The 8 BEST Hotels for Large Groups in Key West 2026
Explore group-friendly Key West stays suited to reunions, celebrations, and getaways. Finding Key West hotels that can comfortably host a large group takes careful planning. This list highlights stays with space, useful amenities, and convenient locations.
1500 Reynolds Street, Key West
A historic resort with grand ballrooms and beachfront gathering space. A ballroom that welcomes up to 530 people and an oceanfront event lawn give big celebrations room to unfold. Dedicated event professionals can help bring everyone together for shared meals and island activities. The Ernest Hemingway Home and Museum is about a 20-minute walk away, and Duval Street is roughly a 7-minute drive. For a group celebration with a grand, beachfront feel, Casa Marina makes the gathering part of the trip.
245 Front Street, Key West
Waterfront event spaces welcome gatherings of up to 300. Flexible waterfront venues can host gatherings of up to 300, whether you’re planning a reunion or a larger celebration. A dedicated planning team and on-site dining make it easy to bring your group together between island outings. The Key West Aquarium is next door, and Duval Street is about a 6-minute walk. It’s a lively Old Town stay for groups who want their shared plans close at hand.
1435 Simonton Street, Key West
Private beach and event spaces for groups up to 311. A private beach, oceanfront lawns, and flexible indoor venues give your group plenty of room to gather, with event spaces for up to 311 people. Room blocks and dedicated planning support help keep a larger trip feeling connected. The Ernest Hemingway Home and Museum is about a 10-minute walk away, while Duval Street is around 15 minutes on foot. It’s a relaxed beachfront pick for groups who want celebration space with Old Town close by.
2801 North Roosevelt Boulevard, Key West
Three-bedroom villas give friends and family space together. Three-bedroom villas sleep a group across separate rooms, with a living room where you can catch up between outings. Flexible event spaces and leafy pool areas give reunions and celebrations a relaxed island setting. Smathers Beach is about a 10-minute drive away, and a complimentary shuttle connects you with Duval Street. It’s a sociable, easygoing stay for groups who value shared villa space as much as time together outdoors.
3841 North Roosevelt Boulevard, Key West
Spacious multi-bedroom residences make group time feel easy. One- and two-bedroom residences give your group room to spread out, with select stays offering full kitchens and living and dining areas. A pool, private beach area, and complimentary shuttle add easy ways to meet back up after exploring. Key West International Airport is less than 2 km away, and a free shuttle runs to the city center. It’s a laid-back choice for friends or families who want a little more shared living space.
5950 Peninsular Ave, Key West
A 111-slip marina and waterfront event spaces set the scene. With 175 rooms and group room blocks, this waterfront resort can keep a sizable party close together. Its marina-side event spaces and pool give your crew places to gather between meals and water activities. The Key West International Airport is about a 5-minute drive away, and Duval Street is about a 20-minute drive. It suits groups who want a resort-style meetup with boating and time by the water built in.
2001 South Roosevelt Boulevard, Key West
Two-bedroom suites and flexible spaces suit group getaways. Two-bedroom suites give friends or family a comfortable way to share a stay while keeping separate sleeping spaces. Flexible event areas make room for group celebrations, and the pool brings everyone together for downtime. Smathers Beach is just across South Roosevelt Boulevard, and a shuttle connects the resort with Old Town. It’s a casual, beach-minded stay for groups who like having space to gather and unwind.
601 Front Street, Key West
Harbor-view event rooms bring groups together in Old Town. Flexible meeting rooms and an event dock give your group several waterfront settings for a shared occasion. A poolside bar and two on-site restaurants make it easy to gather for a meal or a relaxed drink. Duval Street is about a 3-minute walk away, and Mallory Square is roughly a 10-minute walk. It’s a lively choice for groups who want event space and Old Town outings within easy reach.
Frequently Asked Questions
What are the best hotels in Key West for accommodating large groups?
Some of the top choices for large groups include the Southernmost Beach Resort, which offers multiple room types and extensive amenities, and the Ocean Key Resort & Spa, known for its spacious suites with stunning views.
Are there hotels in Key West that offer group discounts?
Yes, many hotels provide group discounts for bookings of five rooms or more. It is advisable to contact the hotel directly to inquire about available packages and offers for your group.
Which hotels in Key West have easy access to group activities?
The Margaritaville Key West Resort & Marina is conveniently located near popular group activities like boating and fishing. The hotel can also assist with arranging group tours and excursions.
Can large groups find hotels with kitchen facilities in Key West?
Yes, several hotels and resorts, such as the Sunset Key Cottages, offer kitchen facilities or full kitchens in their accommodations, making it easier for large groups to prepare meals together.
Which hotels in Key West provide meeting or event spaces for large groups?
The Key West Marriott Beachside Hotel features a large conference center as well as outdoor spaces ideal for group events. The team can help facilitate meetings or gatherings while you enjoy your stay.
Are there family-friendly hotels in Key West suitable for large groups?
The Hilton Garden Inn Key West is a family-friendly option that provides spacious rooms and amenities like a pool and on-site dining, catering well to families traveling in larger groups.
What hotels in Key West are close to nightlife for groups looking to explore?
The Hyatt Centric Key West Resort & Spa is located near Duval Street, which is known for its vibrant nightlife. Staying here allows groups to easily access bars, restaurants, and live music venues.
Can hotels in Key West assist with transportation for large groups?
Many hotels, such as the Reach Key West, can help organize transportation for large groups, including shuttle services to and from the airport or other local attractions.
Are there hotels with outdoor spaces for group gatherings in Key West?
Yes, the Pier House Resort & Spa offers beautiful outdoor spaces, including a beach area and a pool deck, which are perfect for group gatherings, barbeques, or just relaxing together.
What is the best time of year for large groups to visit Key West?
The best time for large groups to visit Key West is during the shoulder seasons of spring (March to May) and fall (September to November) for pleasant weather and fewer crowds, making it easier to book accommodations.
