Key Haven Kid friendly Vacations

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Flight and Kid friendly hotel deals in Key Haven

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

The Perry Hotel & Marina Key West

CA $1,274

per person

Sep 26 - Oct 3

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Matt's Stock Island restaurant that is on the property is one of our go-to stops for brunch. The hotel room was great and we love that the property is dog friendly with a dog park.

Reviewed on Aug 16, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,295

per person

Nov 3 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!

Reviewed on Aug 16, 2026

Parrot Key Hotel & Villas

Northside Resort

CA $1,602

per person

Nov 3 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,438 reviews)

Recomendado 100%, hotel agradable, bonito y en buena localidad. Las habitaciones limpias y el personal atento.

Reviewed on Aug 17, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,247

per person

Nov 3 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Great location , able to walk to restaurants on Duval Street . Nice pools , good services

Reviewed on Aug 16, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,877

per person

Sep 26 - Oct 3

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,002 reviews)

Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees.

Reviewed on Aug 14, 2026

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5* Kid friendly holidays in Key Haven

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

The Porch on Frances Inn

Old Town Key West

CA $1,609

per person

Nov 9 - Nov 13

just found

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (137 reviews)

Great value

Reviewed on Aug 13, 2026

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3 Night Kid friendly holidays in Key Haven

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

The Perry Hotel & Marina Key West

CA $1,177

per person

Oct 9 - Oct 12

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Matt's Stock Island restaurant that is on the property is one of our go-to stops for brunch. The hotel room was great and we love that the property is dog friendly with a dog park.

Reviewed on Aug 16, 2026

Pier House Resort & Spa

Key West Historic District

CA $1,625

per person

Sep 21 - Sep 24

just found

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,258 reviews)

This was a convenient, perfect hotel for a last-minute getaway to Key West. It sits at the end of Duval St, right on the beach. We had access to swim in their private small beach area or pool. They had a fun pub room, tiki bar, and restaurant on the premises. We enjoyed the sunset and sunrise views, and we could walk to shopping, museums, restaurants, and bars. The room was fresh and clean, with comfortable beds.

Reviewed on Aug 17, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,829

per person

Nov 5 - Nov 8

found 10 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Great location , able to walk to restaurants on Duval Street . Nice pools , good services

Reviewed on Aug 16, 2026

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4 Night Kid friendly holidays in Key Haven

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

Coconut Beach Resort

Old Town Key West

CA $1,758

per person

Sep 17 - Sep 21

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.8/10 Excellent! (212 reviews)

The property was advertised to have a private white sand beach which is why I made the reservation. It was covered feet deep in seaweed. Granted there are things out of the property's control, but there should have been a warning on their website that the beach may not be available for use. Also, we were given two small individual size packets of coffee for a twelve cup coffee maker for four days. I went and bought a bag of coffee but then realized there were no other filters either. I enjoy waking up early, and reading outside. The last morning, the staff was out landscaping and hosing off the patio and lounge chairs next to me. I got overspray blown in my face.

Reviewed on Aug 14, 2026

The Key West Hotel

Key West Historic District

CA $3,533

per person

Nov 3 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (561 reviews)

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Ridley House - Key West Historic Inns

Key West Historic District

CA $2,109

per person

Nov 3 - Nov 7

found 19 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (946 reviews)

This is a must stay property! It is walking distance to everything. Your very cold room with the softest mattress ever is always 7 minutes away or less.

Reviewed on Aug 13, 2026

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What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Key Haven are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Key Haven.

Are there cheap family vacations to Key Haven?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in Key Haven depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

Can I book an all-inclusive family vacation in Key Haven?

Yes, you'll find plenty of all-inclusive family vacation packages for Key Haven. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in Key Haven, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Key Haven or something a bit more relaxed.

Can I find luxury family vacations in Key Haven?

If you're looking for a luxury family vacation to Key Haven, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Key Haven.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Key Haven are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.