Winston Waterways Holidays from £1,319

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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.
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Save 100% on your flight
Price was £2,031, price is now £1,319 per person
£1,319
per person
2 Oct - 9 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Miami (MIA)
8.6/10 Excellent! (1,439 reviews)
Ambience

Reviewed on 1 Aug 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was £11,490, price is now £4,363 per person
£4,363
per person
18 Oct - 24 Oct
found 1 day ago
Return direct flight included
London (LHR) to Miami (MIA)
5.8/10 (326 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.

Reviewed on 23 Jul 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was £4,454, price is now £2,581 per person
£2,581
per person
2 Oct - 9 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Miami (MIA)
9.4/10 Exceptional! (1,571 reviews)
Great place

Reviewed on 31 Jul 2026

EAST Miami Residences

EAST Miami Residences

5 out of 5
Brickell
Save 100% on your flight
Price was £2,626, price is now £1,649 per person
£1,649
per person
24 Oct - 30 Oct
found 14 hours ago
Return direct flight included
Glasgow (GLA) to Miami (MIA)
9.2/10 Wonderful! (139 reviews)
Ji

Reviewed on 1 Aug 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was £3,135, price is now £1,993 per person
£1,993
per person
3 Oct - 10 Oct
found 18 hours ago
Return direct flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on 27 Jul 2026

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
A wooden pier extending into calm waters, with a covered area at the end.

Rock Harbor

1 out of top 10 points of interest in this area

While there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.

Find hotels in Rock Harbor

Top hotels in Winston Waterways

Reefhouse Resort & Marina

Reefhouse Resort & Marina

4.5 out of 5
103800 Overseas Hwy Key Largo FL
Fully refundableReserve now, pay when you stay
The price is £212 per night from 9 Aug to 10 Aug
£212
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (1,493 reviews)
"Great view and pool area."

Reviewed on 1 Aug 2026

Reefhouse Resort & Marina
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 £259 per night from 27 Aug to 28 Aug
£259
27 Aug - 28 Aug
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Waterside Suites & Marina

Waterside Suites & Marina

3.5 out of 5
201 Ocean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is £115 per night from 16 Aug to 17 Aug
£115
16 Aug - 17 Aug
includes taxes & fees
Waterside Suites & Marina
See all 2,269 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 £1,319, 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.

Things to do

Key Largo Coral Reef Glass Bottom Boat Adventure

Key Largo Coral Reef Glass Bottom Boat Adventure

£34
per adult
96% of travellers recommend
Key Largo Coral Reef Glass Bottom Boat Adventure
Florida Keys Audio Guided Tour

Discover Florida Keys: A Self-Guided Tour

£6
per adult
Discover Florida Keys: A Self-Guided Tour
Snorkel Tours to Florida Keys National Marine Sanctuary also know as John Pennekamp Underwater State Park in Key Largo.

Snorkel Tours to Shallow Coral Reefs at Pennekamp Underwater Park

£57
per adult
Snorkel Tours to Shallow Coral Reefs at Pennekamp Underwater Park
See all activities in Key Largo

* 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.