Raccoon Key Kid friendly Vacations

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Top Kid friendly vacation packages in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,329
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Liked the bungalow, smaller but functional. The only problem I had was the air conditioning couldn’t cool the room efficiently and had to keep emptying the dehumidifier. Love the location, pool and hotel.

Reviewed on Oct 17, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
Save 100% on your flight
$1,463
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
.

Reviewed on Oct 17, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$2,319
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,721
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
I do not have enough adjectives to describe how wonderful The Gardens Hotel is. From the moment we entered the gate, we knew this place was special. The staff was incredible, the accommodations were elegant, the grounds were phenomenal, the pool, bar, live nightly music, breakfast, wine bar, location- all top notch. The attention to every single detail was intentionally thought out. We walked everywhere we wanted to go from this central location. Make sure you take the time to relax and enjoy the pool and other amenities. We are spoiled for life by this hotel!!

Reviewed on Oct 17, 2026

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

Key West Historic District
Save 100% on your flight
$1,561
per person
Jan 8 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (486 reviews)
Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha.

Reviewed on Oct 16, 2026

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3 Night Kid friendly vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$1,224
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
.

Reviewed on Oct 17, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,721
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
I do not have enough adjectives to describe how wonderful The Gardens Hotel is. From the moment we entered the gate, we knew this place was special. The staff was incredible, the accommodations were elegant, the grounds were phenomenal, the pool, bar, live nightly music, breakfast, wine bar, location- all top notch. The attention to every single detail was intentionally thought out. We walked everywhere we wanted to go from this central location. Make sure you take the time to relax and enjoy the pool and other amenities. We are spoiled for life by this hotel!!

Reviewed on Oct 17, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$1,324
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
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4 Night Kid friendly vacations in Raccoon Key

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

The Gardens Hotel

Old Town Key West
$1,998
per person
Jan 10 - Jan 14
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
I do not have enough adjectives to describe how wonderful The Gardens Hotel is. From the moment we entered the gate, we knew this place was special. The staff was incredible, the accommodations were elegant, the grounds were phenomenal, the pool, bar, live nightly music, breakfast, wine bar, location- all top notch. The attention to every single detail was intentionally thought out. We walked everywhere we wanted to go from this central location. Make sure you take the time to relax and enjoy the pool and other amenities. We are spoiled for life by this hotel!!

Reviewed on Oct 17, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,665
per person
Dec 27 - Dec 31
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (563 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$2,319
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,024 reviews)
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FAQs: family vacation packages in Raccoon Key

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

For fam-tastic vacation packages in Raccoon 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 Raccoon 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 Raccoon Key cost?

You could book your amazing family trip to Raccoon Key just $1,224. 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 Raccoon 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 Raccoon 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 Raccoon 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 Raccoon 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 Raccoon 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 Raccoon 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.

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

$79
per adult
98% of travellers recommend
Sunset Sail in Key West with Beverages Included
See all activities in Raccoon Key

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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.