Winston Waterways Hotels, Key Largo

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
This weekend
26 Sept - 28 Sept
Next weekend
3 Oct - 5 Oct

Filter by

Guest rating
Guest rating
Star rating

2321 Cheap Hotels in Winston Waterways - Specials, Reviews, & Last Minute Deals

Chesapeake Beach Resort
Private beach, white sand, sun-loungers, beach towels

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1537)
"Great location, clean rooms, great amenities and the staff is very friendly. "
The price is AU$291
includes taxes & fees
28 Sept - 29 Sept
Chesapeake Beach Resort
Bayside Inn Key Largo
Terrace/patio

Bayside Inn Key Largo

3.0 star property
8.6 out of 10, Excellent, (1576)
"Great stay "
The price is AU$226
includes taxes & fees
29 Sept - 30 Sept
Bayside Inn Key Largo
Rock Reef Resort
Sun deck

Rock Reef Resort

2.5 star property
9.2 out of 10, Wonderful, (1029)
"Good location. We would stay here again "
Rock Reef Resort
The Pelican Key Largo Cottages
Marina

The Pelican Key Largo Cottages

2.0 star property
8.8 out of 10, Excellent, (1017)
"Great beach and dock area. "
The price is AU$158
includes taxes & fees
6 Oct - 7 Oct
The Pelican Key Largo Cottages
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Private beach, sun-loungers, beach towels, scuba diving

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
8.8 out of 10, Excellent, (85)
"Beautiful place to stay"
The price is AU$419
includes taxes & fees
15 Oct - 16 Oct
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Marina Del Mar Resort and Marina
Exterior

Marina Del Mar Resort and Marina

2.5 star property
8.4 out of 10, Very good, (1609)
"great view from balcony!"
The price is AU$187
includes taxes & fees
27 Oct - 28 Oct
Marina Del Mar Resort and Marina
Coconut Cove Resort and Marina
Exterior

Coconut Cove Resort and Marina

3.0 star property
7.6 out of 10, Good, (818)
"Staff were very nice and welcoming. Nice pool and view. Room was nice clean and comfortable. Definitely would stay again "
The price is AU$199
includes taxes & fees
29 Sept - 30 Sept
Coconut Cove Resort and Marina
Waterside Suites & Marina
Terrace/patio

Waterside Suites & Marina

3.5 star property
8.8 out of 10, Excellent, (1088)
"Excellent hotel "
The price is AU$214
includes taxes & fees
28 Sept - 29 Sept
Waterside Suites & Marina
Seafarer Key Largo
Exterior

Seafarer Key Largo

2.0 star property
9.4 out of 10, Exceptional, (111)
"Rooms are remodeled and staff was great. Would stay here again "
The price is AU$157
includes taxes & fees
28 Sept - 29 Sept
Seafarer Key Largo
Playa Largo Resort & Spa, Autograph Collection
Outdoor pool, pool cabanas (surcharge), pool umbrellas

Playa Largo Resort & Spa, Autograph Collection

4.5 star property
9.0 out of 10, Wonderful, (1001)
"By far one of the best hotels in the keys. "
The price is AU$468
includes taxes & fees
2 Oct - 3 Oct
Playa Largo Resort & Spa, Autograph Collection
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
8.0 out of 10, Very good, (1004)
"Beautiful water and attentive staff."
The price is AU$234
includes taxes & fees
5 Oct - 6 Oct
Fisher Inn Resort & Marina
Hampton Inn Key Largo Manatee Bay
Room, 1 King Bed, Bay View | Beach/ocean view

Hampton Inn Key Largo Manatee Bay

2.5 star property
8.8 out of 10, Excellent, (1028)
"The place was very clean safe and enjoyable. Perfect little paradise."
The price is AU$196
includes taxes & fees
6 Oct - 7 Oct
Hampton Inn Key Largo Manatee Bay
Holiday Inn Key Largo by IHG
2 outdoor pools, pool umbrellas, pool loungers

Holiday Inn Key Largo by IHG

3.0 star property
8.4 out of 10, Very good, (1018)
"Great location for many activities, on site restaurant and tiki bar was perfect."
The price is AU$241
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Key Largo by IHG
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Aerial view

Dove Creek Resort & Marina, Trademark Collection by Wyndham

3.0 star property
7.6 out of 10, Good, (1001)
"Great place to stay!"
The price is AU$192
includes taxes & fees
2 Oct - 3 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Ocean Pointe Suites at Key Largo
BBQ/picnic Area

Ocean Pointe Suites at Key Largo

3.5 star property
8.2 out of 10, Very good, (1014)
"Perfect for a family and adult kids "
The price is AU$219
includes taxes & fees
29 Sept - 30 Sept
Ocean Pointe Suites at Key Largo
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1006)
"Beautiful property and the staff was amazing."
The price is AU$230
includes taxes & fees
30 Sept - 1 Oct
Drop Anchor
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
7.8 out of 10, Good, (1001)
"Loved the rooms very spacious. Ocean view was amazing very close to restaurants "
The price is AU$209
includes taxes & fees
28 Sept - 29 Sept
Hadley Resort and Marina
Amoray Dive Resort
Exterior

Amoray Dive Resort

2.0 star property
9.0 out of 10, Wonderful, (1013)
"Fabulous stay! Location, location! "
The price is AU$169
includes taxes & fees
28 Sept - 29 Sept
Amoray Dive Resort
Reefhouse Resort & Marina
3 restaurants, breakfast, lunch, dinner served; American cuisine

Reefhouse Resort & Marina

3.5 star property
9.2 out of 10, Wonderful, (1308)
"We had a great stay and will definitely stay here again and recommend to others. "
The price is AU$435
includes taxes & fees
5 Oct - 6 Oct
Reefhouse Resort & Marina
Ragged Edge Resort & Marina
Exterior

Ragged Edge Resort & Marina

2.5 star property
9.4 out of 10, Exceptional, (192)
"We enjoyed our stay very much and have already recommended this hotel to friends. Thanks for accommodating our check in and check out. "
Ragged Edge Resort & Marina
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Our guide on where to stay in Winston Waterways

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

Key Largo Village

When in Key Largo Village, you can plan a visit to Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park, some noteworthy sights in the nearby area.

Key Largo Park

Key Largo Park might not have many top sights, but Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park are two attractions nearby that you can check out.

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.

Largo Gardens

Though Largo Gardens may not have many top sights, you can venture to the surrounding area to see attractions like John Pennekamp Coral Reef State Park and MarineLab Undersea Laboratory.

Sexton Cove Estates

When in Sexton Cove Estates, you can plan a visit to Caribbean Club Bar and Key Largo Hammocks State Botanical Site, some noteworthy sights in the nearby area.

Top Winston Waterways Hotel Reviews

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"If you are looking for peace and tranquility, this is where you want to be! This is my go to when I need a getaway."
AIMEE 1-night trip
Posted 22 hours ago
The Pelican Key Largo Cottages

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?

With 18 Expedia hotels and other accommodation options in Winston Waterways to choose from, this is a good starting point for exploring the greater Key Largo area.

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, Lower Sound Point and MarineLab Undersea Laboratory are also worth a stop.

Explore a world of travel with Expedia

Explore a world of travel with Expedia