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Check prices for these dates

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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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, (1,124 reviews)
"Great stay"
United States
Joliene
The price is ฿4,402
฿4,952 total
includes taxes & fees
29 Nov - 30 Nov
Hampton Inn Key Largo Manatee Bay
A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.

2. Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
2.9 km from Winston Waterways
9.2 out of 10, Wonderful, (1,559 reviews)
"Beautiful property, great room, perfect location. Staff were amazing and very nice clean property! Restaurant was excellent"
Canada
William Dean
The price is ฿7,384
฿9,656 total
includes taxes & fees
29 Nov - 30 Nov
Reefhouse Resort & Marina
A balcony with wicker chairs and a small table overlooking a marina with boats and palm trees.

3. 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, (1,002 reviews)
"Great hotel, we’ll be back :)"
United States
Anna
The price is ฿5,128
฿5,769 total
includes taxes & fees
9 Nov - 10 Nov
Courtyard by Marriott Key Largo
A reception area with a wooden ceiling, tiled floor, and a reception desk with a floral design.

4. 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, (1,074 reviews)
"Great hotel"
United States
suany
The price is ฿5,529
฿6,221 total
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Key Largo by IHG
Two hands holding wine glasses with a beach and ocean view in the background.

5. Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
3.9 km from Winston Waterways
8.4 out of 10, Very good, (1,865 reviews)
"This is a lovely place and I would happily stay here again."
United States
joseph g
The price is ฿3,655
฿4,955 total
includes taxes & fees
4 Nov - 5 Nov
Bayside Inn Key Largo
A balcony with a view of the sea, a beach, and a thatched hut.

6. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.2 out of 10, Wonderful, (1,007 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is ฿4,096
฿4,609 total
includes taxes & fees
29 Nov - 30 Nov
Sunset Cove Beach Resort
A multi-story hotel with balconies, palm trees, and a view of the water.

7. 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, (1,858 reviews)
"Great place enjoyed the stay"
United States
Dawn
The price is ฿4,317
฿5,805 total
includes taxes & fees
17 Nov - 18 Nov
Marina Del Mar Resort and Marina
A waterfront property with multiple buildings, a dock, and a small island with palm trees.

8. Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (532 reviews)
"Excelente place for couples and the whole family"
United States
Hansel
The price is ฿4,366
฿5,860 total
includes taxes & fees
8 Nov - 9 Nov
Dolphin Point Villas
A balcony with a view of the sea, a table, and two chairs.

9. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,517 reviews)
"Just a quick stay but was very comfortable."
United States
Bryan
The price is ฿4,132
฿5,597 total
includes taxes & fees
4 Nov - 5 Nov
Waterside Suites & Marina
A white building with a purple door, surrounded by palm trees.

10. Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.8 km from Winston Waterways
9.4 out of 10, Exceptional, (1,007 reviews)
"This place was awesome. Location, staff, property itself, all was excellent. Absolutely would come back and would highly recommend"
United States
Rodrigo
The price is ฿2,756
฿4,049 total
includes taxes & fees
4 Nov - 5 Nov
Amoray Dive Resort
A pool surrounded by palm trees and a beach area with lounge chairs.

11. Largo Resort

Largo Resort
3.0 star property
0.9 km from Winston Waterways
9.4 out of 10, Exceptional, (320 reviews)
"Excelente"
United States
Olbert
The price is ฿6,846
฿9,939 total
includes taxes & fees
12 Nov - 13 Nov
Largo Resort
A beach with a thatched-roof hut, lounge chairs, and a swimming area.

12. 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, (1,006 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is ฿3,366
฿3,787 total
includes taxes & fees
23 Nov - 24 Nov
The Pelican Key Largo Cottages
A balcony with a view of the ocean and palm trees.

13. Azul del Mar

Azul del Mar
3.5 star property
3.8 km from Winston Waterways
9.0 out of 10, Wonderful, (914 reviews)
"This was a great place to stay"
United States
Loney
The price is ฿5,037
฿5,667 total
includes taxes & fees
1 Dec - 2 Dec
Azul del Mar
A covered outdoor area with a pool, palm trees, and a wooden deck.

14. Key Largo Inn

Key Largo Inn
3.0 star property
4.5 km from Winston Waterways
6.6 out of 10, (1,001 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 ฿3,611
฿4,063 total
includes taxes & fees
15 Nov - 16 Nov
Key Largo Inn
A wooden bridge leading to a beach area with palm trees and a yellow kayak.

15. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.2 out of 10, Wonderful, (263 reviews)
"This may be my favorite place I've stayed in the Keys! So quaint and the location and breakfast were amazing. We kayaked to the mangroves, ate at the wonderful restaurant across the street (Ballyhoos), and thoroughly enjoyed the beach area"
United States
Brittany
The price is ฿4,141
฿5,133 total
includes taxes & fees
4 Nov - 5 Nov
Seafarer Key Largo
A tropical resort with a clear pool, palm trees, and lounge chairs.

16. 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, (365 reviews)
"We will make this an annual trip. A great place. Thank you for making it a great stay"
United States
Billy
The price is ฿4,799
฿6,348 total
includes taxes & fees
4 Nov - 5 Nov
Kona Kai Resort and Gallery - Adults Only
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

17. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,202 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is ฿3,045
฿3,425 total
includes taxes & fees
15 Nov - 16 Nov
Rock Reef Resort
A beachfront property with a wooden building, outdoor seating, and palm trees.

18. 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 ฿10,165
฿11,436 total
includes taxes & fees
17 Nov - 18 Nov
Kings Kamp
A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

19. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
7.8 km from Winston Waterways
8.8 out of 10, Excellent, (352 reviews)
"Very clean Nice staff"
United States
Doris
The price is ฿5,361
฿6,031 total
includes taxes & fees
17 Nov - 18 Nov
Anchorage Resort & Yacht Club
An aerial view of a resort with a large pool, palm trees, and a beach.

20. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor, 7.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,004 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is ฿8,867
฿11,834 total
includes taxes & fees
29 Nov - 30 Nov
Playa Largo Resort & Spa, Autograph Collection
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

Compare popular hotels in Winston Waterways

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A beach with palm trees, lounge chairs, and a clear view of the ocean.
Hampton Inn Key Largo Manatee Bay
2.5 star property
8.8
Excellent
1,124 reviews
View
A dining area with tables set for two, overlooking a beach with palm trees and a sunset view.
Reefhouse Resort & Marina
4.5 star property
9.2
Wonderful
1,559 reviews
View
A waterfront property with multiple buildings, a dock, and a small island with palm trees.
Dolphin Point Villas
3.5 star property
9.6
Exceptional
532 reviews
View
A pool surrounded by palm trees and a beach area with lounge chairs.
Largo Resort
3.0 star property
9.4
Exceptional
320 reviews
View
A white building with a purple door, surrounded by palm trees.
Amoray Dive Resort
2.0 star property
9.4
Exceptional
1,007 reviews
View

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.

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.

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.

Anglers Park

If you're looking for some top things to see and do in Anglers Park and surrounding area, you can visit MarineLab Undersea Laboratory and Caribbean Club Bar.

Top Winston Waterways Hotel Reviews

Rock Reef Resort

Rock Reef Resort

8/10 Good
"A peaceful cozy space in Key Largo perfect place to come and enjoy the sunset and clear your mind. Checking in and checking out are straightforward, but the staff can be a little pushy during the checkout process to meet that 11 AM deadline."
S 2-night trip
Posted 7 hours ago
Rock Reef Resort

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.