Holiday houses in West Summerland Key

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Top-rated holiday rentals in West Summerland Key

Guests agree: these stays are highly rated for location, cleanliness and more.

Superhost

Townhouse in Marathon

4.81 out of 5 average rating, 42 reviews

Beachy Townhome Perfect For A Warm Winter Getaway!

DougRating, 5 stars1 month ago
We enjoyed our getaway. The property met our expectations from the listing. Great locations to enjoy the Keys. Megan was easy to communicate with and helpful!
Guest favourite

Cottage in Marathon

4.96 out of 5 average rating, 27 reviews

Catch n' Relax Canalfront Cottage in Marathon

JodiRating, 5 stars2 months ago
Great location. It was so nice having our boat slip right in front of the house. Tastefully decorated and close to a lot of activities. We enjoyed the Dolphin Research Center, Turtle Hospital, Crane Point being so close that we biked using bikes is at the house! 😀
Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

Sunrise Beach Escape

WinslowRating, 5 stars9 months ago
We had a wonderful stay, there was plenty of room for our family of 4 (5- and 7-year-old kids). We trailered a small boat and the marina/docks were fantastic, exploring the area via boat was a breeze. We wouldn't hesitate to book again!
Guest favourite

Apartment in Marathon

5 out of 5 average rating, 11 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

BrianRating, 5 stars1 month ago
Very clean, great location Will definitely rent again
Guest favourite

Home in Marathon

5 out of 5 average rating, 23 reviews

Waterfront Escape -VACA-23-408

RebeccahRating, 5 stars3 days ago
We had such a great time and there was plenty to do. The house and amenities were even more beautiful than the photos. We loved being on the Chanel and seeing manatees right off the dock!
Guest favourite

Home in Marathon

5 out of 5 average rating, 21 reviews

Direct Oceanfront Private Paradise - Pool/Spa/Dock

HannaRating, 5 stars1 week ago
I have stayed in many AirBnbs—and this was, by far, the best. We chose to visit Marathon for our family vacation. Our family includes our parents, and 3 adult couples, all with different relaxation styles. This location had something for everyone, so we could "choose our own adventure" easily—whether it was a kayak adventure, fishing right in the backyard, yoga on the sandy beach area, relaxing in the hot tub, catching a football game on the outdoor TV, and puzzling or playing board games on the spacious outdoor table! We loved exploring the city of Marathon, especially the Dolphin Research Center, scuba / snuba diving locally, and all the great happy hours with fresh seafood! The home was clean, spacious, and private. The hosts were responsive and above-and-beyond generous (we even arrived to a welcome basket of goodies and thank you card!). If we're lucky, this won't be the last time we get to stay in this wonderful home!
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 16 reviews

Venture Out- Million Dollar Island Resort

TerriRating, 5 stars3 months ago
Only issue we had was getting in the community. The security did not have us on the list. BUT that was resolved with one phone call. Everything was great. Could not have had a better. Location. Quiet community. Beautiful pool. Little store. Perfect!
Guest favourite

Home in Marathon

4.9 out of 5 average rating, 71 reviews

Dream Vacation KCB Marathon with private pool !

RyanRating, 5 stars6 months ago
This place is truly a gem perfect for a couple or a family very worth the price for the location and the place location is private with a very clean pool overall everything is great if you have the opportunity to book this place I definitively recommend getting it
Superhost

Cottage in Cudjoe Key

4.65 out of 5 average rating, 108 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

DonnaRating, 5 stars2 months ago
in the photographs the pool looked closer to our Airbnb. other than that everything was just perfect. Jason responded right away to any questions I had and made it very easy. I would recommend his place to anyone. thank you so much
Guest favourite

Home in Marathon

5 out of 5 average rating, 29 reviews

Amazing Bayfront Newer House with Dock and Pool!

DachaRating, 5 stars1 month ago
We had a great week at Mike’s place and appreciate him kindly accommodating our stay last minute. The house & property is so beautiful, everything looks brand new and was extremely clean. We enjoyed fishing from the dock and lying by the pool. The house has all amenities needed to cook meals, including an air fryer, toaster and also a blender for frozen drinks. Pool supplies are well stocked, as well as beach chairs. We would love to stay again! Thank you so much!
Superhost

Home in Marathon

5 out of 5 average rating, 5 reviews

Gated w/Bayside Marina- Marlin Bay Resort & Marina

JenRating, 5 stars37 months ago
Beautiful property with all the comfort of home! Very clean and organized. This was the perfect location and home for our family of 5. We have a 17, 15 and 9 year old, lots of entertainment for all the kids! Best family vacation ever!
Guest favourite

Home in Cudjoe Key

4.86 out of 5 average rating, 14 reviews

Blue Vacation Home. Free cancellation policy

RachelRating, 5 stars2 weeks ago
Terrific vacation location!!! Mitch and Lu (and Richie) were the absolute best hosts, sharing favorite local spots, tips, and tricks. The location is beautiful and private, yet close to everything, and the house has everything you could need! Would definitely recommend this property and we cannot wait to spend another week here!

Popular amenities for West Summerland Key holiday rentals

Other great holiday rentals in West Summerland Key

Guest favourite

Guesthouse in Marathon

4.94 out of 5 average rating, 18 reviews

The Pink Dolphin House.

ScottRating, 5 stars1 week ago
We absolutely loved Margaret's place! It was picturesque and so fun! We loved the view, the pool, the local restaurants and her home felt very comfortable for my family of five. Thank you Margaret and Phil!!!
Guest favourite

Home in Cudjoe Key

5 out of 5 average rating, 27 reviews

Paradise in Cudjoe! Perfect Family Home!

JordanRating, 5 stars3 months ago
Taylor and Kali were friendly and polite. Very accommodating and the location was perfect. Loved having the space to filet fish and easy access to open water. Would def recommend!
Guest favourite

Villa in Marathon

4.95 out of 5 average rating, 127 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

StephanieRating, 5 stars1 week ago
Isabel’s place was the perfect spot for my family’s vacation. The house has everything you need for cooking, sleeping and having fun. My kids are all adults and they loved the bikes, kayaks, paddle boards and corn hole. My daughter and her boyfriend were on the paddle board when a manatee and her baby swam right next to them! The location is great for the grocery store and beach. It was truly perfect.
Guest favourite

Home in Cudjoe Key

4.93 out of 5 average rating, 45 reviews

Private Ocean Oasis by Key West, Florida

DonnaRating, 5 stars1 month ago
This was the perfect place to meet up for a Christmas gathering with our adult children. The home was so nicely decorated and furnished and had EVERYTHING we could have needed for a three day stay. There was plenty to do on the Venture Out Resort property and anything else you’d want or need is within driving distance. Will definitely stay here again!
Guest favourite

Home in Marathon

4.9 out of 5 average rating, 168 reviews

Beachfront Villa - Florida Keys

AshleyRating, 5 stars5 months ago
This house is remarkable. Not only does it have the most spectacular view, and welcoming yard. The beach is literally right across the street. Absolutely gorgeous. This house comes with everything that you might need. Lots of dishes, lots of towels, lots of extra blankets and pillows! They offered a welcome package with all the items that you may have forgotten. We were very pleased and enjoyed our stay so much.
Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 10 reviews

Sleeps 8, 3 bedroom, 4 full bath, pool, 37.5' dock

JeffreyRating, 5 stars4 months ago
Excellent location in a quiet upscale neighborhood. The house was like new, everything was clean and fresh. Very well equipped kitchen and baths. Lots of space indoors and out, with a beautiful small pool! Would definitely recommend this property for a peaceful getaway in the heart of the Florida Keys!!!
Superhost

Townhouse in Marathon

4.95 out of 5 average rating, 21 reviews

Waterfront luxury Villa (29) with sunset views and boat slip

CarissaRating, 5 stars42 months ago
Couldn’t have imagined a better stay, view, location, convenience for our boat up staycation. It was perfection! Bonus, balcony overlooking the canal doubled as my yoga studio!!
Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 6 reviews

Cielo's Del Mar 2 - Pool/Dock/Beach Luxury in KCB

AprilRating, 5 stars9 months ago
Perfect for our trip. The house had everything we needed and then some. We would stay again.

Destinations to explore