St. Augustine in Winter: Where to Stay

October 11, 2025 By John McNamara

St. Augustine in Winter: Where to Stay for Couples (and Families)

Historic District • Anastasia Island • Butler & Crescent Beach

Why Winter in St. Augustine Works

When winter rolls in, St. Augustine glows—literally. From mid-November through January, the Nights of Lights turn the nation’s oldest city into a lantern-lit postcard. Cooler temps mean easy strolling, cozy dinners, and beach walks without the summer crowds. This guide focuses on mid-range stays for couples first, with easy tweaks for families, across three great bases: the walkable Historic District, Anastasia Island/St. Augustine Beach, and the quieter sands of Butler and Crescent Beach that is close to the swim with the dolphins program.

Area 1: Historic District (Walkable & Romantic)

If your picture of St. Augustine includes brick streets, Spanish architecture, and twinkle lights—this is it. You’ll be steps from St. George Street, Castillo de San Marcos, wine bars, and carriage rides. Parking can be tight, but once you’re here, you won’t need the car much.

Best For

• Couples: ambiance, dining, and sightseeing outside the front door
• Families: convenience and stroller-friendly streets

Where to Stay (Mid-Range, by Property Style)

Boutique Inn / B&B (couples-first)

• St. George Inn — Boutique rooms right on St. George Street; intimate and convenient.
• The Collector Luxury Inn & Gardens (Adults Only) — Nine restored historic houses, heated pool, and garden paths.
• Cedar House Inn — Classic B&B charm with thoughtful touches and a cozy, adults-forward vibe.

Family Hotel (walkable + practical)

• DoubleTree by Hilton St. Augustine Historic District — Near the Old City Gate; pool and on-site dining.
• Hilton St. Augustine Historic Bayfront — Bayfront address steps from the Spanish Quarter.
• Sebastian Hotel — Suite-style rooms along the San Sebastian River; handy for families.

Waterfront/Bayfront (great views, not oceanfront)

• Bayfront Inn — Small hotel on Matanzas Bay; parking and breakfast make it easy.
• Best Western Historic Bayfront — Budget-friendly bayfront option within the Historic District.

Winter Itinerary Notes

• Nights of Lights: Go after dusk on a weekday; book a harbor cruise or trolley lights tour for photos.
• Cozy dining: Reserve a courtyard table with heaters; follow with a tucked-away speakeasy.
• Rain plan: Museums (Lightner, Flagler College tour, Pirate & Treasure), plus wine or chocolate tastings.

Area 2: Anastasia Island / St. Augustine Beach (Ocean Air, Laid-Back Days)

Cross the Bridge of Lions and you’re on Anastasia Island, home to St. Augustine Beach, Anastasia State Park, and family-friendly eateries. You’re 10–12 minutes from downtown, but your vibe is salt air and sandy shoes.

Best For

• Couples: beach walks by day, downtown date nights
• Families: space to spread out, easy beach parking

Where to Stay (Mid-Range, by Property Style)

Beachfront Resort (steps to the sand)

• Embassy Suites by Hilton St. Augustine Beach Oceanfront Resort — Oceanfront balconies, heated pool, and breakfast.
• Guy Harvey Resort St. Augustine Beach — Beachfront pool, casual dining, on-site rentals.
• Beachfront Bed & Breakfast (Adults Only) — Romantic B&B directly on the sand.

Boutique Inn / Small Hotels (island charm)

• Conch House Marina Resort — Tropical, marina-side setting with a lively lounge.
• Anastasia Inn — Simple, well-located base between beach and downtown; solid value.

Family Hotel (easy wins)

• Edgewater Inn — At the foot of the Bridge of Lions; pool, breakfast, and quick hop downtown.
• Guy Harvey Resort St. Augustine Beach — Also great for families; beachfront access and activities.

Winter Itinerary Notes

• Beach walks: Cooler temps = longer, comfortable strolls; pack a light jacket.
• State park day: Kayaks, trails, and shelling at Anastasia State Park.
• Date night downtown: Rideshare over the bridge; skip parking stress and just enjoy the lights.

Area 3: Butler & Crescent Beach (Quiet Shores, Big-Sky Sunrises)

South of St. Augustine Beach, Butler and Crescent Beach deliver wide, peaceful sands and low-rise complexes. It’s slower, quieter, and wonderfully restorative—still just 15–20 minutes from the Historic District.

Best For

• Couples: privacy, sunrise coffee on the balcony
• Families: room for sandcastles, bikes, and naps between outings

Where to Stay (Mid-Range, by Property Style)

Beachfront Resort / Condo-Resort

• Beacher’s Lodge Oceanfront Suites (Crescent Beach) — Condo-hotel with kitchenettes and a beachfront pool.
• Hibiscus Oceanfront Resort / Ocean Gate at Hibiscus (Butler Beach) — Condo resort with multiple pools and hot tubs.
• Ocean House Condominiums (Crescent Beach) — Spacious oceanfront condos with large balconies.

Condo Communities (space for couples or families)

• Crescent Sandpiper (Crescent Beach) — Beachfront complex; many units with ocean views.
• Ocean Village Club (Butler Beach) — Popular community with pools; a variety of unit types and layouts.

Winter Itinerary Notes

• Sunrise & coffee: Quiet sands make for slow, romantic mornings.
• Day trips: Ten minutes to island dining; twenty minutes to downtown lights.
• Rain plan: Lighthouse & Maritime Museum (weather-dependent zip line) or cozy condo game time.

How to Choose Your Base (Couples vs. Families)

Couples

• Historic District: romance, car-free evenings, Christmas lights at your doorstep
• Anastasia Island: beach mornings + downtown date nights
• Butler/Crescent: privacy, porch wine, and sunrise walks

Families

• Anastasia Island: pools, pier, and fast drives to attractions
• Historic District: strollers + trolleys beat car seats + parking hunts
• Butler/Crescent: bigger floor plans and nap-friendly afternoons

Winter Packing & Planning Tips

• Layers, not parkas: Light sweaters by day; breezy evenings on the bay.
• Advance reservations: Nights of Lights draws crowds—book lodging, dinners, and tours early.
• Parking strategy: Downtown—confirm on-site parking or garage options. Beach days—arrive before brunch.
• Trolley passes: Hop-on/hop-off keeps everyone happy and rested.
• Rain alternatives: Museums, tasting rooms, Flagler College tour, and cozy coffee shops.

Sample 3-Day Winter Plan (Mid-Range)

Day 1 – Historic Heart

• Check in, early dinner, and an evening trolley lights tour
• Nightcap at a speakeasy or cocoa on a bayfront bench

Day 2 – Island & Lighthouse

• Breakfast by the pier, long walk at Anastasia State Park
• Climb the Lighthouse for golden hour
• Rideshare downtown for tapas and twinkle-light photos

Day 3 – Beach & Brunch

• Butler/Crescent Beach sunrise and shell hunt
• Brunch on A1A, souvenir stop, and a final stroll through the Plaza lights
• Or Go Swim with Dolphins on St Augustine beach.

For Travel Agents (and DIY Planners)

Booking Cues (Mid-Range)

• Historic District: boutique inns with breakfast and on-site parking; ask about holiday packages
• Anastasia: oceanfront hotels with heated pools; request balcony or partial-ocean categories for value
• Butler/Crescent: condo resorts with flexible minimums; top-floor or corner units for views

Add-On Experiences

• Nights of Lights harbor cruise (blankets often provided)
• Lighthouse climb and museum (consider timed entry)
• Chocolate or wine tasting tours for cozy afternoons
• Marineland dolphin encounters (book ahead for daytime fun)

Cancellation & Flexibility

• Winter is popular but calmer than summer—aim for 48–72-hour policies and watch holiday blackout dates.

Bottom Line

• Historic District = romance and lights
• Anastasia Island/St. Augustine Beach = ocean air + easy downtown nights
• Butler & Crescent Beach = quiet, space, and sunrise therapy

Pick the vibe that fits, lock in a mid-range property style, and let St. Augustine’s winter magic do the rest.