Winston Waterways Holidays from £599

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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.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was £1,040, price is now £599 per person
£599
per person
22 Sept - 28 Sept
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.

Reviewed on 16 Aug 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
Price was £15,480, price is now £7,030 per person
£7,030
per person
22 Sept - 28 Sept
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was £4,323, price is now £2,338 per person
£2,338
per person
27 Oct - 3 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,265 reviews)
Incredible service and friendly staff. Will definitely be back!

Reviewed on 21 Aug 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was £2,171, price is now £1,192 per person
£1,192
per person
25 Oct - 1 Nov
found 12 hours ago
Return direct flight included
London (LON) to Miami (MIA)
8.8/10 Excellent! (1,193 reviews)
I stayed there for two nights, but the housekeeping never came, when I checked with the reception at 4 PM about housekeeping, they said because the hotel is 95% full, and the housekeeping cannot clean every room. (housekeeping close at 4:30 PM) So I asked for two clean towels, it didn’t arrive until two hours later. They charge an extra $52 resort fee for each night, that should include two bottle of water each night. But when I try to get it a second day, they said water it’s only given out on the first day. Aside from their service, and poor cleaning condition, the beach is nice

Reviewed on 21 Aug 2025

President Villa

President Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was £1,273, price is now £763 per person
£763
per person
7 Nov - 14 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Hospitable staff, clean, location ideal to walking distance to beach and shopping. Safe place!

Reviewed on 8 Aug 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 John Pennekamp Coral Reef State Park, 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 £138 per night from 21 Sept to 22 Sept
£138
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,501 reviews)
"Excellent location on the ocean and everything was really perfect. will stay there again"

Reviewed on 17 Aug 2025

Chesapeake Beach Resort
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

3 out of 5
99701 Overseas Hwy, Key Largo, FL
Fully refundable
The price is £119 per night from 7 Sept to 8 Sept
£119
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Staff was very pleasant and when asked for anything they were right back with the items in no time."

Reviewed on 18 Aug 2025

Holiday Inn Key Largo by IHG
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
Fully refundableReserve now, pay when you stay
The price is £253 per night from 3 Sept to 4 Sept
£253
3 Sept - 4 Sept
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Excellent would visits again"

Reviewed on 17 Aug 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,262 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 £599, 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.