The Ultimate Group Trip Guide to Key West: Where to Stay, Eat & Play
Where to Stay in Key West with a Large Group
When traveling as a group, accommodations can make or break your trip. The key is finding a place that offers plenty of space, privacy, and shared areas to gather.
Brightwild specializes in group-friendly stays that combine comfort, location, and local charm:
- Lunara Bay – A private waterfront collection of 26 luxury homes with pools, docks, and sweeping views. Perfect for weddings, reunions, and retreats, all just minutes from Old Town.
- Curry Mansion Inn – Historic elegance in the heart of Old Town with multiple rooms and spacious common areas. Ideal for wedding parties and group buyouts.
- Grand Maloney Hotel – Chic and intimate, this boutique hotel offers private buyout options for groups who want to be steps from Duval Street.
- Beachside Resort & Residences – Waterfront resort with spacious residences, a pool, meeting space, and on-site dining — great for families and business travelers
- KAMP Penthouse – A modern penthouse on Duval Street that sleeps up to 12 with a rooftop perfect for sunset gatherings.
The Ultimate Group Trip Guide to Key West: Where to Stay, Eat & Play
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Where to Stay in Key West with a Large Group
When traveling as a group, accommodations can make or break your trip. The key is finding a place that offers plenty of space, privacy, and shared areas to gather.
Brightwild specializes in group-friendly stays that combine comfort, location, and local charm:
- Lunara Bay – A private waterfront collection of 26 luxury homes with pools, docks, and sweeping views. Perfect for weddings, reunions, and retreats, all just minutes from Old Town.
- Curry Mansion Inn – Historic elegance in the heart of Old Town with multiple rooms and spacious common areas. Ideal for wedding parties and group buyouts.
- Grand Maloney Hotel – Chic and intimate, this boutique hotel offers private buyout options for groups who want to be steps from Duval Street.
- Beachside Resort & Residences – Waterfront resort with spacious residences, a pool, meeting space, and on-site dining — great for families and business travelers
- KAMP Penthouse – A modern penthouse on Duval Street that sleeps up to 12 with a rooftop perfect for sunset gatherings.
Where to Stay in Key West with a Large Group
When traveling as a group, accommodations can make or break your trip. The key is finding a place that offers plenty of space, privacy, and shared areas to gather.
Brightwild specializes in group-friendly stays that combine comfort, location, and local charm:
- Lunara Bay – A private waterfront collection of 26 luxury homes with pools, docks, and sweeping views. Perfect for weddings, reunions, and retreats, all just minutes from Old Town.
- Curry Mansion Inn – Historic elegance in the heart of Old Town with multiple rooms and spacious common areas. Ideal for wedding parties and group buyouts.
- Grand Maloney Hotel – Chic and intimate, this boutique hotel offers private buyout options for groups who want to be steps from Duval Street.
- Beachside Resort & Residences – Waterfront resort with spacious residences, a pool, meeting space, and on-site dining — great for families and business travelers
- KAMP Penthouse – A modern penthouse on Duval Street that sleeps up to 12 with a rooftop perfect for sunset gatherings.
Best Group-Friendly Restaurants in Key West
One of the joys of traveling with a group is sharing incredible meals together — and in Key West, you’ll find no shortage of memorable dining experiences. Here are some of our top picks for restaurants that can accommodate large parties while delivering on flavor and atmosphere:
- Tavern N Town – Located inside Beachside Resort & Residences, Tavern N Town is a local favorite for upscale dining with an approachable vibe. Their diverse menu — from prime steaks to seafood — and spacious seating make it ideal for group dinners.
- Bagatelle – Set in a historic home on Duval Street, Bagatelle serves elevated Key West cuisine with a Southern twist. Their brunch is legendary, and their upstairs balcony is perfect for a group meal with a view.
- Blue Heaven – A colorful and quirky Key West icon, Blue Heaven is famous for its laid-back atmosphere, roosters wandering the yard, and decadent key lime pie. Great for a casual group brunch or lunch.
- Hogfish Bar & Grill – Tucked away on Stock Island, Hogfish is a true local gem. The open-air setting and fresh-off-the-boat seafood make it perfect for a relaxed, authentic island meal with friends.
- Roostica – This cozy Italian spot on Stock Island is known for its wood-fired pizzas, hearty pasta dishes, and warm hospitality. The casual yet refined vibe makes it an excellent choice for group dinners.
- First Flight Island Restaurant & Brewery – Once the birthplace of Pan Am Airways, this historic building now houses a brewpub serving craft beers and island-inspired fare. Its indoor and outdoor spaces easily accommodate larger groups.
Top Excursions & Activities for Groups
Key West is a playground for groups — whether you’re looking for adventure, relaxation, or a little bit of both. Here are some of the best group-friendly experiences to add to your itinerary:
- Private Sunset Cruises – There’s nothing quite like watching the sun melt into the Gulf with your favorite people. Charter a catamaran or sailboat for your group and enjoy cocktails, music, and unbeatable views.
- Snorkeling & Sandbar Adventures – Spend the day exploring colorful coral reefs, spotting tropical fish, and relaxing on pristine sandbars. Many local charters offer private trips perfect for groups.
- Fishing Charters – Known as the “Sport Fishing Capital of the World,” Key West is a dream for anglers. Book a deep-sea trip for big game fishing or stay inshore for tarpon, snapper, and grouper.
- Private Yoga, Pilates, or HIIT Class with FYT Instructors – Start the day feeling energized with a group fitness session right at your rental, on the beach at Beachside, or in the gym. FYT’s certified instructors can tailor the workout for all levels, making it a fun and healthy way to bond as a group.
- Food & Cocktail Tours – Stroll through Old Town sampling conch fritters, Cuban sandwiches, craft cocktails, and island desserts while learning the island’s history.
- Kayaking & Paddleboarding – Explore hidden mangrove trails and shallow waters teeming with wildlife. Great for groups who want a low-key, nature-focused excursion.
- Island Bike Tours – Rent bikes for the whole group and cruise past pastel conch houses, quirky landmarks, and stunning waterfront views.
- Live Music & Nightlife on Duval Street – Key West’s nightlife is legendary. Start with sunset at Mallory Square, then hit everything from world-famous bars like Sloppy Joe’s to hidden speakeasies.
Tips for Planning a Seamless Group Trip
- Book Early – Key West is a popular destination year-round. Reserve accommodations, activities, and restaurants well in advance.
- Consider Transportation – Walking is easy in Old Town, but bikes, golf carts, and scooters make it even more fun.
- Balance Group & Free Time – Plan a few key activities together, but leave time for guests to explore independently.
- Use a Shared Itinerary – Keep everyone on the same page with a group chat or planning app.
Plan Your Group Stay with Brightwild
From intimate gatherings to large celebrations, Brightwild has the perfect property for your group in Key West. Our team can help arrange not just accommodations, but also activities, dining, and local experiences that make your trip unforgettable.
Ready to start planning? Explore our group-friendly Key West properties and let us help you host your best getaway yet. Start planning here.
Best Group-Friendly Restaurants in Key West
One of the joys of traveling with a group is sharing incredible meals together — and in Key West, you’ll find no shortage of memorable dining experiences. Here are some of our top picks for restaurants that can accommodate large parties while delivering on flavor and atmosphere:
- Tavern N Town – Located inside Beachside Resort & Residences, Tavern N Town is a local favorite for upscale dining with an approachable vibe. Their diverse menu — from prime steaks to seafood — and spacious seating make it ideal for group dinners.
- Bagatelle – Set in a historic home on Duval Street, Bagatelle serves elevated Key West cuisine with a Southern twist. Their brunch is legendary, and their upstairs balcony is perfect for a group meal with a view.
- Blue Heaven – A colorful and quirky Key West icon, Blue Heaven is famous for its laid-back atmosphere, roosters wandering the yard, and decadent key lime pie. Great for a casual group brunch or lunch.
- Hogfish Bar & Grill – Tucked away on Stock Island, Hogfish is a true local gem. The open-air setting and fresh-off-the-boat seafood make it perfect for a relaxed, authentic island meal with friends.
- Roostica – This cozy Italian spot on Stock Island is known for its wood-fired pizzas, hearty pasta dishes, and warm hospitality. The casual yet refined vibe makes it an excellent choice for group dinners.
- First Flight Island Restaurant & Brewery – Once the birthplace of Pan Am Airways, this historic building now houses a brewpub serving craft beers and island-inspired fare. Its indoor and outdoor spaces easily accommodate larger groups.
Top Excursions & Activities for Groups
Key West is a playground for groups — whether you’re looking for adventure, relaxation, or a little bit of both. Here are some of the best group-friendly experiences to add to your itinerary:
- Private Sunset Cruises – There’s nothing quite like watching the sun melt into the Gulf with your favorite people. Charter a catamaran or sailboat for your group and enjoy cocktails, music, and unbeatable views.
- Snorkeling & Sandbar Adventures – Spend the day exploring colorful coral reefs, spotting tropical fish, and relaxing on pristine sandbars. Many local charters offer private trips perfect for groups.
- Fishing Charters – Known as the “Sport Fishing Capital of the World,” Key West is a dream for anglers. Book a deep-sea trip for big game fishing or stay inshore for tarpon, snapper, and grouper.
- Private Yoga, Pilates, or HIIT Class with FYT Instructors – Start the day feeling energized with a group fitness session right at your rental, on the beach at Beachside, or in the gym. FYT’s certified instructors can tailor the workout for all levels, making it a fun and healthy way to bond as a group.
- Food & Cocktail Tours – Stroll through Old Town sampling conch fritters, Cuban sandwiches, craft cocktails, and island desserts while learning the island’s history.
- Kayaking & Paddleboarding – Explore hidden mangrove trails and shallow waters teeming with wildlife. Great for groups who want a low-key, nature-focused excursion.
- Island Bike Tours – Rent bikes for the whole group and cruise past pastel conch houses, quirky landmarks, and stunning waterfront views.
- Live Music & Nightlife on Duval Street – Key West’s nightlife is legendary. Start with sunset at Mallory Square, then hit everything from world-famous bars like Sloppy Joe’s to hidden speakeasies.
Tips for Planning a Seamless Group Trip
- Book Early – Key West is a popular destination year-round. Reserve accommodations, activities, and restaurants well in advance.
- Consider Transportation – Walking is easy in Old Town, but bikes, golf carts, and scooters make it even more fun.
- Balance Group & Free Time – Plan a few key activities together, but leave time for guests to explore independently.
- Use a Shared Itinerary – Keep everyone on the same page with a group chat or planning app.
Plan Your Group Stay with Brightwild
From intimate gatherings to large celebrations, Brightwild has the perfect property for your group in Key West. Our team can help arrange not just accommodations, but also activities, dining, and local experiences that make your trip unforgettable.
Ready to start planning? Explore our group-friendly Key West properties and let us help you host your best getaway yet. Start planning here.
The Ultimate Group Trip Guide to Key West: Where to Stay, Eat & Play
Where to Stay in Key West with a Large Group
When traveling as a group, accommodations can make or break your trip. The key is finding a place that offers plenty of space, privacy, and shared areas to gather.
Brightwild specializes in group-friendly stays that combine comfort, location, and local charm:
- Lunara Bay – A private waterfront collection of 26 luxury homes with pools, docks, and sweeping views. Perfect for weddings, reunions, and retreats, all just minutes from Old Town.
- Curry Mansion Inn – Historic elegance in the heart of Old Town with multiple rooms and spacious common areas. Ideal for wedding parties and group buyouts.
- Grand Maloney Hotel – Chic and intimate, this boutique hotel offers private buyout options for groups who want to be steps from Duval Street.
- Beachside Resort & Residences – Waterfront resort with spacious residences, a pool, meeting space, and on-site dining — great for families and business travelers
- KAMP Penthouse – A modern penthouse on Duval Street that sleeps up to 12 with a rooftop perfect for sunset gatherings.
Best Group-Friendly Restaurants in Key West
One of the joys of traveling with a group is sharing incredible meals together — and in Key West, you’ll find no shortage of memorable dining experiences. Here are some of our top picks for restaurants that can accommodate large parties while delivering on flavor and atmosphere:
- Tavern N Town – Located inside Beachside Resort & Residences, Tavern N Town is a local favorite for upscale dining with an approachable vibe. Their diverse menu — from prime steaks to seafood — and spacious seating make it ideal for group dinners.
- Bagatelle – Set in a historic home on Duval Street, Bagatelle serves elevated Key West cuisine with a Southern twist. Their brunch is legendary, and their upstairs balcony is perfect for a group meal with a view.
- Blue Heaven – A colorful and quirky Key West icon, Blue Heaven is famous for its laid-back atmosphere, roosters wandering the yard, and decadent key lime pie. Great for a casual group brunch or lunch.
- Hogfish Bar & Grill – Tucked away on Stock Island, Hogfish is a true local gem. The open-air setting and fresh-off-the-boat seafood make it perfect for a relaxed, authentic island meal with friends.
- Roostica – This cozy Italian spot on Stock Island is known for its wood-fired pizzas, hearty pasta dishes, and warm hospitality. The casual yet refined vibe makes it an excellent choice for group dinners.
- First Flight Island Restaurant & Brewery – Once the birthplace of Pan Am Airways, this historic building now houses a brewpub serving craft beers and island-inspired fare. Its indoor and outdoor spaces easily accommodate larger groups.
Top Excursions & Activities for Groups
Key West is a playground for groups — whether you’re looking for adventure, relaxation, or a little bit of both. Here are some of the best group-friendly experiences to add to your itinerary:
- Private Sunset Cruises – There’s nothing quite like watching the sun melt into the Gulf with your favorite people. Charter a catamaran or sailboat for your group and enjoy cocktails, music, and unbeatable views.
- Snorkeling & Sandbar Adventures – Spend the day exploring colorful coral reefs, spotting tropical fish, and relaxing on pristine sandbars. Many local charters offer private trips perfect for groups.
- Fishing Charters – Known as the “Sport Fishing Capital of the World,” Key West is a dream for anglers. Book a deep-sea trip for big game fishing or stay inshore for tarpon, snapper, and grouper.
- Private Yoga, Pilates, or HIIT Class with FYT Instructors – Start the day feeling energized with a group fitness session right at your rental, on the beach at Beachside, or in the gym. FYT’s certified instructors can tailor the workout for all levels, making it a fun and healthy way to bond as a group.
- Food & Cocktail Tours – Stroll through Old Town sampling conch fritters, Cuban sandwiches, craft cocktails, and island desserts while learning the island’s history.
- Kayaking & Paddleboarding – Explore hidden mangrove trails and shallow waters teeming with wildlife. Great for groups who want a low-key, nature-focused excursion.
- Island Bike Tours – Rent bikes for the whole group and cruise past pastel conch houses, quirky landmarks, and stunning waterfront views.
- Live Music & Nightlife on Duval Street – Key West’s nightlife is legendary. Start with sunset at Mallory Square, then hit everything from world-famous bars like Sloppy Joe’s to hidden speakeasies.
Tips for Planning a Seamless Group Trip
- Book Early – Key West is a popular destination year-round. Reserve accommodations, activities, and restaurants well in advance.
- Consider Transportation – Walking is easy in Old Town, but bikes, golf carts, and scooters make it even more fun.
- Balance Group & Free Time – Plan a few key activities together, but leave time for guests to explore independently.
- Use a Shared Itinerary – Keep everyone on the same page with a group chat or planning app.
Plan Your Group Stay with Brightwild
From intimate gatherings to large celebrations, Brightwild has the perfect property for your group in Key West. Our team can help arrange not just accommodations, but also activities, dining, and local experiences that make your trip unforgettable.
Ready to start planning? Explore our group-friendly Key West properties and let us help you host your best getaway yet. Start planning here.
