
House vacation rentals in Summerland Key
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Top-rated house rentals in Summerland Key
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Popular amenities for Summerland Key house rentals
House rentals with a pool

Sea Ray Cove, Mini Lobster week NOW OPEN!
We had a great time during our one week stay. The location was perfect! Easy walk to the beach and beautiful canal views. We loved our visits from the manatee! We spent our days outside exploring the Keys and it was lovely to return each evening to this great house. We grilled dinners and enjoyed meals on the screened porch. Sunrise over the canal was gorgeous. We were sad to leave!

Coastal Comfort; Waterfront Luxury Home with priva
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

Serenity Bay Estate-FL Keys Best Kept Secret! Beau
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!

“La casa azul” step 3’ to a private pool
We throughly enjoyed our stay. We especially loved the private pool and watching the wildlife and boaters in the canal. It was very relaxing and the Florida spring weather was awesome!

Pelico Palm Villa
This home was absolutely beautiful!! It was exactly what we had hoped for, We were a family of 4 with my husband and I, with are two sons, ages 17 & 20, plus ones girlfriend age 16. We wanted a nice family vacation without the spring break chaos & this was it! This home was so clean yet cozy, had all the necessities we needed, everyone had their own room and bathroom which was super!!! This home could definitely accomodate so many more if you wanted to do so. We were the only ones there at the time, so we had the pool area to ourselves which we loved sooooo much! We played bags by the pool daily, swam during day & at night. The home had a great deck with a wonderful grill, we made slushy drinks with the ninja blender, anything you wanted this place had! We traveled to Key West a couple times which was nice and close, about a 30 minute drive. All in all this place is top notch! Don't hesitate to book! It's worth it!! LOVED this Home!! & Nate was a spectacular host!!!

Golf Coast Oasis
We really enjoyed our week at Gulf Coast Oasis! The house was lovely, well-stocked, and great for our family of 5. We very VERY much enjoyed the pool and appreciated being able to heat it. Loved using the bikes and kayaks. Ate on the screened in porch. Madelyn was very helpful and responsive both in advance of and during our trip. Great stay! The only "negative" was the noise from the nearby airport -- not disruptive but worth noting.

A Royal Escape in Key West
Perfect for out family. We enjoyed the pool and sat out on the deck quite a bit. Enjoyed our breakfast outside. It was close to many places. The host was super responsive to any issues we had. Highly recommend. Thank you for comfortable place to enjoy.

Anglers Terrace, Condé Nast Traveler's Best Airbnb
Our family of 9 loved the house! The pool, corn hole, and roof deck were all huge hits with the kids. The house is perfectly situated on Marathon, close to all the restaurants. Quick drive to Bahia Honda. We will definitely will be back for another visit to Andy’s place.
Weekly house rentals

Keys getaway
House was perfect for my family of 3- including my 15 month old. There was some trouble with the AC thermostat at first but Jana was very responsive and immediately took care of it. We walked to Morning Joint and My New Joint/Square Grouper. My son loved the pool. All neighbors were super friendly, as well as security guards. The grill was perfect for dinner at home one night and the kitchen was fully stocked!

Private Beach, Deep Water Dockage, Cabana Club
Roberto is by far the most thorough and conscientious host. We were so pleased with our accommodations and immediately felt at home. The use of The Cabana Club was a real bonus on the hottest days. Will most certainly return to Marathon!

Serene Lily~ Luxurious 2 bed, 2.5 bath home
Beautiful home and we enjoyed our stay. We felt right at home and the pool was a nice walk. The kitchen had anything you would need to make a meal. We will definitely come back again. Thank you.

Yellowtail Getaway with Boat Dock and Pool 2
We absolutely loved the place , it was spacious , clean and had all the extras you would need. So convenient with the boat dick and loved having the pool. Would definitely return.

Blue Ocean Bungalow Spring discounts-NOW available
The house was really nice, clean and a real home away from home. It accommodated my family of 5 with 3 bedrooms and 3 baths. It was located on a canal where we were able to enjoy the manatees and pelicans. It was centrally located and only a short distance from the beaches, snorkeling, wind surfing and excellent restaurants. We will definitely stay again if we visit the keys

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
We didn't know anything about Key Colony so based our reservation strictly on reviews and price. Well worth every penny that was spent. What a wonderful tropical getaway! Can't wait to visit the Keys again with my 4 children and husband. If you're looking for a great place to spread out and enjoy family this should be your rental.

Historic Key West - Turtle House - Sleeps 6
Turtle house was great and as advertised. It was well furnished and clean. The location was perfect, so close to great restaurants and shopping. The grounds were beautiful and well maintained. I would definitely stay here again and recommend to anyone traveling to Key West!

Island Oasis ~ YOUR Paradise Awaits!
As soon as we walked in we felt right at home. We were celebrating my 65th bday week.Bonnie even had me a bday cake in the freezer .Power was destined to be out for several hours one day they brought us a small plug and play generator to run coffee pot hair dryer etc. My only disappointment was we could not use the Kayak's due to the sludge in the canal. That was not any fault of Bonnie or Joe's just mother nature. We had the pleasure of meeting the awesome host and hostess very nice people indeed. Loved their home and hospitality. If we ever come back will stay here again. Very comfortable bed. Clean and comfortable very relaxing.Nice resort and amenities very nice pool.
Private house rentals

Key West Paradise
Sharon was an excellent host that answered any of our questions promptly. The place was even better than what the photos showed. Comfortable enough for 7 people to stay for a long weekend. We didn't use the pool, but it was nice to have the option. Easy to get into the gated community, and we didn't struggle to find parking with our rental car. Easy to get to many different popular spots around Key West with rideshare. Convenient to have some convenience stores like CVS within walking distance, and a Publix not too far via car. Only thing I would improve is having more toilet paper and hand soap refills in each bathroom, especially with 7 people staying over a long weekend.

Seaside Sunrise. Newly remodeled waterfront
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Very clean and well maintained the property… We enjoyed our stay there. The community was very nice and very clean!

4BR 3B, Heated Pool & Spa, 60' Dock
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.

Waterfront House - 30' Dock & Pool & Cabana Club
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!

Casa Lago Mar 3/2 with Cabana Club Access
We loved staying at Melissa’s Airbnb. The neighborhood was nice and very walkable. Loved being right on the canal. The Cabana Club was great for kids with the pool and beachfront area. Marathon was a great Key to stay on with lots to do. The duplex was clean and beds were comfortable. Loved sitting out on the back porch in the morning with coffee. We would definitely recommend and would love to come back someday.

Private 174ft Dock, Boat Launch, Sombrero Beach
We had a great stay here, beds were comfortable and bathrooms were clean. Kids loved fishing off the dock - although the boat ramp was unavailable, we were able to use the ramp at the marina down the block ($30 each drop). Hosts were easy to communicate with and very helpful when we had a question. Wed definitely stay here again next time in Marathon.

Key Colony Beach Waterfront 321
Great place right in the heart of Key Colony. House had all we needed and more to make our 8 day stay comfortable. Great boat dock with plenty of room for 2 31 ft boats.
Quick stats about house rentals in Summerland Key
Total rentals
210 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
150 properties have a pool
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