Winston Waterways Holidays from £1,058

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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.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was £1,751, price is now £1,058 per person
£1,058
per person
16 Jul - 23 Jul
found 1 day ago
Return direct flight included
London (LON) to Miami (MIA)
8.2/10 Very Good! (1,001 reviews)
Great service, very clean hotel.

Reviewed on 29 Apr 2026

Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was £5,165, price is now £2,155 per person
£2,155
per person
21 Jun - 28 Jun
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Miami (MIA)
8.2/10 Very Good! (151 reviews)
The room was overall good order and clean. 5 Star is reserved for properties that go above and beyond with details and exceed expectations. This property was great with regards to cleanliness, but not 5 star. Minor details, small spots here and there and other fine details that can be overlooked but keeps it from a 5 star rating

Reviewed on 1 May 2026

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was £2,075, price is now £1,163 per person
£1,163
per person
16 Jul - 23 Jul
found 1 day ago
Return direct flight included
London (LON) to Miami (MIA)
8.6/10 Excellent! (1,003 reviews)
I spent 3 days and was amazing, the location was incredible, the room beautiful, air conditioned and elevator worked and was good, the only problem is that they gibe you chairs for the beach and then they force you to pay for umbrella, I would rather dont have anything but the sneaky way the umbrella people worked was not good. But to be honest I would go back to that hotel many many more times, it was as beautiful as it was on the pictures and more.

Reviewed on 29 Apr 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was £3,253, price is now £1,919 per person
£1,919
per person
21 Jun - 28 Jun
found 1 day ago
Return direct flight included
Aberdeen (ABZ) to Miami (MIA)
8/10 Very Good! (1,141 reviews)
Nice Hotel near south beach outside space and public areas are beautiful, the room was ok could do with being modernised

Reviewed on 1 May 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was £3,264, price is now £1,990 per person
£1,990
per person
22 Jun - 29 Jun
found 1 day ago
Return flight included
Aberdeen (ABZ) to Miami (MIA)
9.2/10 Wonderful! (452 reviews)
Pros: Clean rooms, nice staff, close to the beach. Cons: resort fees per day, and hearing the noise outside my room (inside the hotel from staff or other guests). Overall, it was a nice and peaceful experience.

Reviewed on 29 Apr 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
Safety Harbor, Florida

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

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 £189 per night from 4 May to 5 May
£189
4 May - 5 May
includes taxes & fees
Chesapeake Beach Resort
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 £300 per night from 2 Jun to 3 Jun
£300
2 Jun - 3 Jun
includes taxes & fees
8.6/10 Excellent! (1,056 reviews)
The name of this place should be Baker’s Cay FAMILY resort. While I totally understand this was not an adults only property, there were screaming kids everywhere. The biggest issue is no soundproofing in the rooms. We were woken in the middle of the night every night and early mornings by a crying ...

Reviewed on 30 Apr 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 £260 per night from 26 May to 27 May
£260
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (1,410 reviews)
The Reef house is a beautiful place to stay. Good view, not crowded, super nice, friendly, helpful staff! the only negative thing was there was no microwave in the room. Highly recommend staying here!!!

Reviewed on 1 May 2026

Reefhouse Resort & Marina
See all 2,311 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
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Family Friendly Holidays

Frequently asked questions

How much does a Winston Waterways travel package cost?
Starting from as little as £1,058, 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.