Winston Waterways Holidays

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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
Price was €1,883, price is now €967 per person
€967
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Very cool vintage style hotel. Rooms were comfortable and clean! Hotel restaurant had great options and great food! The bar has good drinks and is very conveniently located. Great location to great food, bars and beach. I would stay here again for sure!

Reviewed on 13 Jan 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 €27,167, price is now €12,729 per person
€12,729
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was €2,834, price is now €1,500 per person
€1,500
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Average hotel. Noticed few things during our stay. - The staff outside the hotel is "valet only" staff. Don't expect anyone to help you with your bags. - One day, our room was not made up. Looks like they are "scheduled". Not sure if they do it daily by default. - Zero sound-proof. We heard literally everything our room neighbors said. - We didn't rent a car but if you do, expect a front parking of just 4-5 cars. So, don't take a car with you. - No late checkout available. Good things. - The pool is good.

Reviewed on 12 Jan 2026

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Price was €1,826, price is now €1,026 per person
€1,026
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,935 reviews)
다 좋았어요. 그런데 엘레베이터가 한대가 고장나서 층을 이동할때 느렸습니다.

Reviewed on 13 Jan 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was €1,789, price is now €1,014 per person
€1,014
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
First time in Miami and the President was nice, right in the middle of the action of South Beach! Dont expect this to a quiet quaint type hotel or location, lots of hustle and bustle! I liked it because was so close to the ocean and ocean drive and all the shops and restuarants. You dont need to rent a car if your gonna stay on south beach the entire time. Parking garage 2 blocks down 10 min walk is $20 a day

Reviewed on 13 Jan 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
Baker's Cay is a gem within Key Largo. It has an incredible beach where are you likely to spot wildlife like manatees, dolphins, and sharks right from the beach or their own private pier. #LifeAtExpediaGroup

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 €231 per night from 28 Jan to 29 Jan
€231
28 Jan - 29 Jan
includes taxes & fees
9.2/10 Wonderful! (1,621 reviews)
The hotel is in a perfect location, and offers so much on premise

Reviewed on 7 Jan 2026

Chesapeake Beach Resort
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

2.5 out of 5
527 Caribbean Drive Key Largo FL
Fully refundableReserve now, pay when you stay
The price is €138 per night from 20 Jan to 21 Jan
€138
20 Jan - 21 Jan
includes taxes & fees
8.4/10 Very Good! (1,673 reviews)
Amazing

Reviewed on 7 Jan 2026

Marina Del Mar Resort and Marina
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 €170 per night from 21 Jan to 22 Jan
€170
21 Jan - 22 Jan
includes taxes & fees
8.8/10 Excellent! (1,185 reviews)
We just needed a short stay this time, but everything was wonderful.

Reviewed on 9 Jan 2026

Waterside Suites & Marina
See all 2,299 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.

Frequently asked questions

How much does a Winston Waterways holiday package cost?
Our Winston Waterways holiday packages, which start at just €967, are the perfect way to save precious money. Choose your preferred flights, hotels and rental cars to create a personalized escape.
How do I get a cheap travel package to Winston Waterways?
If you love scoring a bargain, bundle your bookings into a Winston Waterways holiday package. Whether you need hotels, flights, tours or rental cars, you can browse and book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has over 550 air carriers and 1,000,000 hotel options all over the world to pick from. Fly with who you prefer, stay where you like and save your hard-earned money — now that's the perfect escape!
Where should I stay in Winston Waterways?
With loads to discover in Winston Waterways, it'd be convenient for you to lock in a hotel close to its attractions. Jimmy Johnsons Big Chill, Caribbean Club Bar and MarineLab Undersea Laboratory are some fascinating ones to put on your to-do list.
How far in advance should I book my Winston Waterways holiday?
Search Expedia to compare international flights as soon as possible. You can normally purchase a ticket up to a year in advance. If it's too early for your preferred carrier, or you've left things to the last minute, don't despair. Cheap tickets to Winston Waterways sometimes emerge just weeks before the date of departure.
What does an Expedia Winston Waterways travel package include?
Select from any combination of flights, rental cars and hotels. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's possible too. The choice is yours when it comes to arranging your dream Winston Waterways getaway.
What should I know before booking a Winston Waterways travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and score fantastic discounts. Hotels aren't your only choice, though. Book with us and take your pick of island resorts, cabins in the mountains and even ranches and treehouses!
Can I choose my airline with a Winston Waterways Expedia holiday package?
Most definitely. Expedia has access to more than 550 airlines all over the world, so you can customize your Winston Waterways holiday according to your travel needs.
If I'm not able to travel, can I cancel my Winston Waterways holiday package?
You can. We realise life happens, so we're happy to help if you need to make changes to your Winston Waterways holiday package. It may be possible to cancel or change your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.