Search Hotels in Winston Waterways, Key Largo

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Check prices for these dates

Tonight
8 Nov - 9 Nov
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9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 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, (1,130 reviews)
"Great stay"
United States
Joliene
The price is ฿4,378
฿4,925 total
includes taxes & fees
16 Nov - 17 Nov
Hampton Inn Key Largo Manatee Bay
A beach with thatched umbrellas, palm trees, and blue lounge chairs.

2. Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
2.9 km from Winston Waterways
9.2 out of 10, Wonderful, (1,565 reviews)
"Very nice property, rooms were well appointed, oceanside fire pit was a nice touch."
Canada
Vince
The price is ฿7,351
฿9,612 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 ฿4,803
฿5,404 total
includes taxes & fees
30 Nov - 1 Dec
Courtyard by Marriott Key Largo
A pool with a rock feature, lounge chairs, and palm trees.

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, (1,075 reviews)
"Great hotel"
United States
suany
The price is ฿5,505
฿6,193 total
includes taxes & fees
11 Nov - 12 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, (1,861 reviews)
"This is a lovely place and I would happily stay here again."
United States
joseph g
The price is ฿3,822
฿5,139 total
includes taxes & fees
8 Dec - 9 Dec
Bayside Inn Key Largo
A marina with boats docked along a waterfront, surrounded by buildings and palm trees.

6. Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,528 reviews)
"Just a quick stay but was very comfortable."
United States
Bryan
The price is ฿4,113
฿5,571 total
includes taxes & fees
10 Nov - 11 Nov
Waterside Suites & Marina
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

7. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.2 out of 10, Wonderful, (1,002 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is ฿4,078
฿4,588 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.

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, (1,853 reviews)
"Great place enjoyed the stay"
United States
Dawn
The price is ฿4,330
฿5,815 total
includes taxes & fees
9 Nov - 10 Nov
Marina Del Mar Resort and Marina
A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

9. 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 ฿4,347
฿5,834 total
includes taxes & fees
11 Nov - 12 Nov
Dolphin Point Villas
A beachside seating area with two white Adirondack chairs and a small table under a thatched roof structure.

10. Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.8 km from Winston Waterways
9.4 out of 10, Exceptional, (1,001 reviews)
"Location,staff was incredible"
United States
Kansas
The price is ฿2,160
฿3,374 total
includes taxes & fees
9 Nov - 10 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, (321 reviews)
"Excelente"
United States
Olbert
The price is ฿7,801
฿11,004 total
includes taxes & fees
15 Nov - 16 Nov
Largo Resort
A beach with palm trees, a dock, and a boat named "STYX".

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, (1,007 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is ฿3,351
฿3,770 total
includes taxes & fees
29 Nov - 30 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, (917 reviews)
"This was a great place to stay"
United States
Loney
The price is ฿3,897
฿4,384 total
includes taxes & fees
9 Nov - 10 Nov
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, (1,000 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 ฿3,595
฿4,045 total
includes taxes & fees
10 Nov - 11 Nov
Key Largo Inn
A beach with thatched umbrellas, lounge chairs, and a clear view of the ocean.

15. Kings Kamp

Kings Kamp
2.5 star property
2.6 km from Winston Waterways
8.6 out of 10, Excellent, (42 reviews)
"It was very nice!!"
United States
Michelle
The price is ฿10,120
฿11,385 total
includes taxes & fees
10 Nov - 11 Nov
Kings Kamp
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, (265 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 ฿2,892
฿3,725 total
includes taxes & fees
19 Nov - 20 Nov
Seafarer Key Largo
An aerial view of a resort with a large pool, palm trees, and a beach.

17. 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, (1,003 reviews)
"Everything was amazing!!! Beautiful hotel and great location."
United States
Jorge
The price is ฿8,828
฿11,781 total
includes taxes & fees
29 Nov - 30 Nov
Playa Largo Resort & Spa, Autograph Collection
A covered outdoor area with a view of a beach and palm trees.

18. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,206 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is ฿3,031
฿3,410 total
includes taxes & fees
15 Nov - 16 Nov
Rock Reef Resort
A beach with lounge chairs and a pier extending into the water.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
8.3 km from Winston Waterways
8.8 out of 10, Excellent, (1,200 reviews)
"Very relaxing the beach was nice and pretty from that side of the property clean rooms staff was nice and helpful they made the stay enjoyable"
United States
Damion
The price is ฿8,834
฿11,789 total
includes taxes & fees
29 Nov - 30 Nov
Baker's Cay Resort Key Largo, Curio Collection by Hilton
A beach with palm trees, a thatched-roof structure, and kayaks.

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, (368 reviews)
"We had a great stay. Nice, cosy, and clean. Very quiet, which we loved. Great views from the dock. We will be back!"
Canada
Daniel
The price is ฿6,314
฿8,047 total
includes taxes & fees
10 Nov - 11 Nov
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

Compare popular hotels in Winston Waterways

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.
Dolphin Point Villas
3.5 star property
9.6
Exceptional
532 reviews
View
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
1,130 reviews
View
A beachside seating area with two white Adirondack chairs and a small table under a thatched roof structure.
Amoray Dive Resort
2.0 star property
9.4
Exceptional
1,001 reviews
View
A marina with boats docked along a waterfront, surrounded by buildings and palm trees.
Waterside Suites & Marina
3.5 star property
9.0
Wonderful
1,528 reviews
View
A beach with thatched umbrellas, palm trees, and blue lounge chairs.
Reefhouse Resort & Marina
4.5 star property
9.2
Wonderful
1,565 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

A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.
Dolphin Point Villas

Dolphin Point Villas

Dolphin Point Villas
Key Largo

10/10 Excellent

Beautiful cannot fault.
United Kingdom
Sarah-Jane
Reviewed April 30, 2026
Dolphin Point Villas

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.