Mansion vacation rentals in Key West

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Popular amenities for Key West mansion rentals

Luxury mansion rentals

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, 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!
Top guest favourite
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 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!
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 45 reviews

Oceanfront with Pool near Sombrero Beach

JoshuaRating, 5 stars3 weeks ago
We had an amazing time at Seascape Point during our first family trip to Marathon! The home was absolutely perfect for our crew—my wife, our three kids, and me. The kids had an absolute blast hunting for crabs, fishing, and swimming all week long. The property was well-suited for our family’s needs, and it made for a memorable vacation. Thank you for helping make this trip such a great one—we’d love to come back!
Superhost
Home in Islamorada
4.84 out of 5 average rating, 25 reviews

Hidden Gem Duplex in Heart of Islamorada! Sleeps 8

SamRating, 5 stars6 months ago
This unit is near the desirable mile markers in Islamorada. Very close to the best restaurants and across the street from Islamorada Brewing Co. We also walked to Mangrove Mikes Diner for a genuine keys breakfast. Easy walk to the gulfside amenity area.
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 46 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

TrishaRating, 5 stars2 weeks ago
Eric and the home were both fantastic! Eric provides an A+ experience from the detailed guidebook before hand (including the sail instructions) to the quick communication throughout. the home itself is very nice and my kids never wanted to leave the pool!
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

Pet-friendly mansion rentals

Guest favourite
Home in Marathon
4.95 out of 5 average rating, 132 reviews

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

JenniferRating, 5 stars1 week 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 Key West
4.6 out of 5 average rating, 5 reviews

Coastal Comfort; Waterfront Luxury Home with priva

JayRating, 5 stars18 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
Top guest favourite
Home in Marathon
4.95 out of 5 average rating, 22 reviews

Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool

DawnRating, 5 stars6 months ago
We had ten guests who enjoyed our stay at our Marathon air bnb! We very much enjoyed the pool- we used it every day and loved being right on the canal for fishing and manatee spotting! The home was equipped with enough bathrooms so many can be in use at once, the beds were comfortable and it was very spacious. We also enjoyed the outdoor enclosed patio and the little tiki hut for another shaded option. We had an iguana who stayed right out front during our stay and he was very peaceful. Kitchen was equipped with all appliances needed to cook throughout the week including a grill! We had a great time and felt safe during our stay! Will definitely book with Jay in the future!!
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 stars2 weeks 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!
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
4.97 out of 5 average rating, 58 reviews

Paradise Ocean Front 4/3Home Heated Pool

DustinRating, 5 stars3 weeks ago
Great place to stay! I would come back. was hoping to see manatees but you can't control nature. Great set up for. families with kids.
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Coastal Paradise: 5-Bed Retreat

TrishRating, 5 stars3 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.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 37 reviews

Dock Pool Home by Sombrero Beach

CorinneRating, 5 stars1 month ago
Really nice location. Pool heated very nicely for young children (which we paid for.) Frank was responsive to the things we needed.

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 stars3 weeks ago
Great location! lots of funny activities within 10minutes of drive
Guest favourite
Condo in Key Largo
4.9 out of 5 average rating, 30 reviews

Mariner's Club 126 - A SEA DWELLERS PARADISE 4 BR

AnnetteRating, 5 stars2 months ago
Susies home was perfect for our family vacation. Comfortable, lovely views and well located within the complex.
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 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
Home in Key West
4.89 out of 5 average rating, 37 reviews

Millionaire Row Heart of Key West 4 BR Resort Home

ChristieRating, 5 stars1 month ago
Great location, quiet and comfortable. Penny was very responsive when we had a question. Very comfortable house plenty of room for the 5 of us. I have a Bronco and it was a tight fit back in carport with 5 bikes but we made it work. Thank you Penny for sharing your home with us.
Guest favourite
Home in Marathon
4.83 out of 5 average rating, 6 reviews

Sombrero Island Breeze 4BD Pool Retreat- M#9

EricRating, 5 stars3 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 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

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