Winston Waterways Holidays from £934

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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
Price was £1,363, price is now £934 per person
£934
per person
24 Jul - 28 Jul
found 1 day ago
Return direct flight included
London (LHR) to Miami (MIA)
8.6/10 Excellent! (1,388 reviews)
Would stay again - really enjoyed the facility, and the room, and of course the beach. Down side was that in our room, things where worn and dated, maybe this doesn’t matter but I was a little shocked considering the brand reputation.

Reviewed on 17 Jun 2026

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 £16,708, price is now £8,313 per person
£8,313
per person
27 Jul - 2 Aug
found 1 day ago
Return direct flight included
London (LHR) to Miami (MIA)
8/10 Very Good! (1 review)
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

4 out of 5
Price was £1,715, price is now £1,181 per person
£1,181
per person
10 Aug - 17 Aug
found 1 day ago
Return direct flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (205 reviews)
Overall our stay was nice. We loved the shores pool, and paid extra for ocean view and balcony, which was ruined by the sargassum(out of resorts control of course). Also the balcony was not a private balcony attached to our room, it was just an extension off the walk way open to anyone really, so that part is kind of deceiving. Also, not like a huge deal, but we are huge sports fans and we were trying to watch the FiFa and basketball championships game, and there was no cable. Called to try and have it fixed, and they came and fixed it, but there was no directory and there were only 10 channels available, not nba championship game channel. And you had to shuffle through the 100 channels to find random channel that worked. (Again, not a huge deal breaker, but for price, should function) There was also, black mold in the bathroom. I called and alerted front desk twice, they did not seem to care. I had a “vip package” and was supposed to have a late checkout @1pm, and they told me no, that even though that was apart of my package I still was supposed to to call and request it. I did like how close the resort was too a lot of things, and walking distance to good breakfast place frenchies cafe(great coffee)!

Reviewed on 16 Jun 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was £2,439, price is now £1,716 per person
£1,716
per person
10 Aug - 17 Aug
found 1 day ago
Return direct flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (558 reviews)
We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds.

Reviewed on 7 Jun 2026

Amara Cay Resort

Amara Cay Resort

4 out of 5
Matecumbe
Price was £1,630, price is now £1,165 per person
£1,165
per person
10 Aug - 17 Aug
found 1 day ago
Return direct flight included
London (LON) to Miami (MIA)
8.8/10 Excellent! (1,300 reviews)
We had a wonderful stay at Amara Cay and recommend it for an unforgettable vacation. We were treated with great kindness, and the place is beautiful.

Reviewed on 15 Jun 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 £203 per night from 7 Jul to 8 Jul
£203
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (1,764 reviews)
"My girlfriend and I really enjoyed our time at Chesapeake. The room was immaculate and the view from our balcony was amazing. The staff was extremely friendly and helpful. I was able to use fishing gear from the front office to fish the beachfront and harbor in the evenings and they have kayaks available ..."

Reviewed on 17 Jun 2026

Chesapeake Beach Resort
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 £197 per night from 24 Jun to 25 Jun
£197
24 Jun - 25 Jun
includes taxes & fees
9.4/10 Exceptional! (1,491 reviews)
"We had a great time. Walt during check was amazing."

Reviewed on 17 Jun 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
The price is £266 per night from 29 Jun to 30 Jun
£266
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (1,096 reviews)
"Excelente servicio y todo muy limpio"

Reviewed on 16 Jun 2026

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 2,268 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.
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Frequently asked questions

How much does a Winston Waterways travel package cost?
Starting from as little as £934, 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.