Winston Waterways Holidays from £641

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Your Winston Waterways Holiday

Book a Winston Waterways holiday package and experience the atmosphere and rhythm of this captivating neighbourhood. With all your travel plans worked out, the only thing you need to concentrate on here is having a good time. Hoping to explore the sights during your trip to Winston Waterways? Be sure to stop by nearby attractions such as John Pennekamp Coral Reef State Park, Jimmy Johnsons Big Chill and Caribbean Club Bar. Stop daydreaming and start doing. When it's time to book your holiday to Winston Waterways, Expedia will help you get there.

Price found within the past 48 hours. Click for updated prices.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LGW) to Miami (MIA)
9/10 Wonderful! (125 reviews)
Great place and good value. Only complain, they should put black out at the bedroom! To bright in the morning.

Reviewed on 19 Jun 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
per person
15 Sept - 21 Sept
found 1 day ago
Return direct flight included
London (LGW) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on 31 May 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
2 Aug - 9 Aug
found 12 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
8/10 Very Good! (1 review)
iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LGW) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Very relaxing, & private. Loved it! Very easy to get ahold of management for any needs.

Reviewed on 22 Jun 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LGW) to Miami (MIA)
9/10 Wonderful! (63 reviews)
No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on 23 May 2025

Where to stay in Winston Waterways

Find the best Winston Waterways areas and neighborhoods for the activities you enjoy most. Learn more about Winston Waterways
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Key Largo Village

When in Key Largo Village, you can plan a visit to Jimmy Johnson's Big Chill and Jacob's Aquatic Center, some noteworthy sights in the nearby area.

Find hotels in Key Largo Village

Top hotels in Winston Waterways

Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is £168 per night from 7 Jul to 8 Jul
£168
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (1,479 reviews)
"Nice day , check in super fast , room ready in early time , clean pools and a beautiful beach access . The only problem was my AC , it wasn’t cooling enough in the night. But all the other Amenities and services was great."

Reviewed on 30 Jun 2025

Chesapeake Beach Resort
Hampton Inn Key Largo Manatee Bay
Hampton Inn Key Largo Manatee Bay
2.5 out of 5
102400 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is £112 per night from 16 Jul to 17 Jul
£112
16 Jul - 17 Jul
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Ok for a short stay."

Reviewed on 28 Jun 2025

Hampton Inn Key Largo Manatee Bay
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Baker's Cay Resort Key Largo, Curio Collection by Hilton
4 out of 5
97000 Overseas Hwy, Key Largo, FL
The price is £284 per night from 10 Jul to 11 Jul
£284
10 Jul - 11 Jul
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Amazing place!!! People Rooms Beach Everything!!!! In love with this place !!!"

Reviewed on 27 Jun 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,249 properties in Winston Waterways
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Winston Waterways travel package cost?
Starting from as little as £641, you can build your own Winston Waterways package the way you want. Simply combine flights, hotels and car rentals and be rewarded with discounts.
If I'm not able to travel, can I cancel my Winston Waterways travel package?
You can cancel your Winston Waterways booking if your plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Winston Waterways?
Our Winston Waterways travel packages offer plenty of savings for the savvy wanderer. For the best deal, simply combine your flights, hotels and extras (including tours) into an affordable package. But great bargains are only the start of your next big adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 properties around the world to pick from. Whatever your style, there's a package with your name on it.
Does Expedia offer Book Now, Pay Later Winston Waterways holidays?
Expedia has joined forces with online lender Klarna to make booking your next getaway easier on your wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you see an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Winston Waterways?
With so much to explore in Winston Waterways, it's a good idea to secure a room in a hotel near its attractions. Jimmy Johnsons Big Chill, Caribbean Club Bar and Jacobs Aquatic Centre are some interesting ones to add to your must-see list.
What are the top hotels in Winston Waterways?
Book a stay at Bayside Inn Key Largo. It's one of this area's most in-demand hotels. Another highly rated option in Winston Waterways is Holiday Inn Key Largo, an IHG Hotel.
How far in advance should I book my Winston Waterways holiday?
While prices change from time to time, we generally advise booking your seats as early as possible. Most international airfares are found on Expedia up to a year in advance. If you're booking late, you might still be in luck. Cheap tickets to Winston Waterways sometimes emerge just weeks before departure.
What does an Expedia Winston Waterways travel package include?
Packages include rental cars, flights and hotels, but you can combine any of them to create your ideal Winston Waterways getaway. You can also add on some tours and activities once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Winston Waterways travel package?
An Expedia travel package can be tailored to your budget and is a fantastic way to make your money go further. How much you include is completely up to you. Rental cars, hotels and flights --- come up with a combination that suits your plans.
Can I choose my airline with a Winston Waterways Expedia travel package?
Most definitely. Expedia has more than 550 airline partners to select from around the world. With so many choices, finding the perfect carrier to fly you to Winston Waterways won't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.