Hotels in Winston Waterways

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top 10 Hotels in Winston Waterways

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
8.8 out of 10, Excellent, (1002)
"Love the placw"
The price is S$476
includes taxes & fees
2 Dec - 3 Dec
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Playa Largo Resort & Spa, Autograph Collection
4.5 star property
8.8 out of 10, Excellent, (1000)
"We had an amazing time at the resort, I love all of the different activities designed for families. The bartenders and all the staff were so friendly and welcoming. Definitely a recommended place for either a staycation or a time away from the everyday."
The price is S$541
includes taxes & fees
8 Dec - 9 Dec
Playa Largo Resort & Spa, Autograph Collection
The Pelican Key Largo Cottages
2.0 star property
8.6 out of 10, Excellent, (1001)
"Great staff, rooms and area"
The price is S$189
includes taxes & fees
1 Dec - 2 Dec
The Pelican Key Largo Cottages
Rock Reef Resort
2.5 star property
9.2 out of 10, Wonderful, (1002)
"Wonderful owner and staff, thank you Miss Linda and Ashley. "
The price is S$204
includes taxes & fees
24 Nov - 25 Nov
Rock Reef Resort
Reefhouse Resort & Marina
3.5 star property
9.2 out of 10, Wonderful, (1208)
"Great property- beautiful view of you have the right balcony room. "
The price is S$343
includes taxes & fees
15 Dec - 16 Dec
Reefhouse Resort & Marina
Bayside Inn Key Largo
3.0 star property
8.6 out of 10, Excellent, (1377)
"We enjoyed staying at Bayside. It was conveniently located and perfect for our needs. The staff was very friendly and helpful. I did notice the floors of our room needed mopping as they made our feet dirty which we noticed when we stepped into the shower. We would stay there again."
The price is S$212
includes taxes & fees
25 Nov - 26 Nov
Bayside Inn Key Largo
Sunset Cove Beach Resort
2.5 star property
8.8 out of 10, Excellent, (1003)
"Beautiful property. Even though they were doing some work, everyone was respectful and quiet. The only hiccup was that parking at times was tight as someone tried to park in our spot and another parked so close to our door we almost hit the car walking just trying to get past to our door. Overall super peaceful and plenty of seating by the beach. A few not so clean things like the inside of my shower curtain was dirty and a floor board was a tad loose and moved if you walked on it and the remote...
The price is S$235
includes taxes & fees
8 Dec - 9 Dec
Sunset Cove Beach Resort
Marina Del Mar Resort and Marina
2.5 star property
8.2 out of 10, Very good, (1206)
"Great location for the views! Off the main road so it wasn't that loud. Beds were great, pillows, so-so. "
The price is S$121
includes taxes & fees
3 Dec - 4 Dec
Marina Del Mar Resort and Marina
Holiday Inn Key Largo, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (1002)
"Right along marina with excursions available "
The price is S$212
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Key Largo, an IHG Hotel
Hampton Inn Key Largo Manatee Bay
2.5 star property
8.6 out of 10, Excellent, (1006)
"Would recommend this to anyone coming down."
The price is S$226
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Key Largo Manatee Bay
Drift Hotel
2.5 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful property, very clean and friendly staff"
The price is S$179
includes taxes & fees
27 Nov - 28 Nov
Drift Hotel
Waterside Suites & Marina
3.5 star property
8.6 out of 10, Excellent, (1001)
"Nice property, good pool."
The price is S$223
includes taxes & fees
5 Dec - 6 Dec
Waterside Suites & Marina
Kona Kai Resort and Gallery - Adults Only
2.5 star property
9.8 out of 10, Exceptional, (211)
"Charming relaxed ambiance. Understated luxury. A real gem. "
The price is S$290
includes taxes & fees
22 Nov - 23 Nov
Kona Kai Resort and Gallery - Adults Only
Amoray Dive Resort
2.0 star property
8.8 out of 10, Excellent, (1001)
"Fantastic stay"
The price is S$180
includes taxes & fees
2 Dec - 3 Dec
Amoray Dive Resort
Azul del Mar
3.5 star property
9.0 out of 10, Wonderful, (617)
"There were other couples staying there but they never were at the beach so it felt like we had rhe whole resort to ourselves. It was so quite and peaceful. We even saw manatees and a stingray from the dock one morning. "
The price is S$189
includes taxes & fees
27 Nov - 28 Nov
Azul del Mar
Courtyard by Marriott Key Largo
3.0 star property
8.0 out of 10, Very good, (1000)
"Liked location, access to restaurant, parking in garage. Didn’t like the fact that anyone could access the hotel elevator from garage without a key card. Should have another layer of security. "
The price is S$204
includes taxes & fees
10 Dec - 11 Dec
Courtyard by Marriott Key Largo
Gilbert's Resort
2.0 star property
8.6 out of 10, Excellent, (1000)
" Good "
The price is S$253
includes taxes & fees
24 Nov - 25 Nov
Gilbert's Resort
Key Largo Inn
3.0 star property
6.4 out of 10, (1000)
"under renovation but rooms remain tired. More a value motel than a hotel. Very limited breakfast but coffee was good. Several places around to eat and drink, best was Mrs Moe's (both venues)."
The price is S$224
includes taxes & fees
24 Nov - 25 Nov
Key Largo Inn
Dolphin Point Villas
3.5 star property
9.6 out of 10, Exceptional, (388)
"Excellent"
The price is S$289
includes taxes & fees
2 Dec - 3 Dec
Dolphin Point Villas
Largo Resort
3.0 star property
9.6 out of 10, Exceptional, (251)
"Couldn’t have dreamed of a better place to end our trip. We were looking for peace, serenity, and quiet and this is exactly what Key Largo Resort offers! Special thanks to Dayana that welcomed us and made sure that we enjoyed our stay in the best way possible. Until next time ! "
The price is S$477
includes taxes & fees
15 Dec - 16 Dec
Largo Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Winston Waterways
Save an average of 15% on thousands of hotels when you're signed in
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What's it like in Winston Waterways?

You'll be sure to have fun exploring Key Largo's Winston Waterways neighbourhood. Consider a visit to John Pennekamp Coral Reef State Park as part of your Winston Waterways travel plans.

What's a favourite hotel to stay in Winston Waterways?

For your stay in Winston Waterways, Cukoos Nest by Florida Keys Luxury Rentals is one of the top choices based on our traveller data.

How many hotels are there in Winston Waterways?

With 19 Expedia hotels and other accommodation options in Winston Waterways to choose from, this is a good starting point for exploring the greater Key Largo area.

If I need to cancel my hotel reservation in Winston Waterways, will I receive a refund?

Yes! The majority of room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to view top deals in Winston Waterways.

What are the top things to see and do in Winston Waterways?

John Pennekamp Coral Reef State Park is an attraction you might want to check out while you're in Winston Waterways. When you're sightseeing in Key Largo, Lower Sound Point and MarineLab Undersea Laboratory are also worth a stop.