, and perfectly equipped for a peaceful and relaxing stay. One of the highlights was the location—just a short and scenic walk to the beach, making it easy to enjoy the sound of the waves and the coastal vibe. We were also treated to the most beautiful sunrises each morning, a sight that truly made the experience unforgettable. The home was spotlessly clean, with thoughtful details that made us feel at ease. And Sheri, the host, was incredibly friendly and welcoming, ensuring every part of our stay was smooth and enjoyable. Her kindness added an individualized touch to the experience. If you’re looking for a perfect getaway with stunning views, a cozy atmosphere, and a host who genuinely cares, this place is absolutely worth considering!

Pet-friendly mansion rentals

Guest favourite
Home in Marathon
4.95 out of 5 average rating, 131 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

JenniferRating, 5 stars4 days ago
Although the place wasn’t ready when we arrived, Ryan was a great communicator! He addressed every issue we had (which were NOT within his control) and responded in a timely manner. He offered a fair solution and allowed us to sit back, relax and enjoy paradise! I’d highly recommend and hope to be back sometime soon!
Superhost
Home in Marathon
4.94 out of 5 average rating, 16 reviews

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

Stefan And KarenRating, 5 stars1 week ago
The house was spacious and clean, and we got good use out of the pool and hot tub. Bert requires signing a separate contract after booking on AirBnB, but worked with us to tailor the language. Towels are provided but be prepared to bring most other amenities like shampoo, etc yourself. Also, be aware that Sunrise Drive is a private road and you cannot access the beach there - Sombrero Beach is about a 15 minute walk, but definitely worth the walk!
Superhost
Home in Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars17 months ago
We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service
Guest favourite
Home in Key Colony Beach
4.91 out of 5 average rating, 54 reviews

*Newly Renovated Single Family Home w/Private Pool

MichaelRating, 5 stars1 week ago
The home was everything that the owner posted and more! Clean, neat and perfectly furnished. Fully stocked kitchen and all the appliances you need. Location and surroundings were beautiful. Easy walk to Sunset Park with a beautiful beach and pier. Cute shops and restaurants also in walking distance. Pool area was like a private resort. Screened in lanai was perfect for morning coffee and evening relaxation. Owners are very attentive and thoughtful. Little touches like laundry/dishwasher tabs, extra paper products, and toiletries just made it even more comfortable. Would definitely stay here again and recommend to anyone!
Guest favourite
Townhouse in Key Largo
4.93 out of 5 average rating, 73 reviews

Divers Delight with Golf Cart, 2 Kayaks, Pool

AnnaRating, 5 stars2 weeks ago
What a great condo for our group of 8! We loved being able to walk across the sidewalk to the pool and not much farther to the lagoon for beachy fun. There was enough space and privacy for our group that included kids and adults. Will totally stay again when we are in Key Largo!
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 14 reviews

Waterfront home w/pool, dock & close to beach

LaurenRating, 5 stars1 month ago
We did a couples’ trip with our three toddlers and had a wonderful stay at Ruth’s place! We had everything we needed and the location was awesome - close to beautiful Sombrero beach, restaurants, nightlife and had a dock where we could dock our rental boat. Would come back in a heartbeat!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 57 reviews

Paradise Ocean Front 4/3Home Heated Pool

BetsyRating, 5 stars3 weeks ago
We had a 5 star stay at Isabella’s Airbnb home! We had 10 guests and all had a place to sleep, place to sit and eat if we all wanted to sit together at the dining table and plenty of room there! We loved her home and our stay there!! Isabella remembered that we were there on vacation celebrating our mom’s 80th birthday and went out of her way to buy a key lime pie and balloon to have waiting for us/my mom when we arrived! That was very thoughtful and sweet of her!! Thank you for sharing your home with us!!!
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Coastal Paradise: 5-Bed Retreat

TrishRating, 5 stars2 weeks ago
We loved our latest stay in Marathon. We traveled with two families (2 teens, 2 older children). The house layout was perfect for our group. It was nice to have the kitchenette downstairs by the patio slider for pool snacks (small microwave) and clean-up from beach days/pool days. The beds were all newer, stylist beach decor, & ample space. There is lots of indoor and outdoor (covered and uncovered) table/conversation seating. The pool and hot tub were great. We spent many nights in the hot tub looking at the stars and relaxing. Although, you on a canal with other houses, it’s very quiet. The canal had fish, sharks, and even a cute manatee that visited in the morning. Our kids loved fishing daily. As for location, it’s perfect. You’re only a few miles from Sombero Beach, Sunset Beach, and 7 mile bridge. Publix, bait shops, restaurants all within a short drive. You cannot walk to beaches, but we didn’t mind this. There is a bike trail on Aviation Rd. Near the house.

Mansion rentals with a pool

Villa in Marathon
4.67 out of 5 average rating, 3 reviews

Villa Sombrero

NikkiRating, 5 stars28 months ago
We had a wonderful time. The neighborhood is beautiful, super quiet and nice to walk around. We used the provided paddle boards to go to nearby Sombrero Beach which was lovely. We also walked to Publix and Walgreens. The house itself is really two houses - one upstairs and one downstairs - each with their own kitchens, bedrooms and bathrooms. The house itself is simple and utilitarian, but backyard area is really spectacular. We spent the vast majority of our time outside lounging, playing tennis or swimming in the pool. The location also makes for an easy day trip to Key West. The property manager Jesús was extremely responsive and took care of everything we needed.
Home in Marathon
5 out of 5 average rating, 3 reviews

Canalside Cabana: Poolside Bliss with Canal Views

KeRating, 5 stars2 weeks ago
Great location! lots of funny activities within 10minutes of drive
Guest favourite
Home in Summerland Key
4.86 out of 5 average rating, 37 reviews

Powell Family Resort

AnitaRating, 5 stars11 months ago
Great property all around!! The pool was big enough for 10 people without being crowned. We utilized the kayaks, paddle boards and hammocks multiple times. The kitchen was fully stocked with everything except a blender. We even could have baked cupcakes if we wanted!! We were able to catch enough fish to have a taco night for everyone, which was an extra bonus. It was 35-40 min. to Key West, which was far enough for peace and quiet, but not too far to enjoy the fun there. We were able to walk to Kiki’s down the street, which was also nice. I would definitely recommend and stay again!
Home in Marathon
4.89 out of 5 average rating, 84 reviews

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

SofiaRating, 5 stars7 months ago
great location and great views
Home in Duck Key
4.66 out of 5 average rating, 155 reviews

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

JenniferRating, 5 stars1 month ago
Loved this place! The pool area felt very private and offered activities like corn hole and bocce ball. We had a great time!
Guest favourite
Villa in Marathon
4.88 out of 5 average rating, 57 reviews

New Paradise On Sombrero Beach

TonyaRating, 5 stars4 months ago
This place had everything we needed for a relaxing family vacation prior to the crazy Holiday season. we only had 6 people but it would easily accommodate more. Monica was responsive to any questions or concerns. The location was perfect. Easy access to sombrero Beach and Marathon amenities: bars, restaurants, and activities. we were able to experience a turtle release on Sombrero Beach from The Turtle Hospital. Highly recommend renting from Monica again and on Marathon Beach.
Home in Marathon
5 out of 5 average rating, 3 reviews

Marathon Peach Pit

ThomasRating, 5 stars9 months ago
First, Andy the owner was great. Very personable and responsive to any questions and helpful to making the trip great. The house is awesome and well furnished and very clean/new feeling. On top of a great kitchen well supplied there is an additional upright freezer for foods, ice, and most importantly lots of ice cream. There is another freezer downstairs that has left over bait from other renters that’s like a pay it forward type system. Great idea. The pool is very relaxing and lots of chairs. The location on land is right next to marathon bagel which is a bonus! Then by boat right next to vaca cut! A great benefit most don’t think about but Andy did is accommodation for the boat trailer parking. I had a 33’ trailer and a 19’ trailer and still had room for trucks. Then there are lots of water hoses and great water pressure for washing trailers and boats while there. We did mini lobster season there and had a blast! We will be back for sure!!! Tom
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 61 reviews

Luxury 4/3 Waterfront w/Private Heated Pool & Dock

PaulRating, 5 stars3 months ago
Best best best- Jorge is the absolute best. Place was great for our family of 6 and so convenient and central to everything, esp restaurants, Publix and the beach (that we biked too with bikes Jorge condo provided). A plus trip bc of his place and his incredible responsiveness and niceness. Paul

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Mansion rentals