Hotel

Question

What is recommended hotel for a family of 4 with 2 boys age 10 either in longboat key, Anna Maria island, or Sarasota. I am not familiar with this area in Florida. We are looking for a very nice hotel, family friendly, pool, and on beach. Would love to be able to walk to restaurants if possible.

Answer

If you’re looking for a very nice, family-friendly hotel for your family of 4 (with two 10-year-old boys) along the Gulf Coast in the Sarasota / Anna Maria / Longboat Key area, here are some great options depending on how high end you want to go and how much “beach resort feel” matters.

Here are recommended hotels / resorts by area:

The St. Regis Longboat Key Resort (Longboat Key) — This is a top-tier luxury resort with one- to four-bedroom suites, private terraces, a dedicated saltwater lagoon, a pool with cabanas, and a truly private beach. Great for families who want space, elegance, and service.
Resort at Longboat Key Club — More moderately luxurious, this resort is very family friendly. It offers a large beach, comfortable pool, and a kids’ program (Camp Loggerhead). There are suites with kitchens, so it’s great for families.
Little Gull Cottages (Longboat Key) — A charming, cottage-style resort. It’s smaller, more intimate, with a heated pool, direct beach access, and amenities like bikes — perfect if you want a boutique place that feels like a home away from home.
Anna Maria Beach Resort (Anna Maria Island, Holmes Beach) — A very family-friendly resort with spacious suites or condo-style rooms, kitchens or kitchenettes, a large resort pool, and private beach access.
Waterline Villas & Marina (Anna Maria Island) — If you’re okay with a villa setup, these two-bedroom waterfront condos are excellent. Full kitchens, a resort-style pool, boat marina, and a calm, upscale feel make this ideal for families wanting modern space plus proximity to water-based activities.
Mainsail Beach Inn (Anna Maria Island) — More economical than some of the resorts, but still very comfortable. Upscale two- and three-bedroom residences, many with balconies or decks, and direct beach access.

### My Top Picks for Your Family:

- If you want a full luxury resort with everything: Go with St. Regis Longboat Key. - If you want family-friendly amenities at a more moderate luxury level: Longboat Key Club is perfect. - If you want charm + cottages + a laid-back feel: Little Gull Cottages. - If you want to be on Anna Maria Island with room to spread out: Anna Maria Beach Resort or Waterline Villas are ideal.

### Other Tips:

Book early: These places, especially the family-friendly resorts, fill up quickly in summer.
Check room layouts: For a family of 4, make sure the room or suite has enough beds or a pull-out sofa + separate bedroom.
Consider whether having a kitchen is important: Some of these places offer full kitchens, which helps with meals and snacks for kids.
Look at transportation: If you plan to explore Sarasota, having a car is great, but on the islands (Longboat / Anna Maria) you might mix driving with biking or walking.

All of these hotels offer beach access, pools, and a relaxing environment that works well with children — especially your boys, so you should be able to enjoy both downtime and fun during your stay.