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
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 stars1 week ago
We had a great stay! House was neat and tidy and in a great location.
Top guest favorite
An outdoor space features a sparkling in-ground pool surrounded by a sun deck with several lounge chairs. A shaded screened-in porch is visible in the background, along with a gas grill and a cornhole game set nearby. Lush palm trees provide a tropical atmosphere.
Home in Marathon
4.99 out of 5 average rating, 137 reviews

Cancellation Deal: 08/02 thru 08/09

KevinRating, 5 stars1 week ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Guest favorite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.
Superhost
A spacious living area includes a comfortable sofa adorned with decorative pillows, a coffee table, and dining space. Natural light filters through large windows, illuminating contemporary artwork on the walls. The open layout leads to a well-equipped kitchen visible in the background.
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
A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.
Home in Marathon
4.89 out of 5 average rating, 66 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

RobinRating, 5 stars2 weeks ago
This home is even more than the pictures show! It is an extraordinary home for people who love the sun, shade, beach, and the beautiful home just makes it a luxurious vacation. I could not find one aspect I didn’t love.❤️
Superhost
A vibrant green house is presented with large windows adorned with yellow shutters. A spacious front porch is bordered by tropical plants, while a gravel pathway leads to the entrance. Nearby, a blue trash bin is visible, along with a parked vehicle.
Home in Cudjoe Key
4.79 out of 5 average rating, 19 reviews

Tropical Island Getaway

DebraRating, 5 stars2 months ago
Place was sweet, kitchen and bathroom well stocked. We didn’t get an opportunity to try the pool or hot tub. 20 minutes to Key West!! We would stay there again.
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 stars2 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!
Guest favorite
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
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars3 weeks 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!!!

Weekly house rentals

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 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 resort-style swimming pool is surrounded by lush palm trees, offering a relaxing atmosphere. Comfortable lounge chairs are positioned around the pool, with tranquil ocean views in the background. Clear blue skies complement the serene setting, suggesting an inviting space for leisure.
Home in Islamorada
5 out of 5 average rating, 18 reviews

Pristine pool front home w/ocean views Anglers 148

LindsayRating, 5 stars5 months ago
We recently had the pleasure of staying at this amazing beachfront house, and I can confidently say it exceeded all of my expectations! The location is simply perfect—just steps away from the water ideal for morning walks or sunrise views. The property itself is comfortable, with stylish and easy interiors that make it feel like a home away from home. The highlight was the pool—perfectly maintained and surrounded by lush greenery, offering a peaceful oasis to relax in when you want a break from the ocean. Whether you’re lounging by the pool with a book or enjoying a refreshing swim, it’s a great place to unwind. The host was also incredibly welcoming and provided thoughtful touches, from local recommendations to ensuring we had everything we needed for a great stay. I highly recommend this property for anyone looking to enjoy a relaxing beach getaway with the added luxury of a pool. Can’t wait to return!
Guest favorite
A cozy outdoor seating area features two wicker chairs and a matching loveseat, adorned with blue-patterned cushions. A wooden coffee table sits at the center, accompanied by a decorative lantern. The setup is positioned on a covered porch overlooking the canal.
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Sea Turtle Cove

ThomRating, 5 stars1 month ago
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.
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, 22 reviews

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

HeatherRating, 5 stars1 month ago
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!
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 stars2 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Top guest favorite
A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.
Home in Key West
5 out of 5 average rating, 19 reviews

Funky Chicken Cottage with Shared Pool

LincolnRating, 5 stars1 week ago
Thank you soo much for hosting us Irene! We truly appreciate you having us. We had an amazing Key West! You were a wonderful host. I’d definitely recommend anyone book here!
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!

Private house rentals

Top guest favorite
The exterior of a charming waterfront home is depicted, showcasing a canal with clear turquoise water. Lush palm trees frame the property, and well-maintained landscaping adds to the serene environment. The two-story building features a spacious porch and multiple balconies, enhancing outdoor living.
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

ReneeRating, 5 stars3 days ago
Wonderful Stay! Place was super clean and nicely decorated with minimal decor. (Sometimes places are over decorated and busy) Beach Towels were provided. Kitchen was organized & clean. Pool was nice! We brought our small dogs and the grounds were very pet friendly. Jessica’s recommended list of restaurants was spot on! Had a great time eating at several of the places. Would visit again and recommend to others.
Guest favorite
A modern two-story home features a clean white exterior with navy blue accents. A set of black stairs leads to a covered balcony adorned with potted plants. Large windows allow natural light to enter, while a gravel driveway provides ample space in front.
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars1 week ago
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.
Superhost
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, 8 reviews

Sandbox

MikeRating, 5 stars3 months ago
The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.
Superhost
A private pool and jacuzzi are surrounded by a grassy area, with colorful lounge chairs positioned nearby. The view captures the serene waterway and neighboring properties under a bright sky, offering a peaceful outdoor setting.
Home in Marathon
4.85 out of 5 average rating, 26 reviews

Dock Pool Ramp Jacuzzi Ocean Views Kayaks

WillRating, 5 stars1 month ago
This stay was the perfect vacation I was looking forward to, I stayed 7 days at this water front property with a great balcony to enjoy evenings and a boat ramp to launch the boats in the back yard along with the pool to keep us cool. Plenty of room for our trucks and trailers, the inside of the home was comfortable and relaxing. Was truly a great vacation Thank you
Top guest favorite
A private pool is situated beside a spacious deck, surrounded by tropical plants and palm trees. Comfortable lounge chairs are placed near the pool, and stairs lead to the upper level of the stilted structure. The area offers direct access to the canal.
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars3 weeks ago
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!
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 stars2 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 serene waterway is shown, flanked by palm trees and waterfront homes. A boat is seen navigating the calm waters, with clear skies enhancing the tranquil scene. The reflection of the surroundings is visible on the surface, creating a peaceful atmosphere.
Home in Cudjoe Key
4.62 out of 5 average rating, 165 reviews

Ocean Front Home in Great Location

MichaelRating, 5 stars1 month ago
Fantastic place for a home base while the beautiful keys. Close enough to key west for an upbeat day, very quiet in the evening. If anything, I’d say I was expecting less from the description and was very surprised at how nice this place is. I would stay here again in a heartbeat!
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 stars2 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.

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