The white picket fence with pineapple cutouts is a charming and classic element often seen in Key West and other parts of the South. This type of fence design combines the traditional appeal of a white picket fence with the tropical motif of pineapples. Here are a few points to consider:

1. **Symbolism:** Pineapples are often associated with hospitality and a welcoming spirit. The use of pineapple cutouts in the fence design may symbolize a warm and inviting atmosphere, which is fitting for the tropical and friendly environment of Key West.

2. **Aesthetic Appeal:** The combination of a white picket fence and pineapple cutouts adds a touch of whimsy and character to the landscape. The contrast between the white fence and the intricate pineapple shapes can create a visually pleasing and distinctive look.

3. **Tropical Flair:** Pineapples are tropical fruits, and their incorporation into the fence design reinforces the tropical theme of Key West. The design choice reflects the island's unique blend of Southern, Caribbean, and Floridian influences.

4. **Common in Residential Areas:** You may come across such fences in residential neighborhoods, where homeowners use them to add a personal touch to their properties. The design aligns with the relaxed and cheerful ambiance of Key West.

5. **Landscaping and Gardens:** The fence might surround a garden or landscaped area, enhancing the overall appeal of the outdoor space. Pineapple motifs can extend to other elements of the landscaping, creating a cohesive and themed look.

6. **Local Craftsmanship:** Many of these fences are crafted with attention to detail, showcasing the craftsmanship of local artisans. The use of pineapple cutouts is a decorative choice that adds a touch of individuality to the fence design.

Keep in mind that fence designs can vary, and not every white picket fence in Key West will feature pineapple cutouts. However, if you're exploring residential areas or gardens in Key West, you might come across this delightful and symbolic design that contributes to the island's unique charm. It's one of the many elements that make Key West's architecture and landscaping distinct and appealing.