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House vacation rentals in Sugarloaf Key

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Popular amenities for Sugarloaf Key house rentals

House rentals with a pool

Top guest favorite
Home in Marathon
4.99 out of 5 average rating, 133 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

MauraRating, 5 stars3 days ago
We had an incredible week at Eddie’s place! The listing description and pictures matched our experience. Our favorite places to hang out were the screened in area, Tiki Hut, and by the dock. We fished off the dock daily and caught a great number of fish! We were also visited by a manatee. Eddie’s place is easily walkable to Sombrero Beach. The kitchen was well stocked and had everything we needed! We truly enjoyed this beautiful spot and would definitely book again on a future stay!
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
Guest favorite
A bright and airy living area is highlighted by large glass doors that lead to the outdoors. White slipcovered furniture complements the coastal decor. A wooden console table displays decorative items and a television is mounted on the wall opposite the seating area.
Home in Marathon
4.89 out of 5 average rating, 63 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

BarbaraRating, 5 stars3 weeks ago
You won’t find a better set up than this with family. Playground, beach, pool , sidewalks for walking everywhere, and great kayaking area as well. And the owner makes sure his guests have all they need.
Guest favorite
Home in Key Largo
4.94 out of 5 average rating, 70 reviews

Casa Solaris | Key Largo home with Private Pool!

JessicaRating, 5 stars2 days ago
My family had a wedding in Key Largo and wanted a nice space to hold 6 people with a private pool. This place matched our needs perfectly! It's incredibly spacious, has amazing amenities and of course had the most beautiful pool and spa. I loved how there was a separate downstairs area with a kitchenette so my husband and I could have extra space as well. It was also close distance to restaurants and grocery stores. Sean always answered quickly and offered help if we ever needed it. It was the perfect house for our little getaway.
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
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 stars3 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 spacious living area features comfortable seating arrangements, including a striped sofa and recliner. A light wood coffee table sits atop a decorative area rug. The open layout allows visibility to the dining area and kitchen, enhancing togetherness in the inviting home.
Home in Key Colony Beach
4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

BrittanyRating, 5 stars31 months ago
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.

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, 51 reviews

Keys getaway

JamiRating, 5 stars2 weeks ago
We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁
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 stars9 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 stars1 month 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 stars2 weeks 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
A quaint exterior displays a historic house with a metal roof and a bright blue flag. Lush green foliage is seen throughout the property, complemented by a white picket fence that adds charm and outlines the front yard.
Home in Key West
4.83 out of 5 average rating, 64 reviews

Historic Key West - Turtle House - Sleeps 6

BrockRating, 5 stars2 weeks 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
4.87 out of 5 average rating, 104 reviews

Island Oasis ~ YOUR Paradise Awaits!

AbbyRating, 5 stars3 weeks ago
Bonnie was a nice, responsive host and even brought us additional kayaks to use. We had a great stay!

Private house rentals

Superhost
Home in Key West
4.87 out of 5 average rating, 61 reviews

Key West Paradise

BryanRating, 5 stars1 week ago
Very convenient location for our scheduled golf outing and fishing trips! Just a short distance to old town KW for all the crazy fun, which meant we got to leave the noise behind when we were ready to relax and just spend time with the family on the large back porch and the pool. The place was very clean and felt like home to us for the week that we spent there. Thank you to Sharon for everything.....my entire family is already asking when are we coming back!!!!
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.
Guest favorite
A renovated house is set on a corner lot, surrounded by palm trees and coral stone landscaping. The exterior features light yellow walls and white accents. A gravel driveway offers ample parking space, complementing the tranquil tropical environment.
Home in Marathon
4.92 out of 5 average rating, 136 reviews

Marathon Star - home with hot tub

MichaelRating, 5 stars3 weeks ago
good location, clean and quiet. Close to shopping and restaurants and attractions.
Guest favorite
A charming entrance is framed by lush tropical foliage and vibrant flowers. Bright blue doors welcome guests, set against a backdrop of crisp white siding and welcoming porch. A white picket fence adds an inviting touch, blending harmoniously with the surrounding greenery.
Home in Key West
4.9 out of 5 average rating, 70 reviews

Casa Loca

ElizabethRating, 5 stars2 months ago
Casa loca was Absolutely beautiful! So close to everything in the keys. Host super friendly and helpful. The house was very clean! 10/10 stay LOVED IT!
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 stars2 weeks 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 stars4 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
Home in Key Colony Beach
4.95 out of 5 average rating, 112 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

JessRating, 5 stars2 weeks ago
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!
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, 69 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.

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