Beach vacation advice

November 13, 2018 7:58 PM

Beach vacation in January wanted. I want to go to the beach in early January with my family- two adults, three kids (6, 4, 1 year old). I have a particular vision and I need advice on where to find it and whether my idea is actually going to be relaxing.

I've been working like crazy since April and I need a break. I want to take my kids to the beach for some rest and relaxation. My requirements: housing in the beach, walk out the door and be on sand in a location where we can hang out on the beach. A fairly easy trip from Milwaukee WI. This means no more than one connection and ideally overall travel time of under 6 hours. Desires: USA, kids don't have passports yet (willing to get them if the location meets the rest of my desires); house/cottage with kitchen and at least two bedrooms, 3 ideally. Not completely touristy it at least not just all inclusive resorts.

I have been casually browsing flights and Airbnb on Caribbean islands. Nothing has really jumped out at me as so good that I'm inspired to book it. Key West seems appealing but also maybe not beachy enough? I'm not looking for luxury, but I'm willing to spend money for the right trip. I'm thinking if I don't book this soon then it won't happen.

I'm hoping to send 5-7 days reconnecting with my family, playing on the beach, in the water, checking out low key casual tourist attractions. Eating out some but also hoping for the ability to do some easy meals in the hotel/ rental. Should I be more focused on resort options?

Do you have a recommendation of particular place to stay? Recommendation on a location to focus on? Other advice or reality checks?

posted by sulaine to Travel & Transportation (12 answers total)

We rented a beach house one summer that was similar to what you described but we got it because we noticed a little “for rent in August” sign scribbled on an envelope in the window when we went by on a drive at Christmas. I think those houses are usually lived in, often by older people, and not necessarily on air B and B and they rent to the same people every year. I would keep up the detective work to find a house like this for future years but I think a condo on a resort sounds nice!
posted by catspajammies at 8:34 PM on November 13, 2018

Key West isn't what you're looking for - not only not enough beach, but really no houses like you're envisioning, and not "relaxing" in the same way. But one of the other keys might work.
posted by Miko at 8:38 PM on November 13, 2018 [1 favorite]

Ive been to the big island in Hawaii in February and the weather is great but might be too far? There are some direct flights from Chicago, not sure about Milwaukee. We stayed at a family friendly resort with pools, etc, and beaches nearby, snorkeling, pretty relaxing. There are places right on the beach too. It is U.S. but a long flight.
posted by j810c at 8:57 PM on November 13, 2018

When my Ying Yangs were 4, 5,and 6 we rented a house in Jamaica with another couple that came with a pool, a staff including cook and maid, a car and driver (may have been an add on) and access to the beach at Tryall.

We ordered food in advance and any meal we wanted prepared for us was. We went out 2x. The property's caretaker also had a garden in the back. He grew veggies which were delicious and also cover for the Jamaican bud he cultivated. Also delicious.

Great vacation that even my kids remember. Reasonable cost too. Easy flight from O'Hare. At the time, I don't think my kids even needed a passport to get in to Jamaica or back into the states. That likely has changed. (I think you should get passports for your children even if you do not need them now. If you ever NEED TO LEAVE, you can grab the kids, spouse and passports and go.

I think you can get the vacation you want if you look for rental houses in Jamaica or one of the Caribbean Islands. I will see if I can find the rental company information. If I find it, I will memail you.
posted by AugustWest at 10:11 PM on November 13, 2018

I think you can get what you're looking for closer to home and with less cost in the Florida Panhandle. Something like this maybe? Swimming in the Gulf in January probably no but there's a pool and the beach and it would be fun for the kids.

Otherwise I would go to Hawaii.
posted by DarlingBri at 1:16 AM on November 14, 2018

I went to Sanibel last winter, and it was what you're describing. Seems like 90% of the island is vacation rentals.
posted by kevinbelt at 4:37 AM on November 14, 2018

Check out hotels around San Juan PR. Easy to get to from the midwest and really wonderful. My friends have gone every year with their young children because it's such a good place to take kids. I have stayed at the Embassy Suites there but it's a couple of blocks from the beach; you can do better than that. But yeah, consider a hotel. When staying at people's houses near the beach I've had to do a lot of cleaning every day.
posted by BibiRose at 5:46 AM on November 14, 2018 [1 favorite]

I'm going to line up behind snickerdoodle and AugustWest and say that with little kids you don't want a little AirBnB. What you want is an oceanfront all-inclusive. Damn hard to find in the US. We've been going to Mexico the last few years, but I suppose you'd find them in the Caribbean as well. Food is already prepared, maid service, a pool for the little one to play in which more relaxing when watching over the little ones, but the beach is right there too. On-site daycare for your older kiddo, though be prepared for them to beg to stay and hang out with you (protip: put them in the daycare on the first day so they can make friends; most of the kids won't go to daycare every day, they'll be near their parents). Nighttime entertainment on-site if you're not all ready to pass out after dinner (though you most likely will).

I was 100% into the little beach cottage idea and 100% against some big all-inclusive before we went the first time, but my hubby booked it anyway. The next year he said "let's save a little $ and book a house". "Not on your effing life" I told him; it was experiencing the resort that made me realize that a little house would just be me cooking and cleaning in a different location, and it wouldn't be a real vacation at all.

(Fwiw, we've been booking at NOW properties in MX, but there's tons of similar resorts. We balance the room rate against what the pools and kids' amenities look like. More than just the company website or Yelp reviews, we go on youtube and watch videos that people have posted of their vacations at those properties; there's tons of said videos)
posted by vignettist at 8:59 AM on November 14, 2018 [4 favorites]

Seconding Puerto Rico. My son and his family went there a few years ago when their kids were 3 and 6, had a great time. Stayed in a hotel by a beach. If you do airbnb with three little kids you're gonna be constantly worrying about them breaking the owner's stuff. Also the house probably won't be babyproofed.
posted by mareli at 9:31 AM on November 14, 2018 [1 favorite]

another vote for an all inclusive in mexico if you can get your passports. Lots of times you can find one where kids "stay free", so until our kids reached 18 it was way less expensive than a beach house and flight to florida, and i am closer to florida than you are.

there are tons - barcelo maya south of playa del carman is very large but wonderful beach with huge pools. Don't stay at the high part called palace. beach isnt as nice there. I would pick the tropical/colonial section.

it will be warmer there than florida also.
posted by domino at 9:51 AM on November 14, 2018

Fort Lauderdale. I know the Westin on A1A has a Kid Club
Naples/Fort Myers (probably need to rent a car)
posted by TravellingCari at 10:01 AM on November 14, 2018

Maybe Padre Island? Could be touristy, but maybe less at that time of year.
posted by rhizome at 11:59 AM on November 14, 2018