House vacation rentals in Lower Sugarloaf Key

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Popular amenities for Lower Sugarloaf Key house rentals

House rentals with a pool

Guest favorite
An inviting open living area is featured with comfortable seating options, including a large blue sofa and patterned chairs. A flat screen TV is positioned on a wicker stand. A staircase leads to the second floor, and a dining area with a round table and rattan chairs is visible.
Home in Cudjoe Key
5 out of 5 average rating, 16 reviews

Keysie Does It at Cudjoe Key

MeganRating, 5 stars3 months ago
We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!
Guest favorite
A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.
Home in Cudjoe Key
4.98 out of 5 average rating, 47 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

KimberlyRating, 5 stars2 weeks ago
We had a great stay! House was neat and tidy and in a great location.
Guest favorite
An outdoor area features a private pool with an adjoining spa, surrounded by lounge chairs. Lush palm trees provide shade, while a spiral staircase leads to the upper level of the house. The setting offers a relaxing space for guests to enjoy.
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars1 month ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Top guest favorite
An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars3 weeks ago
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.
Superhost
A serene outdoor space includes a private pool surrounded by a spacious deck. Palm trees frame the scene, casting shadows on the white tiles. A furnished sitting area can be seen nearby, offering a relaxing spot to enjoy the warm weather.
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars3 weeks ago
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!
Superhost
A private pool is surrounded by a lush tropical garden, featuring tall palm trees and vibrant foliage. The clear water of the pool reflects the sunlight, while stone pathways and colorful blooming plants enhance the natural ambiance.
Home in Marathon
4.93 out of 5 average rating, 61 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars1 month ago
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!
Guest favorite
The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.
Home in Marathon
5 out of 5 average rating, 23 reviews

Spacious lux home, private pool/spa, 80' dock

KelliRating, 5 stars3 weeks ago
Beautiful, roomy, comfortable, well appointed home. Has absolutely everything you could need for an incredible vacation! Great little gym, really nice bikes, coolers, pool floats, beach umbrellas, kayaks and paddle boards. The entire game room area is such a great place to hang out. Good size pool, shade keeps it nice and cool. Quiet neighborhood. Owners are super responsive, very helpful. We really loved this place!
Guest favorite
A bright living area features a green sofa adorned with decorative cushions, flanked by two woven ottomans. Natural light filters through the white curtains, while a large television and colorful wall art enhance the space. Rattan accents and indoor plants bring a refreshing touch.
Home in Cudjoe Key
4.94 out of 5 average rating, 62 reviews

Betty's Place

VanessaRating, 5 stars5 days ago
We thoroughly enjoyed our stay here! The home was clean and well stocked with all we needed for a comfortable stay. The community pool was a nice plus to enjoy during this summer heat. Thanks to Jacqueline for being a great host. Would definitely stay again!

Weekly house rentals

Guest favorite
A bright living area is showcased with a sectional sofa and a round coffee table. Natural light fills the space, highlighted by decorative lamps and greenery visible through the windows. A woven rug adds texture to the wooden floor, contributing to a relaxed atmosphere.
Home in Marathon
4.96 out of 5 average rating, 25 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

CarolRating, 5 stars1 week ago
Sandra’s conch cottage was comfortable and beautiful and very clean. Provided all the necessary items for the week. The location of the house in Marathon is perfect to all amenities. I would definitely come again.
Guest favorite
An outdoor seating area features a sectional sofa and high-top bar stools with a view of the water. A peaceful ambiance is created by the surrounding palm trees and the gentle waves of Vaca Cut. Laundry facilities are visible on the left side of the image.
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!
Guest favorite
A canal-front dock features colorful adirondack chairs positioned for scenic views of the water. The surrounding area includes nearby houses and a clear blue sky, enhancing the outdoor experience. The dock provides direct access to the water, ideal for boating activities.
Home in Cudjoe Key
5 out of 5 average rating, 6 reviews

Moana Hale Paradise #164 - Venture Out, Cudjoe Key

anthonyRating, 5 stars3 months ago
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.
Superhost
A well-lit dining area features a round wooden table surrounded by six woven chairs. A decorative centerpiece is placed on the table. Adjacent, a cozy living space is visible, showcasing a sectional sofa, a ceiling fan, and large windows allowing natural light.
Home in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

Cozy 2 br/2 bath home in Cudjoe

MariannRating, 5 stars1 month ago
Marcela's place was exactly as described and very clean. One master bedroom with master bath, and another bedroom with a twin/trundle bed, and sofa in living room. Kitchen had good amenities with cutlery and glasses, etc. We didn't use the washer but the dryer was very handy for drying bath towels and pool towels. We sat outside in the back yard the first night and heard a mysterious animal call, we thought it was a bird but then using google we found out it was a tokay gecko! So cool. We used the large saltwater pool which was very very nice. It's just a short drive to several great restaurants in neighboring keys, and we made a day trip to Key West which was awesome! I recommend Tonio's Seafood Shack & Tiki Bar, great key lime pie. Forks & Stix is a great little sushi place with great lemonade, Island Fish Company in Marathon had a great outdoor vibe right on the water. Best beach is Bahia Honda State Park. Note there is a $125 community fee upon check-in to the resort.
Guest favorite
An aerial view showcases a private dock with a boat alongside a heated pool. Lounge chairs are positioned near the pool, complemented by vibrant palm trees and neatly arranged outdoor furniture. The tranquil waters reflect the bright surroundings, enhancing the overall relaxing atmosphere.
Home in Key Colony Beach
4.94 out of 5 average rating, 17 reviews

Paradise Cove!30ft Dock Pool BBQ

BryceRating, 5 stars1 month ago
Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.
Guest favorite
A sandy beachfront is framed by palm trees, with the glistening Atlantic ocean in the background. A volleyball net is set up on the sand, along with multiple seating areas for relaxation, inviting guests to enjoy the tranquil environment and scenic views.
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars3 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Guest favorite
Two yellow Adirondack chairs are situated on the sandy shore, facing a calm bay. Lush trees frame the scene, providing shade. A dock with boats is visible in the distance, under a clear blue sky dotted with a few clouds.
Home in Key Largo
4.92 out of 5 average rating, 53 reviews

Treetops

LilyRating, 5 stars3 months ago
This place was such a nice experience. The views were gorgeous and the area was peaceful. It was really a bargain for the price. I highly recommend it!
Top guest favorite
A charming outdoor space features a well-lit patio adorned with string lights. A jacuzzi hot tub and two cornhole boards are positioned on the manicured lawn surrounded by lush greenery. A quaint staircase leads to a cozy balcony overlooking the yard.
Home in Marathon
5 out of 5 average rating, 21 reviews

Serenity Oasis~Kayaks~Bikes!~Spa~HotTub!

CarrieRating, 5 stars3 days ago
We had such a wonderful trip to Marathon! This house was perfect for our family of four with plenty of room for a couple more! This place was crisp and clean! I enjoyed cooking dinner in the kitchen which was easy to get around in and very spacious! The beds in this place were so comfy and soft, the whole family enjoyed resting peacefully every night! It feels like you are on your own private island when you are in the closed in yard! It’s so private with all the lush plants surrounding the area! The hot tub was a hit as well as the game room! We played Uno and Foosball while watching tv and enjoying each other’s company! The host was also nice enough to accommodate us when we showed up to our destination an hour or so early! 10/10 would recommend!

Private house rentals

Guest favorite
A serene waterfront scene captures the reflection of clouds and colorful sunset hues on the calm water. Flanking the canal are inviting homes characterized by palm trees, with docks indicating easy access for boating enthusiasts. The peaceful setting suggests a tranquil atmosphere.
Home in Cudjoe Key
4.92 out of 5 average rating, 24 reviews

Pelican's Roost, Waterfront comfort at Venture Out

PamRating, 5 stars2 months ago
we totally enjoyed our stay. the home is spacious and has everything you would want or need for your stay. loved the screened in porch area! thank you!!!
Guest favorite
A serene view is presented from the pool area, featuring gentle waves lapping at the shore and numerous sailboats anchored in the harbor. Two palm trees provide shade, and a well-maintained lawn borders the pool, enhancing the coastal ambiance.
Home in Marathon
5 out of 5 average rating, 9 reviews

Sandbox

CretiaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ Absolute Paradise in the Heart of the Keys! Our stay at this vacation house in Marathon was nothing short of incredible. From the moment we arrived, we felt like we had found our own private slice of paradise. The house was spotless, beautifully decorated, and had all the comforts of home—plus the added bonus of breathtaking ocean views and island vibes. The location couldn’t have been better. Tucked away in a peaceful part of Marathon, we were just minutes from everything—the beach, boat rentals, amazing restaurants, and the iconic Seven Mile Bridge. The property itself was incredibly well-equipped: a fully stocked kitchen, super comfortable beds, high-speed WiFi. What really made this place stand out was the outdoor space. The private dock was perfect for fishing and sunset cocktails, and the pool made it hard to ever want to leave. We even spotted dolphins just off the dock one morning—unreal! The hosts were friendly, responsive, and went out of their way to make sure we
Top guest favorite
The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.
Home in Marathon
4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

LydiaRating, 5 stars10 months ago
We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!
Guest favorite
Three colorful adirondack chairs—one red, one yellow, and one green—are positioned on a sandy beach under palm trees. The calm blue water extends towards the horizon, while a rocky wall forms a subtle boundary in the background.
Home in Marathon
4.91 out of 5 average rating, 32 reviews

Oasis in The Keys-Kayaks-Paddle Boards-Cabana Club

LisaRating, 5 stars1 week ago
Beautiful, well appointed home in the middle of the keys within driving distance to all the tourist attractions and restaurants. We are a 3 generation trip with grandparents and kids, and this house had it all! 3 bedrooms, each with excellent ocean views, great kitchen, kayaks and bikes in the garage, and incredible outdoor seating area! Highly recommended for families.
Superhost
A spacious balcony provides unobstructed views of the Atlantic Ocean. Two white rocking chairs are positioned along the railing, allowing for relaxed seating. Bright blue skies and gentle waves create a serene coastal backdrop, enhancing the impression of open waterfront living.
Home in Marathon
4.67 out of 5 average rating, 12 reviews

P76 - Meticulous 2 bed, 2 bath home with stunning

FreidaRating, 5 stars4 months ago
The views are breathtaking!! We loved every minute we spent here. Will absolutely stay again if it’s still available.
Guest favorite
A private deck overlooks lush greenery leading to the ocean. A circular table with six chairs sits under a large umbrella, providing a shaded spot. The scene features bright blue skies and a calm sea, creating a serene atmosphere.
Home in Marathon
5 out of 5 average rating, 54 reviews

Oceanview Escape

LisaRating, 5 stars6 days ago
Marathon is hands-down the best place to stay if you want to explore the Florida Keys, and Rachel’s place couldn’t be in a better location—right in the heart of it all. We were a group of five and the house was perfect for us. It was clean, comfortable, and had everything we needed for a relaxed, easy stay. The layout gave everyone their own space, and the sleeper sofa was a great bonus—surprisingly comfortable for the kids, with what seemed to be a memory foam mattress. One of the biggest perks of the location? Herbie’s Bar and Chowder House is basically across the street—and it ended up being the best food we had during our entire week exploring the Keys. Seriously, don’t miss it. Whether we were snorkeling, kayaking, or heading to Bahia Honda or Key West for the day, everything was within easy reach. After long days out, it was great to come back to a peaceful, homey space. Rachel was a responsive and thoughtful host, and we’d absolutely stay here again. Highly recommended!
Superhost
The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Gorgeous Ocean View Home!

Ashley TaylorRating, 5 stars1 week ago
The pictures of this house, while gorgeous, do not do it justice. Not only was the house immaculate and spacious, it has the most stunning view. It is very close to shops and local beaches, and it's centered in between Key West and Islamorada. Yery, our host, was also very helpful and proactive with the one and only challenge we faced. I really can't say enough about this rental. It was spacious enough and contained all the amenities my family of seven could possibly need, including space for our dog. It has the most amazing view of the turquoise water of the Keys. It quite literally checks every box for a checklist of paradise, and I can't wait to go back!
Top guest favorite
An inviting outdoor area features a swimming pool surrounded by a manicured lawn. Comfortable lounge chairs provide ample seating, and a large umbrella offers shade. A canal with docked boats is visible in the background, complemented by palm trees swaying in the breeze.
Home in Marathon
4.98 out of 5 average rating, 56 reviews

Waterfront Heated Pool 120 ft Boat Dock

Gwen And JustinRating, 5 stars2 weeks ago
A Hidden Gem – Perfection in Every Way! Truly! This was, one of the best Airbnbs we have been to in Marathon! We have traveled down for many years and could not ask for a better place!!! From the moment we arrived, everything was absolutely perfect. The space was spotless, it slept 8 of us comfortably! Stocked with every single thing we could need! Location itself was Unbeatable! Peaceful, picturesque, and close to everything, yet somehow still felt like our own private escape! The dock cutting board and easy water hose worked perfect for any catch! The wrap around deck was the biggest hit! Seeing manatees and Tarpon sightings really made my kids day! It truly was magical experience! The pool to cool off and the mini splits in each room without it being manually controlled was the ultimate! Milton was phenomenal to communicate with! You can tell he genuinely cares about his guests♥️. Our family has already booked for next year and we highly recommend!

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