Hotels in Winston Waterways, Key Largo

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winston Waterways hotels

Treasure Harbor

Treasure Harbor
3.0 star property
24 km from Winston Waterways
9.0 out of 10, Wonderful, (153 reviews)
"Amazing stay!"
United States
Amanda
The price is CA $219
CA $437 total
includes taxes & fees
May 12 - May 13
Treasure Harbor

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor, 6.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,127 reviews)
"Had a great stay just what we wanted "
Canada
Elizabeth
The price is CA $241
CA $271 total
includes taxes & fees
May 13 - May 14
Rock Reef Resort

Largo Resort

Largo Resort
3.0 star property
0.9 km from Winston Waterways
9.4 out of 10, Exceptional, (308 reviews)
"Smelled a little musty."
United States
Nicholas
The price is CA $235
CA $476 total
includes taxes & fees
Jun 1 - Jun 2
Largo Resort

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (173 reviews)
"The breakfast was fresh and delicious. The room was clean and spacious. The property was tidy and had a great feel. "
United States
Kristen
The price is CA $188
CA $231 total
includes taxes & fees
May 20 - May 21
Seafarer Key Largo

Drift Hotel

Drift Hotel
2.5 star property
10.7 km from Winston Waterways
9.0 out of 10, Wonderful, (1,006 reviews)
"Great family atmosphere definitely will be back again "
United States
ELIO
The price is CA $240
CA $285 total
includes taxes & fees
May 25 - May 26
Drift Hotel

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)
"Great location and very nice staff!! "
United States
Yuliet
The price is CA $201
CA $226 total
includes taxes & fees
Jun 2 - Jun 3
Sunset Cove Beach Resort

Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
24.2 km from Winston Waterways
9.6 out of 10, Exceptional, (246 reviews)
"Nicely decorated and clean room with excellent common areas on property. Great location as well."
United States
Janet
The price is CA $268
CA $302 total
includes taxes & fees
May 7 - May 8
Ragged Edge Resort & Marina

Waterside Suites & Marina

Waterside Suites & Marina
3.5 star property
3.2 km from Winston Waterways
9.0 out of 10, Wonderful, (1,328 reviews)
"Great stay for our short trip"
United States
jesica
The price is CA $174
CA $234 total
includes taxes & fees
May 31 - Jun 1
Waterside Suites & Marina

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)
"Very clean, friendly staff, excellent bar and beach. Saw lots of marine life"
United States
Jennifer
The price is CA $265
CA $298 total
includes taxes & fees
May 26 - May 27
Gilbert's Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
28.6 km from Winston Waterways
9.2 out of 10, Wonderful, (1,714 reviews)
"Perfect place to stay and a super friendly and helpful staff...definitely staying here again"
United States
Nathan
The price is CA $243
CA $351 total
includes taxes & fees
May 11 - May 12
Chesapeake Beach Resort

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, (1,006 reviews)
"Good breakfast bar and nice bayside location."
United States
tom cochran
The price is CA $195
CA $219 total
includes taxes & fees
Jun 1 - Jun 2
Hampton Inn Key Largo Manatee Bay

Bay Harbor Lodge

Bay Harbor Lodge
3.0 star property
Rock Harbor, 6.7 km from Winston Waterways
9.4 out of 10, Exceptional, (686 reviews)
"So grateful to have chosen this little gem for our first visit to the Keys. Look forward to staying again soon"
United States
Andrea
The price is CA $266
CA $299 total
includes taxes & fees
May 6 - May 7
Bay Harbor Lodge

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, (312 reviews)
"The facility was in great shape and had everything we wanted. Nice pool, included kayaks, beautiful views, etc. Staff was super friendly and gave great advice regarding local eateries. Can't wait to stay again!"
United States
Joseph W
The price is CA $280
CA $353 total
includes taxes & fees
May 6 - May 7
Kona Kai Resort and Gallery - Adults Only

Key Largo Inn

Key Largo Inn
3.0 star property
4.5 km from Winston Waterways
6.6 out of 10, (1,006 reviews)
"Great stay for the money and area"
United States
Eileen
The price is CA $170
CA $191 total
includes taxes & fees
May 10 - May 11
Key Largo Inn

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, (1,773 reviews)
"Excellent Views and so much to do around the area. "
United States
shane
The price is CA $172
CA $232 total
includes taxes & fees
May 10 - May 11
Marina Del Mar Resort and Marina

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, (1,004 reviews)
"Very clean property with beach access and super comfortable beds!!"
United States
Anthony
The price is CA $170
CA $191 total
includes taxes & fees
May 26 - May 27
The Pelican Key Largo Cottages

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
26.5 km from Winston Waterways
8.2 out of 10, Very good, (1,002 reviews)
"Amazing hotel"
United States
robertocarlos
The price is CA $184
CA $251 total
includes taxes & fees
Jun 4 - Jun 5
Fisher Inn Resort & Marina

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
14.2 km from Winston Waterways
8.4 out of 10, Very good, (1,011 reviews)
"There was construction going on at the building they booked us in, which was a bit bothersome but not entirely. The room was comfortable, the beach area and pool were enjoyable. Good spot for families."
United States
Beth
The price is CA $208
CA $258 total
includes taxes & fees
May 6 - May 7
Ocean Pointe Suites at Key Largo

Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
7.8 km from Winston Waterways
8.8 out of 10, Excellent, (328 reviews)
"The room was clean and the views from our rooms were amazing!!!"
United States
Elizabeth
The price is CA $266
CA $299 total
includes taxes & fees
May 7 - May 8
Anchorage Resort & Yacht Club

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
3.9 km from Winston Waterways
8.6 out of 10, Excellent, (1,731 reviews)
"Loved the seating by the beach to watch the sunset and the easy access to the restaurant/bar next door."
United States
Stephen
The price is CA $178
CA $234 total
includes taxes & fees
May 10 - May 11
Bayside Inn Key Largo
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.

Where to stay in Winston Waterways

Find the best Winston Waterways areas and neighborhoods for the activities you enjoy most.

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.

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 Jimmy Johnson's Big Chill and Jacob's Aquatic Center.

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 Pigeon Key.

Key Largo Park

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

Pirates Cove

While Pirates Cove might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Top Winston Waterways Hotel Reviews

Frequently asked questions

What other neighbourhoods are similar to Winston Waterways?
When considering areas similar to Winston Waterways, we'd recommend looking at the Marina District or Downtown for their comparable offerings and atmosphere.

The Marina District, situated just south of Winston Waterways, offers a similar waterfront experience with a focus on leisure and dining. It's characterised by its extensive boardwalks, dotted with cafes and restaurants offering views of the yachts and boats. The area is particularly appealing to couples looking for a relaxed yet sophisticated getaway, with opportunities for sunset cruises and waterside dining.

Downtown, while not directly on the water, provides a similar upscale urban experience with a focus on convenience and high-quality amenities. It's known for its well-maintained streets, boutique shops, and a variety of gourmet restaurants.
What are the best hotels in Winston Waterways that travellers recommend?
Three of the best hotels in Winston Waterways that receive consistently high recommendations from travellers are Dolphin Point Villas, Largo Resort, and Hampton Inn Key Largo Manatee Bay.

The 3.5-star Dolphin Point Villas, with an exceptional 9.6 rating, offers spacious rooms and amazing suites with premium bedding, air conditioning, and deep soaking bathtubs. Guests frequently comment on the friendly staff and the beautiful sunsets visible from the property. The villas also boast a private beach and private pools, and are conveniently located near John Pennekamp Coral Reef State Park.

Largo Resort, a 3-star property with a 9.4 rating, provides a wonderful experience with its private beach, ocean views, and rooms featuring rainfall showerheads and premium bedding. Many rooms also include a kitchen. Guests consistently praise the super friendly staff, the beautiful and clean pool, and the superb location.

Another highly recommended option is the Hampton Inn Key Largo Manatee Bay, which has an 8.8 rating. This hotel offers a private beach, an outdoor pool with sun loungers, and a poolside bar. Guests can enjoy a free buffet breakfast. Travellers frequently highlight the wonderful and friendly staff, the excellent breakfast, and the comfortable and clean rooms.
What are the best family hotels in Winston Waterways?
For the best family hotels in Winston Waterways, consider the Hampton Inn Key Largo Manatee Bay, Dolphin Point Villas, or Largo Resort.

The Hampton Inn Key Largo Manatee Bay, with an 8.8 rating, is an excellent choice for families. It offers complimentary cribs and sofa beds for extra sleeping arrangements, along with a refreshing pool. Guests can enjoy a free buffet breakfast and complimentary WiFi, and parking is also free. Customers consistently praise the friendly staff, excellent breakfast, and comfortable, clean rooms. It is conveniently located near John Pennekamp Coral Reef State Park, just 2.2 km away.

Another superb option is the 3.5-star Dolphin Point Villas, which boasts an impressive 9.6 rating. This hotel provides free cribs, sofa beds, and connecting rooms, making it ideal for larger families. It features a pool and a private beach on site. Guests frequently comment on the spacious rooms, friendly staff, and the amazing suites. It is situated 2.4 km from John Pennekamp Coral Reef State Park.

The 3-star Largo Resort, rated 9.4, is also highly recommended for families. This resort offers complimentary rollaway beds and cribs, and rooms include a kitchen, which is very convenient for family meals. With a private beach on site, beach views, and ocean views, it provides a wonderful setting. Guests often highlight the super friendly staff, beautiful and clean pool, and clean, amazing rooms. The resort is located 2.5 km from John Pennekamp Coral Reef State Park.
What hotels in Winston Waterways offer free breakfast?
For hotels in Winston Waterways that offer complimentary breakfast, the Hampton Inn Key Largo Manatee Bay is an excellent choice.

The Hampton Inn Key Largo Manatee Bay, with an 8.8 rating, provides a free buffet breakfast daily, which guests consistently describe as excellent. This hotel also offers free WiFi, free self-parking, and complimentary toiletries. Guests frequently praise the friendly staff, comfortable rooms, and overall good service. It is conveniently located near points of interest such as John Pennekamp Coral Reef State Park, just 2.2 km away.
What are the top pet-friendly hotels in Winston Waterways?
For a top pet-friendly hotel in Winston Waterways, the Hampton Inn Key Largo Manatee Bay is an excellent choice.

This hotel, with an 8.8 rating, warmly welcomes both dogs and cats. Guests consistently praise the comfortable and clean rooms, as well as the friendly and wonderful staff. You can also enjoy a free buffet breakfast, complimentary WiFi, and free self-parking. It is conveniently located just 2.2 kilometres from John Pennekamp Coral Reef State Park.
What are the best budget hotels in Winston Waterways?
For budget-friendly accommodation in Winston Waterways, consider the Hampton Inn Key Largo Manatee Bay or the 3-star Largo Resort.

The Hampton Inn Key Largo Manatee Bay has an 8.8 rating and offers a range of complimentary amenities including free WiFi, free self-parking, and a free buffet breakfast, which guests often describe as excellent. Travellers frequently praise the friendly staff and the comfortable, clean rooms. It is conveniently located just 2.2 km from John Pennekamp Coral Reef State Park.

Another excellent option is the 3-star Largo Resort, rated 9.4. This resort provides free WiFi, free self-parking, and complimentary toiletries. Guests appreciate the private beach access, ocean views, and the availability of kitchens in the accommodations. The staff are frequently highlighted as super friendly, and the pool is often described as beautiful and clean. It is also close to John Pennekamp Coral Reef State Park, just 2.5 km away.
What are the most romantic hotels in Winston Waterways for couples?
For a romantic stay in Winston Waterways, couples should consider the Largo Resort.

The 3-star Largo Resort, with an impressive 9.4 rating, is an excellent choice for a romantic getaway. It offers rooms with kitchens, and many feature beach or ocean views, great for a tranquil escape. Guests frequently praise the friendly staff, beautiful and clean pool, and amazing rooms. It is also conveniently located just 2.5 km from John Pennekamp Coral Reef State Park.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winston Waterways hotel for you.
How can I save on a Winston Waterways hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Winston Waterways hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
How much is the nightly rate at a Winston Waterways hotel?
Hotel prices in Winston Waterways often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

Explore a world of travel with Expedia