Title: Winston Waterways Vacation Packages 2026 from $1,201 | Expedia.com

[Hotels in Winston Waterways](https://expedia.com/Winston-Waterways-Key-Largo-Hotels.0-n553248635976481538-0.Travel-Guide-Filter-Hotels)[Flights to Key Largo](https://expedia.com/Cheap-Flights-To-Key-Largo.d8369.Travel-Guide-Flights)[Things to do in Key Largo](https://expedia.com/Things-To-Do-In-Key-Largo.d8369.Travel-Guide-Activities)[Car Rentals in Winston Waterways](https://expedia.com/Car-Rentals-In-Winston-Waterways.d553248635976481538.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Winston Waterways Vacations from $1,201

## Book a Hotel + Flight or Car together to unlock savings

## Your Winston Waterways Vacation

Planning your next travel adventure just got a lot easier with a vacation package to Winston Waterways. Immerse yourself in the very best this neighborhood has to offer while creating fond memories you'll replay for years. Begin your trip to Winston Waterways by visiting nearby attractions such as [Jimmy Johnsons Big Chill](https://www.expedia.com/Jimmy-Johnsons-Big-Chill-Key-Largo.d553248621563219632.Vacation-Attraction), [John Pennekamp Coral Reef State Park](https://www.expedia.com/John-Pennekamp-Coral-Reef-State-Park-United-States-of-America.d6068611.Vacation-Attraction) and [Caribbean Club Bar](https://www.expedia.com/Caribbean-Club-Bar-Key-Largo.d553248621533115829.Vacation-Attraction). Don't just imagine it — make it happen! Book your perfect Winston Waterways vacation with Expedia and experience travel your way.

## The Latest Winston Waterways Vacation Packages

Price found within the past 48 hours. Click for updated prices.

![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Creekside Inn

Save 100% on your flight

$1,201

per person

Jun 14 - Jun 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (1,027 reviews)

A good place for a short stay. The staff is very friendly. Room was clean and they welcomed our Shih Tzu. It is definitely more of a motel environment and the property is old and undergoing some renovations. If you have loud neighbors, you’ll have to sleep with an extra pillow over your head.

Reviewed on Mar 30, 2026

![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casablanca Miami Beach

North Beach

$1,518

per person

Jun 19 - Jun 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (321 reviews)

Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

![The Club Luxury Condos by Ilios Rentals](https://images.trvl-media.com/lodging/127000000/126250000/126241700/126241626/3d9f5c0d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Club Luxury Condos by Ilios Rentals

Brickell

Save 100% on your flight

$2,778

per person

Jun 19 - Jun 22

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

No reviews

## 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](https://expedia.com/Key-Largo-Winston-Waterways.dx553248635976481538)

![Safety Harbor, Florida](https://images.trvl-media.com/place/553248635975874039/2fee8556-a596-4748-bd3e-bcceb526467b.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Rock Harbor

1 out of top 10 points of interest in this area

 While Rock Harbor isn't home to many top sights, Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill are some notable places to visit nearby. 

[Find hotel + flight trips in Rock Harbor](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Rock%20Harbor&DestID=553248635975874039&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Key West Florida - Sights and Sounds by the water and port](https://images.trvl-media.com/place/553248635976468738/e4cdcb39-8599-4d99-85bd-253ccbd56c96.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Key Largo Village

 While Key Largo Village might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Jimmy Johnson's Big Chill and Jacob's Aquatic Center. 

[Find hotel + flight trips in Key Largo Village](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Key%20Largo%20Village&DestID=553248635976468738&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Silver Shores

 If you're looking for some top things to see and do in Silver Shores and surrounding area, you can visit Bluefin Rock Harbor Marina and Pigeon Key. 

[Find hotel + flight trips in Silver Shores](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Silver%20Shores&DestID=553248635976471567&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Coast of Islamorada, Florida Keys](https://images.trvl-media.com/place/553248635976481780/88fa8714-c73f-4dd9-80be-c5fe469e99a3.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Key Largo Park

 Though Key Largo Park might not have many top sights, you can venture to the surrounding area to see attractions like Jimmy Johnson's Big Chill and Jacob's Aquatic Center. 

[Find hotel + flight trips in Key Largo Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Key%20Largo%20Park&DestID=553248635976481780&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Aerial view, Everglades Natuional Park, FLORIDA, USA, AMERICA](https://images.trvl-media.com/place/553248635976482205/62640ebf-996d-4bf6-9054-b7530b09959b.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sexton Cove Estates

 Though Sexton Cove Estates might not have many top sights, you can venture to the surrounding area to see attractions like Caribbean Club Bar and John Pennekamp Coral Reef State Park. 

[Find hotel + flight trips in Sexton Cove Estates](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sexton%20Cove%20Estates&DestID=553248635976482205&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Winston Waterways Hotel Deals

![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/e9f2dff3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Reefhouse Resort & Marina

103800 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$339 nightly

$376 total

Apr 19 - Apr 20

Total with taxes and fees

9.4/10 Exceptional! (1,398 reviews)

Property is outdated and needs a renovation. Crew in the restaurant is extremely nice but people working in the lobby are not very friendly I wasn’t even feel comfortable with the front desk staff so unprofessional.

Reviewed on Mar 30, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=3427&PinnedHotelID=3427&HadPinnedHotel=true&regionId=553248635976481538)

![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/e2f3e092_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Waterside Suites & Marina

201 Ocean Drive Key Largo FL

Fully refundableReserve now, pay when you stay

$180 nightly

$203 total

Apr 23 - Apr 24

Total with taxes and fees

9/10 Wonderful! (1,270 reviews)

I go every two or three months an have appreciate the deterioration of the rooms, the poor cleaning and the shorting of staff member over the last year. Unfortunately on fridays and saturdays the personal that receive you that represent the face of the place have no experience, and the With a poor ...

Reviewed on Mar 29, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F23%2F2026&endDate=4%2F24%2F2026&selected=13719&PinnedHotelID=13719&HadPinnedHotel=true&regionId=553248635976481538)

![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL

Fully refundableReserve now, pay when you stay

$385 nightly

$433 total

Apr 13 - Apr 14

Total with taxes and fees

8.6/10 Excellent! (1,021 reviews)

Very good.

Reviewed on Mar 30, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F13%2F2026&endDate=4%2F14%2F2026&selected=14042&PinnedHotelID=14042&HadPinnedHotel=true&regionId=553248635976481538)

[See all 2,289 properties in Winston Waterways](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&regionId=553248635976481538)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

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Kid Friendly Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

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![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ Friendly Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adventure Vacations

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Where to go when

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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Honeymoon Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Mountain Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Fishing Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Adults Only Vacations

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Scuba Diving Vacations

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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Yoga Vacations

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Solo Vacations

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.