Waterfront vacation rentals in Sugarloaf Key

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Popular amenities for Sugarloaf Key waterfront rentals

Waterfront apartment rentals

Superhost
Apartment in Key Colony Beach
4.84 out of 5 average rating, 107 reviews

Beachside Unit 22 - Private Beach on Atlantic

AlexisRating, 5 stars4 days ago
Key Colony Beach is truly the gem of the Florida Keys. Staying at Cindy's apartment in the Continental was the perfect fit for my husband and I. The private beach was clean, easy to access, and just steps from the accommodation. The overall vibe here was quiet and peaceful, and the apartment had all the amenities we needed for a 5-day stay. Cindy's space is very clean and well-appointed. This location is perfect for morning walks around the immaculate and safe neighborhood, or short jaunts to Key Colony Inn or Havana Jack's for dinner/drinks. Honestly now, you're already here! What's your hurry? :)
Guest favourite
Apartment in Marathon
5 out of 5 average rating, 18 reviews

#1 Island Hideaway 89 - OCEAN FRONT

BrianRating, 5 stars2 weeks ago
Rhonda's place is terrific! Lovely location with full water views. Pool was excellent. The home was very comfortable, clean and convenient to restaurants and stores. Would definitely rent again.
Superhost
Apartment in Key West
5 out of 5 average rating, 4 reviews

Hyatt Windward Pointe! Great Location!

MelissaRating, 5 stars3 weeks ago
Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.
Superhost
Apartment in Key Largo
4.79 out of 5 average rating, 144 reviews

Escape to the Seaside!

DawnRating, 5 stars2 months ago
1st time in the keys and we stayed at Ana's lovely place for 4 days and 3 nights. It was the perfect jump off place to explore the keys. When we originally pulled up I was a little nervous as the exterior of the building is a little older and I was concerned maybe I booked something that was not as advertised, but the inside was absolutely gorgeous, better than the pictures and had everything we needed for a comfortable stay. The private beach and pier made for spectacular sunrises and sunsets, the only item to note was that the unit is upstairs and you need to hand carry your luggage to the top floor, so something to be aware of.
Superhost
Apartment in Marathon
5 out of 5 average rating, 4 reviews

Ocean Side Paradise Awaits!

JesiRating, 5 stars1 month ago
Condo was exactly as pictured. Beautiful resort and everyone very friendly onsite. Great location and close to lots to do. Cannot wait to book again.
Superhost
Apartment in Tavernier
4.89 out of 5 average rating, 65 reviews

Ocean Pointe 2309 with Ocean Views

LeeAnneRating, 5 stars3 weeks ago
An easy and relaxing family trip to the Florida Keys. Central location and a well appointed comfortable apartment. We will definitely return!
Superhost
Apartment in Key West
5 out of 5 average rating, 4 reviews

Henry's Penthouse On The Ocean

LindaRating, 5 stars4 months ago
We arrived early on the day of check-in, and because previous guests has left early, we were able to check in first thing in the morning! Henry happened to be in Key West, working around his property, so he very kindly gave us a full tour of the apartment, the parking area, the grounds, pool, and beach. The apartment is whimsically decorated with pastel colors to fit the Key West vibe, and has lots of cute details. Amazingly, all the small appliances, dishes, glasses, and tableware are in the pink/rose colored family. Literally every appliance is pink (Cuisenart, coffee maker, toaster, Keurig, blender, tableware, and more). It gave the place a unified cozy feel. The living room is spacious, with lots of couch room for a family to watch TV together. The kitchen is eat-in, and the bathrooms and bedrooms are super nice. We felt very at-home in Henry's place, and appreciate the details he provides about checking in, keys, garage parking, etc. We had a great time.
Guest favourite
Apartment in Tavernier
4.95 out of 5 average rating, 192 reviews

Boho FL Keys Condo

KevinRating, 5 stars3 days ago
The location, condo, grounds, access to restaurants and proximity to our fishing destination made this stay enjoyable. At the top of our list for our next trip.

Waterfront house rentals

Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 72 reviews

Dock, Beach Club, January avail., tennis, golf

Mary KayRating, 5 stars1 month ago
We loved our stay at Jeffery's house. It is spacious and very comfortable. My husband appreciated the proximity to the pickleball courts - we could see them from our bedroom windows- and my son enjoyed fishing off the dock. The upper suite was wonderful for privacy and quiet when the older kids stayed up later than the adults. Jeffery was super helpful and responsive. We would love to stay here again!
Superhost
Home in Islamorada
5 out of 5 average rating, 3 reviews

Islamorada Cay Home. Elegant home

MarlaRating, 5 stars1 month ago
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!
Guest favourite
Home in Key West
5 out of 5 average rating, 19 reviews

Nautical Wheeler: Waterfront Home with private Poo

KaydrianneRating, 5 stars4 months ago
The house is beautiful and well stocked. Javier provided ample information to facilitate a smooth check in process and to help my family plan for our stay. Would 100% recommend this listing to a friend!
Superhost
Home in Marathon
4.79 out of 5 average rating, 34 reviews

Luxury Waterfront Retreat with Dockage & Pool

MindyRating, 5 stars1 month ago
Had an amazing stay at this house with my husband and 4 small kids. The house was spacious and clean, with lots of natural light at soon as the sun came up. The pool was so warm and had a large shallow area that was perfect for our 3 year old. Naomi was a wonderful communicator. It was so sad to have to leave.. Would definitely recommend staying here.
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 37 reviews

Waterfront home with direct Atlantic Ocean access

MadelineRating, 5 stars1 month ago
Our first stay at this property was truly unforgettable, and we can't wait to return! Francisco is an outstanding host, always quick to respond and attentive to every detail. The house exceeded our expectations—it was spotless, fully equipped, and conveniently located near stores and restaurants. The outdoor area was a peaceful and inviting space, thoughtfully designed with a refrigerator, sink, hot tub, gas fire pit, and ceiling fans to keep you comfortable. The soft lighting added a warm and welcoming ambiance, perfect for evening gatherings or simply relaxing under the stars. We especially loved the canal, which was incredibly easy to navigate and provided quick access to the ocean—a paradise for fishing enthusiasts! We even caught fish right in the canal, but the absolute highlight was spotting manatees from the dock. If you're looking for the perfect getaway, look no further. Book your stay with Francisco—you won’t regret it
Guest favourite
Home in Key Colony Beach
4.91 out of 5 average rating, 134 reviews

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

MelissaRating, 5 stars3 weeks ago
Had a wonderful, peaceful stay. We fished off the dock area, enjoyed time at the cabana, walked every morning enjoying the views and participated in the sunset community almost every night at the park! Great vacation for our multigenerational needs!
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 25 reviews

Easy Ocean Access 30' Dock House Pool Cabana Club

DeborahRating, 5 stars3 days ago
We had an amazing week stay at this property. It was spotless with too of the line amenities. The street is very quiet with little to no traffic located at a dead end canal street. Bonus that we were able to dock our boat and it was pet friendly. The kitchen was fully stocked and we were very comfortable. We would definitely stay here again! This place is beautiful and exactly what we wanted for our week’s stay in Marathon.
Top guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 103 reviews

Waterfront House with 37 ft Dock & Cabana Club

RichardRating, 5 stars1 month ago
Great Choice in Key Colony!! We were two couples and everyone enjoyed the stay - place was immaculate, eating outside looking at the canal, watching the birds/pelicans. We did have a manatee visit one day as well. Easy drive over to Sombrero beach and many very nice restaurants around. Having access to the Cabana club and the pool was an added benefit/interest. The place does have two bathrooms which I wasn't sure of when renting. Jorge was very nice.

Waterfront condo rentals

Guest favourite
Condo in Key West
4.97 out of 5 average rating, 72 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

BrianRating, 5 stars5 days ago
Great space with everything you need. Patio is a perfect place to relax. The house is well stocked. Plenty of room for a group. Access to hotel pools/restaurant with transportation into town if you need it. Great host communication. All you could want!
Superhost
Condo in Tavernier
4.87 out of 5 average rating, 149 reviews

Reel Large END Unit in Ocean Point Suites

Suzi Rating, 5 stars2 weeks ago
The condo was well equipped and in a quiet spot. We loved the beach and didn’t have problems finding chairs. It’s not a huge beach so it wasn’t noisy or crowded. The pool is also very nice! There are beach towels, rafts and sand toys in the unit which was great. There is an area under the building with ping pong, a mini pool table and other games too. We have older kids but would’ve loved to have found this place when they were little. It’s perfect for young families with the pool and small beach. We definitely had a chance to unwind during our stay. Desy was super responsive to my questions and messages.
Guest favourite
Condo in Tavernier
4.97 out of 5 average rating, 90 reviews

Your Happy Place - Oceanfront

ChrisRating, 5 stars1 day ago
Sandra’s place was beautiful and she was a wonderful host. She was proactive in giving us all the information we needed to settle in AND also providing wonderful recommendations to restaurants around the area (three of which we tried and thoroughly enjoyed). Very responsive to any questions we had regarding locations of certain items or locations. The place itself was very cozy and homey. Felt very comfortable relaxing there in such a serene environment. Will gladly take an opportunity to stay here again.
Superhost
Condo in Marathon
5 out of 5 average rating, 10 reviews

P80 - Coral Lagoon 3bd/2.5ba townhome with large c

YuniorRating, 5 stars37 months ago
Expect a nice, relaxing time. Beautiful scenery and lots to do in Marathon Key.
Guest favourite
Condo in Tavernier
4.92 out of 5 average rating, 141 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

BrianRating, 5 stars1 week ago
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again
Top guest favourite
Condo in Tavernier
4.98 out of 5 average rating, 194 reviews

Ocean Views at Ocean Pointe

HopeRating, 5 stars2 weeks ago
Michelle was great! Very responsive and understanding when we had to make a last minute trip change. Unit was clean, bright and had a nice view. It’s a nice location between Key Largo and Islamorada making it convenient to explore both. We didn’t use any of the resort’s amenities, but there was an influx of seaweed at the small beach. Just one downside of this time of years in the Keys. But the pool looked great!
Guest favourite
Condo in Tavernier
4.84 out of 5 average rating, 149 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

TaraRating, 5 stars2 weeks ago
We had a wonderful stay! We loved spending time at the pool and on the pickleball courts. Definitely a great place for families!
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 123 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

DanelleRating, 5 stars2 weeks ago
We loved our stay at Nicole’s place. It was well stocked, super clean, and the decore was lovely. This is second time at Ocean Pointe. We enjoyed being in building 5 and the larger corner unit.

Destinations to explore