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House vacation rentals in Summerland Key

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Popular amenities for Summerland Key house rentals

House rentals with a pool

Top guest favorite
Home in Marathon
4.99 out of 5 average rating, 132 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

StephenRating, 5 starstoday
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!
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
Superhost
A spacious kitchen and dining area feature white cabinetry and a large island, providing ample food preparation space. Natural light floods the room through large windows, with a view of palm trees and the water visible in the background. Stools line the island, creating a welcoming atmosphere.
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars4 months ago
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!!!!
Guest favorite
A private pool is positioned in a landscaped yard, accompanied by an umbrella for shade. The setting features views of a canal, with boats docked nearby, complemented by tropical plants and a light-colored exterior of the duplex.
Home in Key Colony Beach
5 out of 5 average rating, 83 reviews

“La casa azul” step 3’ to a private pool

KarenRating, 5 stars2 weeks ago
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!
Superhost
A private heated pool is framed by tropical landscaping and features a shaded tiki hut nearby. Colorful inflatable rings float on the water's surface. Lounge chairs are arranged on the pool deck, offering a relaxed setting surrounded by palm trees and vibrant greenery.
Home in Summerland Key
5 out of 5 average rating, 10 reviews

Pelico Palm Villa

KellyRating, 5 stars13 months ago
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!!!
Guest favorite
A spacious living area features a large gray sectional sofa adorned with decorative cushions. A round coffee table is positioned in front, and a colorful painting of a boat enhances the wall. Natural light streams in through glass doors leading to an outdoor seating area.
Home in Marathon
4.87 out of 5 average rating, 23 reviews

Golf Coast Oasis

NoraRating, 5 stars1 week ago
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.
Superhost
Home in Key West
4.9 out of 5 average rating, 144 reviews

A Royal Escape in Key West

JoAnneRating, 5 stars2 months ago
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.
Guest favorite
A spacious dining area features a large white table surrounded by modern chairs, complemented by woven pendant lights. A comfortable sofa is situated nearby, with windows offering natural light and views of the outdoor environment. Coastal decor accents the walls, enhancing the serene atmosphere.
Home in Marathon
4.96 out of 5 average rating, 112 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JessicaRating, 5 stars1 week ago
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

Superhost
A canal-side area features a smooth concrete path bordered by gravel. Multiple chairs are arranged along the water's edge, providing views of the nearby boats and the serene canal. A staircase leads to the upper level for additional accessibility.
Home in Cudjoe Key
4.84 out of 5 average rating, 50 reviews

Keys getaway

ElizabethRating, 5 stars1 month ago
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!
Superhost
The living area showcases light-colored wood flooring and large windows offering views of the surroundings. A sectional sofa and a coffee table with a coastal design create a relaxed seating arrangement. A dining table is positioned nearby, complemented by pendant lighting.
Home in Key Colony Beach
4.74 out of 5 average rating, 23 reviews

Private Beach, Deep Water Dockage, Cabana Club

GregRating, 5 stars8 months ago
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!
Superhost
A well-appointed living area features a large wall-mounted television above a stylish console. Comfortable seating includes a pair of patterned armchairs and a light-toned sofa. Soft blue walls and a decorative chandelier enhance the airy atmosphere, while natural light streams in from the nearby entrance.
Home in Key West
4.71 out of 5 average rating, 7 reviews

Serene Lily~ Luxurious 2 bed, 2.5 bath home

RoyRating, 5 stars1 month ago
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.
Guest favorite
A tranquil canal scene is depicted, lined with palm trees and private docks. Water reflects the clear blue sky, creating a serene atmosphere. Boats are moored along the canal, showcasing direct access to Gulf and Ocean waters.
Home in Marathon
5 out of 5 average rating, 40 reviews

Yellowtail Getaway with Boat Dock and Pool 2

HopeRating, 5 stars4 weeks ago
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.
Guest favorite
A kitchen window displays a view of serene canal waters, accompanied by boats docked nearby. Decorative plants are positioned on the countertop, adding a touch of greenery. The sign above the window reads 'Marathon,' providing a local touch to the space.
Home in Marathon
4.91 out of 5 average rating, 69 reviews

Blue Ocean Bungalow Spring discounts-NOW available

HixRating, 5 stars1 month ago
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
Guest favorite
A canal dock extends alongside the property, featuring wooden decking and a swimming ladder for easy access to the water. Lounge chairs are positioned nearby, and tall palm trees provide a tropical ambiance. The clear blue sky reflects off the tranquil water.
Home in Key Colony Beach
4.91 out of 5 average rating, 135 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

NicoleRating, 5 stars3 days ago
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.
Guest favorite
The living room features an open layout with a comfortable sectional sofa and a coffee table. Light streams in through French doors, while a television is mounted on the wall. A bookshelf filled with framed artworks and decorative items adds character to the space.
Home in Key West
4.83 out of 5 average rating, 64 reviews

Historic Key West - Turtle House - Sleeps 6

BrockRating, 5 stars1 week ago
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!
Superhost
A pair of outdoor chairs is positioned on a balcony, overlooking a vibrant canal. Palm trees and neighboring homes line the waterway, while a bright sky filled with fluffy clouds enhances the serene waterfront view.
Home in Cudjoe Key
4.86 out of 5 average rating, 103 reviews

Island Oasis ~ YOUR Paradise Awaits!

PamRating, 5 stars3 weeks ago
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

Superhost
Home in Key West
4.86 out of 5 average rating, 59 reviews

Key West Paradise

BharatRating, 5 stars1 week ago
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.
Guest favorite
A modern beach house exterior features a spacious courtyard surrounded by light-colored gravel. A hot tub and shaded seating area with an umbrella are visible, along with a pergola and a cozy lounge setup. Palm trees provide a tropical backdrop, enhancing the outdoor space.
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars1 month ago
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.
Superhost
A spacious living room features tile flooring and large glass doors leading to a patio area. Comfortable seating includes a pull-out sleeper sofa and a cozy armchair. A smart television is mounted on the wall, and a wooden media console offers storage and decorative accents.
Home in Cudjoe Key
5 out of 5 average rating, 6 reviews

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

AdamRating, 5 stars1 month ago
Very clean and well maintained the property… We enjoyed our stay there. The community was very nice and very clean!
Guest favorite
A modern living area features comfortable black reclining sofas and a light-colored coffee table with woven storage underneath. A large flat-screen TV is mounted on a white media console, and vibrant turquoise walls enhance the bright and airy atmosphere.
Home in Marathon
4.98 out of 5 average rating, 91 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

RobbieRating, 5 stars1 week ago
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.
Guest favorite
Home in Key Colony Beach
4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool & Cabana Club

LauraRating, 5 stars3 months ago
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!!
Guest favorite
A view from the balcony showcases a serene canal lined with palm trees and residential homes. The water reflects the clear blue sky, creating a tranquil atmosphere. The balcony features white railings, inviting relaxation and enjoyment of the surrounding scenery.
Home in Key Colony Beach
4.95 out of 5 average rating, 42 reviews

Casa Lago Mar 3/2 with Cabana Club Access

TimRating, 5 stars3 months ago
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.
Guest favorite
A bright exterior view showcases a charming home perched on the canal's edge. Lush greenery frames the property, while a private dock extends into the water. Sunlight reflects off the calm water, and a blue sky dotted with fluffy clouds enhances the tranquil setting.
Home in Marathon
4.96 out of 5 average rating, 68 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

ChrisRating, 5 stars1 month ago
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.
Guest favorite
A bright living area features light-colored furniture arranged for comfort. A spacious sofa is paired with woven accent chairs, offering views through large glass windows overlooking a canal. Light curtains frame the windows, allowing natural light to enhance the room's open feel.
Home in Key Colony Beach
5 out of 5 average rating, 6 reviews

Key Colony Beach Waterfront 321

JeanneRating, 5 stars9 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Summerland Key
  6. House rentals