Monday Key Tours
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Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,203, price is now $793 per person
$793
per person
Jul 11 - Jul 15
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,261 reviews)
Upon an early arrival, we found our bungalow was clean and ready! The front desk staff was friendly with a sense of humor. We immediately headed to the pool bar with our welcome drink tokens and found the bartender just as welcoming!
Winslow’s Bungalows is situated in a perfect location as we could walk to the Southernmost point in about 10 minutes, or Mallory Square in 15 min.
Key West never disappoints and we loved the Songwriters Festival!
Reviewed on May 8, 2026
Hyatt Vacation Club at Windward Pointe, Key West
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Price was $1,506, price is now $953 per person
$953
per person
Jul 11 - Jul 15
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,059 reviews)
The hidden resort fees were absolutely ridiculous! $40 a day, plus $5 a day plus $150 coverage without any explanation. This property is located directly next to the airport and they do not provide a shuttle service to pick you up. We used Uber for everything, another extra expense. ( The Hampton Inn next door had a shuttle that went everywhere)
Reviewed on May 5, 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Old Town Key West
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Price was $1,524, price is now $972 per person
$972
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (365 reviews)
Stayed in a one bedroom unit. Good size kitchen/living room, however bathroom was tiny. Bedroom was ok.. lots of closet/storage, however bed could have been bigger.
Location was awesome… just a couple blocks to everything!
Reviewed on May 6, 2026
Browse tours and tickets to explore Monday Key
Tours & day trips
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Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Activity duration is 16 hours and 30 minutes
8.8 out of 10 with 22 reviews
Wildlife & nature
See all 47 activities
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Activity duration is 3 hours
9.4 out of 10 with 155 reviews
Free cancellation available
History & culture
See all 46 activities
Key West Conch Tour Train
Activity duration is 1 hour
8.8 out of 10 with 137 reviews
Free cancellation available
Private & custom tours
See all 21 activities
Dry Tortugas National Park Day Trip by Luxury Private Boat
Activity duration is 8 hours
Free cancellation available
Classes & workshops
See all 8 activities
Florida: Sunset Champagne Cruise on the Marathon Mermaid
Activity duration is 2 hours
10.0 out of 10 with 12 reviews
Free cancellation available
Popular places to visit
Key West Naval Station
After visiting Key West Naval Station, make a plan to see the other sights and activities in Key West. Experience the area's great live music and lively festivals.
Stock Island Yacht Club & Marina
Explore the waterfront of Stock Island Yacht Club & Marina and enjoy activities such as boating in Key West. Discover the area's beautiful sunsets and lively bars.
Key West Golf Club
Play a round of golf in Key West at Key West Golf Club, and enjoy other activities such as boating. Amble around the area's seaside or seek out the biking trails.
Robbie's
Explore the waterfront of Robbie's and enjoy activities such as boating in Key West. Wander the seaside and beautiful beaches in the area.
Key West Tropical Forest and Botanical Garden
Enjoy the beautiful sunsets and explore Key West Tropical Forest and Botanical Garden, a lovely green space in Key West. Stroll along the area's seaside or experience its lively festivals.
Boca Chica Beach
Why not spend a lazy afternoon at Boca Chica Beach during your trip to Key West? Stroll along the area's seaside, or simply savor its lively bars.
Best Lodging Options Near Monday Key
Check availability on hotels close to Monday Key
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Tidelands House at Lunara Bay
Key West FL
Seagate House by Brightwild Waterfront w Dock
Key West FL
Suncoast House at Lunara Bay
Key West FL
The Greenmoor House at Lunara Bay
Key West FL
The Seagate Estate at Lunara Bay
Key West FL
Altair House at Lunara Bay
Key West FL
Larkshine House at Lunara Bay
Key West FL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.