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Check prices for these dates

This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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, (1,102 reviews)
"Rooms are clean and staff is very nice! Breakfast was great also"
United States
Samantha
The price is SAR 489
SAR 551 total
includes taxes & fees
14 Oct - 15 Oct
Hampton Inn Key Largo Manatee Bay
A balcony with wicker chairs and a small table overlooking a marina with boats and palm trees.

2. 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, (1,000 reviews)
"Great hotel, we’ll be back :)"
United States
Anna
The price is SAR 571
SAR 642 total
includes taxes & fees
11 Oct - 12 Oct
Courtyard by Marriott Key Largo
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, (1,543 reviews)
"Excellent place"
United States
Manny
The price is SAR 822
SAR 1,075 total
includes taxes & fees
14 Oct - 15 Oct
Reefhouse Resort & Marina
A balcony with two white chairs overlooking a marina with boats, a building with a green roof, 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, (1,087 reviews)
"Great hotel"
United States
suany
The price is SAR 653
SAR 735 total
includes taxes & fees
21 Oct - 22 Oct
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
8.6 out of 10, Excellent, (1,855 reviews)
"Nice place to stay."
United States
Lwigy
The price is SAR 444
SAR 594 total
includes taxes & fees
14 Oct - 15 Oct
Bayside Inn Key Largo
A pool surrounded by palm trees and a beach area with lounge chairs.

6. 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 SAR 602
SAR 926 total
includes taxes & fees
21 Oct - 22 Oct
Largo Resort
A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

7. Dolphin Point Villas

Dolphin Point Villas
3.5 star property
0.7 km from Winston Waterways
9.6 out of 10, Exceptional, (525 reviews)
"Wonderful location. Great staff."
United States
Ernest
The price is SAR 391
SAR 545 total
includes taxes & fees
21 Oct - 22 Oct
Dolphin Point Villas
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, (1,871 reviews)
"Great place… recommended to anyone!!!"
United States
Francisco
The price is SAR 521
SAR 692 total
includes taxes & fees
22 Oct - 23 Oct
Marina Del Mar Resort and Marina
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, (1,499 reviews)
"i loved this place beautiful hotel full kitchen perfect for a little trip 100% recommend"
United States
Ysabella
The price is SAR 409
SAR 566 total
includes taxes & fees
18 Oct - 19 Oct
Waterside Suites & Marina
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

10. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
4.1 km from Winston Waterways
9.2 out of 10, Wonderful, (1,000 reviews)
"Very pleasant stay would recommend to anyone looking for a fun get away"
United States
Payton
The price is SAR 439
SAR 494 total
includes taxes & fees
12 Oct - 13 Oct
Sunset Cove Beach Resort
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, (905 reviews)
"This was a great place to stay"
United States
Loney
The price is SAR 508
SAR 571 total
includes taxes & fees
13 Oct - 14 Oct
Azul del Mar
A white building with a purple door, surrounded by palm trees.

12. Amoray Dive Resort

Amoray Dive Resort
2.0 star property
3.8 km from Winston Waterways
9.4 out of 10, Exceptional, (1,000 reviews)
"We enjoy our stay and will definitely come back."
United States
Ivette
The price is SAR 418
SAR 576 total
includes taxes & fees
21 Oct - 22 Oct
Amoray Dive Resort
A beach with palm trees, a dock, and a boat named "STYX".

13. 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)
"So serene and peaceful Love this place!!"
United States
Kathleen
The price is SAR 379
SAR 426 total
includes taxes & fees
22 Oct - 23 Oct
The Pelican Key Largo Cottages
An aerial view of a resort with a large pool, palm trees, and a beach.

14. 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, (1,002 reviews)
"Clean room excellent staff good location recommend"
United States
Tania
The price is SAR 987
SAR 1,318 total
includes taxes & fees
25 Oct - 26 Oct
Playa Largo Resort & Spa, Autograph Collection
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, (41 reviews)
"It was very nice!!"
United States
Michelle
The price is SAR 674
SAR 759 total
includes taxes & fees
13 Oct - 14 Oct
Kings Kamp
An aerial view of a beach resort with a dock, thatched-roof structures, and a clear blue sky.

16. Gilbert's Resort

Gilbert's Resort
2.0 star property
7.7 km from Winston Waterways
8.6 out of 10, Excellent, (1,002 reviews)
"What a great place. Rooms were very spacious for our family of 6 and you really feel in the keys with the decor. Swimming pool was nice and the little beach cove is beautiful. The deck and boats around are nice. The restaurant is very nice too. Would stay again."
United Kingdom
Anthony
The price is SAR 781
SAR 879 total
includes taxes & fees
4 Nov - 5 Nov
Gilbert's Resort
A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

17. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.2 out of 10, Wonderful, (250 reviews)
"simple breakfast, older place but clean room, access to the beach - very convenient and nice!"
United States
ANDREW
The price is SAR 440
SAR 548 total
includes taxes & fees
14 Oct - 15 Oct
Seafarer Key Largo
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

18. 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, (353 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 SAR 731
SAR 928 total
includes taxes & fees
12 Oct - 13 Oct
Kona Kai Resort and Gallery - Adults Only
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, (1,000 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 SAR 362
SAR 407 total
includes taxes & fees
18 Oct - 19 Oct
Key Largo Inn
A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

20. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
7.8 km from Winston Waterways
8.8 out of 10, Excellent, (346 reviews)
"Great place "
United States
Jay
The price is SAR 597
SAR 671 total
includes taxes & fees
21 Oct - 22 Oct
Anchorage Resort & Yacht Club
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.
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Where to stay in Winston Waterways

Find the best Winston Waterways areas and neighborhoods 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 Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby.

Silver Shores

If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit 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

Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.

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

Key Largo Village

While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jacob's Aquatic Center and Jimmy Johnson's Big Chill.

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

Cross Key Waterways

While Cross Key Waterways might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like MarineLab Undersea Laboratory and Caribbean Club Bar.

Top Winston Waterways Hotel Reviews

Drift Hotel

Drift Hotel

8/10 Good
"Clean room, comfortable bed, adequate shower. Nice that you can use kayaks, paddle boards and bicycles included in your stay. Parking convenient right in front of room. Exterior of property better maintained than inside rooms. Had to request clean towels which was slightly annoying. Need cushions for the lounge chairs as they were uncomfortably hard. Overall a decent stay for the price just not five stars nice."
Randy 6-night trip
Posted less than an hour ago
Drift Hotel

Frequently asked questions

What's it like in Winston Waterways?
You'll be sure to have fun visiting Key Largo's Winston Waterways neighborhood. Consider a visit to John Pennekamp Coral Reef State Park as part of your Winston Waterways travel plans.
How many hotels will I be able to find 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 accommodations to choose from.
If I need to cancel my hotel reservation in Winston Waterways, will I receive a refund?
Yes! The majority of hotel bookings are refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals available in Winston Waterways.
Where can I learn more about changing or cancelling my trip to Winston Waterways?
For additional details about updating your trip to Winston Waterways or cancelling it, go to https://www.expedia.com/service/.
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.