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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 stars1 day ago
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!!!!
Superhost
A light-filled living area features a soft blue sofa and an armchair. A round woven coffee table occupies the center, while two stylish lamps provide illumination. The open layout connects to a fully equipped kitchen, with glimpses of adjacent bedrooms visible through doorways.
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars1 week ago
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!
Superhost
A heated swimming pool is featured in a wooden deck area, surrounded by tropical palm trees. Lounge chairs are positioned for relaxation, while the exterior of the two-story home includes expansive glass doors that provide a view of the inviting pool and canal.
Home in Islamorada
4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

JessicaRating, 5 stars7 months ago
I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.
Top 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!
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.
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!
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.
Superhost
The living area showcases a blend of vibrant colors, with green and orange walls that create a cheerful atmosphere. A cozy sofa adorned with decorative pillows faces a coffee table, while a well-equipped kitchen is visible in the background, enhanced by bright natural light from multiple windows.
Home in Key West
4.6 out of 5 average rating, 15 reviews

Tranquility by AvantStay | Close to Duval St

ChristianRating, 5 stars2 months ago
Wonderful location in Key West. The cottage & neighborhood was very quiet and was walkable to essentially the entire island. Very good value compared to other lodging options in the area!
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 stars4 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.
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
4.87 out of 5 average rating, 104 reviews

Island Oasis ~ YOUR Paradise Awaits!

AbbyRating, 5 stars2 weeks ago
Bonnie was a nice, responsive host and even brought us additional kayaks to use. We had a great stay!
Guest favorite
A spacious screened-in porch features a large dining table surrounded by teal chairs, complemented by ceiling fans. Sunlight filters through the screens, showcasing views of the canal with palm trees and boats visible in the background, creating a relaxing outdoor space.
Home in Marathon
4.97 out of 5 average rating, 35 reviews

Marathon 3BR Canal Pool Spa Special WK May 4-11

MattRating, 5 stars1 day ago
Great peaceful place to stay. We saw manatees, tarpon and many other species in the canal. Also had some short visits from different types of lizards and iguanas. The pool and hot tub were amazing everyone in our group enjoyed them. The dock was a great place to keep our rental boat. I would 100% come back.

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.
Top guest favorite
An open living area showcases a modern design with white wood beams and bright walls. A dark granite countertop separates the dining area from the lounge, furnished with blue seating and a flat-screen TV. Large glass doors provide views of the outdoor space.
Home in Key Colony Beach
5 out of 5 average rating, 44 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars1 day ago
Perfect for our family of 5. Great outdoor area at the house for fishing and relaxing. The layout was great for us because of the separation from the master to the kitchen/living room…our baby could sleep and we didn’t have to worry about making noise and waking up the baby. KCB is in a great central location for exploring the Keys. We were also pleasantly surprised at the quality of restaurant’s nearby. The Cabana Club was crowded and has a small beach. Drinks there were good. I have nothing overly negative to say, other than that I wouldn’t look to stay in KCB or this property if you just want to hang at the pool and beach all day. But it was fine for a few easy afternoons between other activities in the area. We highly recommend and would stay again!
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 at 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.

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