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Check prices for these dates

This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

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Our top choices for Winston Waterways hotels

A beach with palm trees, lounge chairs, and a clear view of the ocean.

1. Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
0.6 km from Winston Waterways
8.8 out of 10, Excellent, (1,094 reviews)
"The property was clean and the staff very polite"
United States
Ruddy
The price is ฿4,334
฿4,875 total
includes taxes & fees
5 Oct - 6 Oct
Hampton Inn Key Largo Manatee Bay
A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

2. Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (519 reviews)
"The place was great - just like the photos and central to everything. The restaurant across the street, called the Catch, ended up being our best meal of the trip. The kayaks were really fun and the place was really nice."
United States
Michael
The price is ฿4,072
฿5,516 total
includes taxes & fees
23 Sept - 24 Sept
Dolphin Point Villas
A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.

3. Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
2.9 km from Winston Waterways
9.4 out of 10, Exceptional, (1,542 reviews)
"Resort was great"
United States
Susan
The price is ฿6,614
฿8,771 total
includes taxes & fees
27 Sept - 28 Sept
Reefhouse Resort & Marina
A balcony with a view of the sea, a table, and two chairs.

4. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,489 reviews)
"The place was clean, and the staffs were nice and helpful. We enjoyed our staying."
United States
Thuc
The price is ฿4,073
฿5,517 total
includes taxes & fees
23 Sept - 24 Sept
Waterside Suites & Marina
A balcony with wicker chairs and a small table overlooking a marina with boats and palm trees.

5. Courtyard by Marriott Key Largo

Courtyard by Marriott Key Largo
3.0 star property
3.4 km from Winston Waterways
8.2 out of 10, Very good, (1,001 reviews)
"Everyone was so helpful and friendly"
United States
Jennifer
The price is ฿4,756
฿5,351 total
includes taxes & fees
28 Sept - 29 Sept
Courtyard by Marriott Key Largo
A balcony with two white chairs overlooking a marina with boats, a building with a green roof, and palm trees.

6. Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG
3.0 star property
3.6 km from Winston Waterways
8.6 out of 10, Excellent, (1,092 reviews)
"Great hotel"
United States
suany
The price is ฿5,351
฿6,020 total
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn Key Largo by IHG
A pool surrounded by palm trees and a beach area with lounge chairs.

7. Largo Resort

Largo Resort
3.0 star property
0.9 km from Winston Waterways
9.4 out of 10, Exceptional, (319 reviews)
"The rooms are amazing for the price. Everything is clean. It was very quiet and family friendly"
United States
Tara
The price is ฿5,729
฿9,025 total
includes taxes & fees
11 Oct - 12 Oct
Largo Resort
A multi-story hotel with balconies, palm trees, and a view of the water.

8. Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina
2.0 star property
3.5 km from Winston Waterways
8.6 out of 10, Excellent, (1,870 reviews)
"Great place… recommended to anyone!!!"
United States
Francisco
The price is ฿4,543
฿6,045 total
includes taxes & fees
6 Oct - 7 Oct
Marina Del Mar Resort and Marina
A white building with a purple door, surrounded by palm trees.

9. Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.8 km from Winston Waterways
9.2 out of 10, Wonderful, (1,003 reviews)
"This property was clean and the staff was very friendly. It is a cozy little get away in Key Largo with nice restaurants close by. Would definitely stay again."
United States
P
The price is ฿2,769
฿4,050 total
includes taxes & fees
23 Sept - 24 Sept
Amoray Dive Resort
Two hands holding wine glasses with a beach and ocean view in the background.

10. Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
3.9 km from Winston Waterways
8.6 out of 10, Excellent, (1,851 reviews)
"Nice place to stay."
United States
Lwigy
The price is ฿3,835
฿5,145 total
includes taxes & fees
23 Sept - 24 Sept
Bayside Inn Key Largo
A balcony with a view of the ocean and palm trees.

11. Azul del Mar

Azul del Mar
3.5 star property
3.8 km from Winston Waterways
9.0 out of 10, Wonderful, (895 reviews)
"This is the most incredible vacation spot we have ever experienced. Thankful we found just in time for our Honeymoon. We enjoyed all the amieties & the surrounding ones as well. The ease of check-in & check-out was great."
United States
Luann
The price is ฿3,696
฿4,158 total
includes taxes & fees
27 Sept - 28 Sept
Azul del Mar
A floating house with a thatched roof, large sliding glass doors, and a wooden deck with a chair.

12. Premium Floating Bungalow by Stay Ombi

Premium Floating Bungalow by Stay Ombi
3.5 star property
2.4 km from Winston Waterways
9.6 out of 10, Exceptional, (4 reviews)
"Great experience ! Will do it again"
United States
Deivys
The price is ฿27,349
฿30,768 total
includes taxes & fees
23 Sept - 24 Sept
Premium Floating Bungalow by Stay Ombi
A beach with thatched umbrellas, lounge chairs, and a clear view of the ocean.

13. Kings Kamp

Kings Kamp
2.5 star property
2.6 km from Winston Waterways
8.6 out of 10, Excellent, (41 reviews)
"It was very nice!!"
United States
Michelle
The price is ฿6,701
฿7,538 total
includes taxes & fees
23 Sept - 24 Sept
Kings Kamp
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

14. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,186 reviews)
"Absolutely lovely resort, we always have a wonderful stay ♥️"
United States
Tia
The price is ฿3,080
฿3,464 total
includes taxes & fees
23 Sept - 24 Sept
Rock Reef Resort
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

15. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.2 out of 10, Wonderful, (1,009 reviews)
"Very pleasant stay would recommend to anyone looking for a fun get away"
United States
Payton
The price is ฿3,889
฿4,375 total
includes taxes & fees
24 Sept - 25 Sept
Sunset Cove Beach Resort
A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

16. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.2 out of 10, Wonderful, (241 reviews)
"simple breakfast, older place but clean room, access to the beach - very convenient and nice!"
United States
ANDREW
The price is ฿3,334
฿4,218 total
includes taxes & fees
23 Sept - 24 Sept
Seafarer Key Largo
An aerial view of a beach resort with a dock, thatched-roof structures, and a clear blue sky.

17. Gilbert's Resort

Gilbert's Resort
2.0 star property
7.7 km from Winston Waterways
8.6 out of 10, Excellent, (1,005 reviews)
"We stayed for two nights that enjoyable stay. The views from a room are beautiful. The people working there were very kind. Food was quality very good, relaxing atmosphere. We definitely go back."
United States
Rick
The price is ฿6,955
฿7,824 total
includes taxes & fees
23 Sept - 24 Sept
Gilbert's Resort
A beach with palm trees, a dock, and a boat named "STYX".

18. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
4.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,002 reviews)
"Great place great price great location "
United States
Richard
The price is ฿3,236
฿3,641 total
includes taxes & fees
27 Sept - 28 Sept
The Pelican Key Largo Cottages
A covered outdoor area with a pool, palm trees, and a wooden deck.

19. Key Largo Inn

Key Largo Inn
3.0 star property
4.5 km from Winston Waterways
6.6 out of 10, (1,002 reviews)
"Staff is the Best, Owner is very friendly, forget about those nonsense reviews, this place is very nice to stay"
United States
Rolando
The price is ฿3,111
฿3,500 total
includes taxes & fees
23 Sept - 24 Sept
Key Largo Inn
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

20. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.8 out of 10, Exceptional, (352 reviews)
"Kona Kai is truly amazing!! Best staff ever!! Grounds are gorgeous and everything well kept up. Rooms are immaculate. Definitely would go back!!"
United States
Karen
The price is ฿4,210
฿5,671 total
includes taxes & fees
24 Sept - 25 Sept
Kona Kai Resort and Gallery - Adults Only
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.
View all properties

Where to stay in Winston Waterways

Find the best Winston Waterways areas for the activities you enjoy most.
A beachside resort with lounge chairs, a thatched-roof hut, and palm trees.
Photo by Samantha Shoemaker
Open Photo by Samantha Shoemaker

Rock Harbor

While there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Silver Shores

While there might not be top attractions in Silver Shores, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Harry Harris Park.

An aerial view of a coastal area with RVs parked along the shore, a small beach, and a clear view of the ocean.

Key Largo Park

Key Largo Park might not have many top sights, but Jacob's Aquatic Center and Jimmy Johnson's Big Chill are two attractions nearby that you can check out.

A white speedboat on a blue ocean with a tropical island in the background.

Key Largo Village

When in Key Largo Village, you can plan a visit to Jacob's Aquatic Center and Jimmy Johnson's Big Chill, some noteworthy sights in the nearby area.

A bridge over a river with boats docked along the shore.

Cross Key Waterways

When in Cross Key Waterways, you can plan a visit to MarineLab Undersea Laboratory and Caribbean Club Bar, some noteworthy sights in the nearby area.

Top Winston Waterways Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"This place feels like paradise! It is so calm and relaxing yet vibrant and fun. We had amazing weather all weekend. The ocean was so nice. The poolside trivia, scavenger hunt, smores and silent disco were so fun. The live music was a hit! We cannot WAIT to come back soon!"
Pilar 2-night trip
Posted 2 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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.
How many hotels are there in Winston Waterways?
If you're searching for places to stay in Key Largo, Expedia has something to meet your needs with 22 Winston Waterways hotels and other accommodation options to choose from.
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, Newport Flats and Lower Sound Point are also worth a stop.