Title: Windley Key Kid friendly Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windley Key Kid friendly Vacations

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

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Kid friendly vacation packages in Windley Key

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

![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Solé Miami, A Noble House Resort

Ocean Four

Save 100% on your flight

$644

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,935 reviews)

It’s hard to believe this is a 4 star hotel. The rooms are small and dated. We found some insect in our bathroom. They have only 1 or 2 working elevators at anytime and you need to wait for sometime. There was a lack of amenities that I thought would be complementary. For example I left my tooth brush and had to buy one in the store instead. Small things but at the price point it doesn’t quite add up. Dining was good, this was a highlight, several great waitstaff including Daniel. The beach access is incredible, they set up your chairs a towels and you can order drinks. Housekeeping, waitstaff and beach staff were amazing.

Reviewed on Mar 4, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,123

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/0ba3314b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pelican Hotel

South Beach

Save 100% on your flight

$898

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (432 reviews)

The hotel was OK but pricey. Breakfast included but limited to three dishes. The access to the beach waa 2 blocks away. No coffee. The staff was very good. maker in the room. The hotel carpets were overused

Reviewed on Mar 3, 2026

![Mondrian South Beach](https://images.trvl-media.com/lodging/3000000/2200000/2190300/2190271/ac45c0a6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Mondrian South Beach

South Beach

Save 100% on your flight

$730

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (2,697 reviews)

The staff 5 stars the bartender outside at the restaurant he was always smiling it was so busy and he was never rude always great attitude super amazing

Reviewed on Mar 3, 2026

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

Save 100% on your flight

$3,321

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,451 reviews)

Good experience, pricey amenities

Reviewed on Mar 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Kid friendly vacations in Windley Key

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

![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Cheeca Lodge & Spa

Matecumbe

Save 100% on your flight

$1,128

per person

May 24 - May 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,298 reviews)

Yes clean and nice staff

Reviewed on Feb 21, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,123

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

Save 100% on your flight

$3,321

per person

May 9 - May 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,451 reviews)

Good experience, pricey amenities

Reviewed on Mar 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Kid friendly vacations in Windley Key

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

![Isla Bella Beach Resort & Spa](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/f6566b0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Isla Bella Beach Resort & Spa

Save 100% on your flight

$874

per person

Apr 14 - Apr 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,096 reviews)

Beautiful sunrises and sunsets from oceanfront room.

Reviewed on Mar 4, 2026

![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,020

per person

May 14 - May 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/5c0d327a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### 1 Hotel South Beach

South Beach

Save 100% on your flight

$1,233

per person

Apr 19 - Apr 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

9.4/10 Exceptional! (1,451 reviews)

Good experience, pricey amenities

Reviewed on Mar 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Kid friendly vacations in Windley Key

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

![President Hotel Villa](https://images.trvl-media.com/lodging/11000000/10620000/10612900/10612810/5a873fda_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### President Hotel Villa

South Beach

Save 100% on your flight

$698

per person

Apr 10 - Apr 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,007 reviews)

Mike and Henry were extremely helpful with directions, valet service assistance, and any questions were answers, making it a very pleasant experience!

Reviewed on Mar 3, 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

$2,028

per person

May 18 - May 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

5.8/10 (320 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

![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

$709

per person

May 21 - May 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

7.8/10 Good! (1,007 reviews)

Room did not have a water view as was listed on the site, pool was cold but clean. Staff was friendly and helpful.

Reviewed on Mar 4, 2026

Don't see what you're looking for?

See all available trips from Columbus to Windley Key

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## FAQs: family vacation packages in Windley Key

####  How can I find the best family vacation packages in Windley Key? 

 For fam-tastic vacation packages in Windley Key, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play. 

####  How can I book family-friendly vacations in Windley Key on a budget? 

 For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant. 

####  What does a family trip to Windley Key cost? 

 You could book your amazing family trip to Windley Key just $644\. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply. 

####  Can I book an all-inclusive Windley Key family vacation package? 

 Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore. 

####  How can I plan a fun family vacation in Windley Key? 

 Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes. 

####  How can I find Windley Key family vacation deals? 

 Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Windley Key landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains. 

####  Can I book a Windley Key family vacation package with free cancellation and/or flexible dates? 

 Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options. 

####  Why should I book my Windley Key family trip with Expedia? 

 You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more. 

## More vacations you might like

![](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

[](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Kid Friendly Vacations

[](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

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

Romantic Vacations

[](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

![LGBTQ+ Vacation Packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/01/23/352703_320x320_32517_Miami_LGBTQ.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ+ Vacations

[](https://expedia.com/lp/theme-vacations/gay-friendly-vacations?rfrr=editorial.LGBTQ+_Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click)

![Where to go when](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://www.expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to go when.click)

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

Honeymoon Vacations

[](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click)

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

Mountain Vacations

[](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click)

![](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

[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click)

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

Waterpark Vacations

[](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click)

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

Scuba Diving Vacations

[](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click)

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

Yoga Vacations

[](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Cheap Vacations

[](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Solo Vacations

[](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click)

### Top Kid friendly Vacation Destinations

> - [Kid Friendly Vacations in Florida ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/211/Florida)
> - [Kid Friendly Vacations in California ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/206/California)
> - [Kid Friendly Vacations in Cancun ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/179995/Cancun)
> - [Kid Friendly Vacations in Costa Rica ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/42/Costa-Rica)
> - [Kid Friendly Vacations in the USA ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/201/United-States-Of-America)
> - [Kid Friendly Vacations in Las Vegas ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/178276/Las-Vegas)
> - [Kid Friendly Vacations in New York ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/178293/New-York)
> - [Kid Friendly Vacations at the Grand Canyon ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/6140738/Grand-Canyon)
> - [Kid Friendly Vacations in Texas ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/245/Texas)
> - [Kid Friendly Vacations in Colorado ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/207/Colorado)
> - [Kid Friendly Vacations in Gatlinburg ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/7474/Gatlinburg)
> - [Kid Friendly Vacations in Myrtle Beach ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/601685/Myrtle-Beach)
> - [Kid Friendly Vacations in Jamaica ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/88/Jamaica)
> - [Kid Friendly Vacations in Hawaii ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/213/Hawaii)
> - [Kid Friendly Vacations in Chicago ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/178248/Chicago)
> - [Kid Friendly Vacations in Tennessee ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/244/Tennessee)
> - [Kid Friendly Vacations in Miami Beach ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/8833/Miami-Beach)
> - [Kid Friendly Vacations in Washington ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/249/Washington)
> - [Kid Friendly Vacations in the Caribbean ](https://www.expedia.com/lp/theme-vacations/kid-friendly-vacations/6022969/Caribbean)

## More Vacation Ideas

[Flights to Windley Key

](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[

Windley Key Hotels

](https://expedia.com/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[

Vacation Rentals in Windley Key

](https://expedia.com/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[

Car Rentals in Windley Key

](https://expedia.com/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[

Windley Key Vacations

](https://expedia.com/Windley-Key.d553248635976197663.Destination-Travel-Guides)[

Things to do in Windley Key

](https://expedia.com/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)

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

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app