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Group Stays at Winslow's Bungalows
With three pools, winding pathways, and the lively Bungalow Bar, Winslow’s Bungalows makes it easy for groups to turn a Key West getaway into time spent together. From wedding weekends and milestone celebrations to reunions and friends’ trips, the property offers the flexibility for everyone to stay close while still having room to make the weekend their own.
At a Glance
Perfect for: Larger Room Blocks · Wedding Weekends · Welcome Gatherings · Milestone Celebrations · Group Getaways
Room Blocks: 10–40 Rooms Per Night
Elizabeth Estate: Exclusive 11-Room Buyout · Accommodates Up to 22 Overnight Guests
Private Gatherings: Poolside Events for Up to 30 Guests with Exclusive Elizabeth Estate Buyout
Events: Up to 50 Guests
Elizabeth Estate
a House for the Whole Crew
Bring everyone together with an exclusive buyout of The Elizabeth Estate at Winslow’s Bungalows. Featuring 11 king guest rooms, a private pool, and a secluded sun deck, the estate gives your group the space and privacy of a vacation home paired with the amenities and hospitality of a boutique hotel.
Designed for wedding weekends, milestone celebrations, family reunions, retreats, and getaways with friends, the estate becomes entirely yours. Just beyond it, your group can enjoy the full Winslow’s Bungalows experience, including two additional pools, complimentary breakfast, The Bungalow Bar, live music, and everything you need for a memorable stay in Key West.
Entire House
A standalone section of Winslow’s Bungalows designed for groups to stay together while enjoying their own space.
Private Pool
At the heart of your stay, a private pool creates a space exclusively for your group to gather, unwind, and celebrate.
Space to Gather
Host a welcome party, plan a catered gathering, or simply spend the afternoon poolside together.
Elizabeth Estate Rooms
Housed within one historic building, The Elizabeth Estate brings your entire group together while still giving everyone a space of their own. Eleven king guest rooms pair original Key West character with thoughtfully designed interiors, creating an easy flow between time spent together and time to unwind. Step outside to gather by your private pool and sun deck, then retreat to the comfort of your own room at the end of the day.
- 11 Private Guest Rooms
- Accommodates 22 people
- Full Access to Winslow’s Bungalows Amenities
A Little Above It All
treehouse suite
Perched three stories up and reached by three flights of stairs, the Treehouse Suite is a hideaway made for slowing down. Its tucked-away setting offers a little extra space from the energy of Key West, while keeping the best of Old Town close at hand. Perfect for honeymoons, romantic escapes, special occasions, or group guests who appreciate a quiet place to retreat at the end of the day.
- 600 sq/ft
- 1 King Bed
- 2 People
Wedding Weekends
Make Winslow’s Bungalows the home base for your Key West wedding weekend. With three pools, The Bungalow Bar, inviting gathering spaces, and room blocks that keep everyone close, it’s a natural setting for the moments surrounding “I do.” Welcome your guests over cocktails, spend the morning getting ready together, and come back for a farewell brunch or one last afternoon by the pool.
Wedding Room Block Enhancements
- Preferred accommodations for the couple
- Welcome parties and pre-wedding gatherings
- Farewell brunches and poolside gatherings
- Getting-ready spaces with food and beverage options
- Welcome bag delivery or placement at check-in
- Personalized booking link for wedding guests
- Access to preferred Key West vendor recommendations
- Special first-anniversary stay offer for the couple
Food and Drink
Start the weekend with cocktails and small bites by the pool, gather around the table for a rehearsal dinner, or bring everyone back together over brunch the next morning. Menus can move from passed bites and grazing boards to full dinners and leisurely brunches, with beer and wine, full bar service, and signature cocktails to match.
Gather & Celebrate
There are birthdays, and then there are birthdays in Key West. Milestone celebrations, family reunions, executive retreats, bachelor and bachelorette weekends, girls’ trips, guys’ getaways, and long-overdue gatherings with friends all feel a little different when everyone escapes to the island together.
At Winslow’s Bungalows, the occasion becomes more than a single night. Welcome cocktails turn into afternoons by the pool, catered gatherings give way to evenings out in Old Town, and farewell brunches stretch the celebration just a little longer. The best part? There’s no one way to do it. Here’s a little inspiration for what your group getaway could look like.
