Key West Deals for Spring 2023

Shake off the winter and get a jump start on beach season with these hotel offerings in Florida’s Conch Republic

Closer to Cuba than Miami, Key West is full of history and cultural influences from Havana and the Bahamas. Architecture, cuisine, and diverse cultures are represented in Old Town Key West and many resorts reflect the Caribbean style with outdoor spaces, balconies, and porches. Here, you’ll find warm tropical nights and days filled with nature, outdoor activities, and plenty of on-the-water sports. Now that the snowbirds are gone, it’s time to take advantage of these deals and enjoy this subtropical paradise before the summer rush moves in.

Pier House Resort & Spa

This iconic Key West charmer sits right in town close to everything yet feels far removed from the sometimes- boisterous streets of downtown Key West. When guests are out on the deck facing the beach and water, there is a relaxed vibe you would have found throughout Key West years ago. It’s the only spot in town with a sandy beach and the luxurious resort is full service with a spa, fitness center, pool, two restaurants, and one of the best and most eclectic bars in Key West. Save 10% on Dockside Suites and Harbor View rooms. For more info:

Pier House Bar Key West

The nautical-inspired bar at the Pier House; a stop at Chart Room unveils tales and memorabilia. Photo: Pier House

Southernmost Beach Resort

Situated along the southern limit of the famed Duval Street in Key West, the award-winning resort features a tropical, warm, and cozy feel, while ocean views abound. Recently renovated, the resort features a modern sleek design and classic coastal charm. Amenities include a full-service spa, group fitness classes, three heated pools, two white sand beaches, and live entertainment. There are also cocktail tastings and painting classes to round out your time at the Southernmost Beach Resort. Book the April Fools’ Sale and save up to 35% off plus receive a $35 food and beverage credit. Good for travel in 2023 but with a limited time for booking. For more info:

Southernmost Hotel Key West

Southernmost Beach Resort is close enough to the ocean for endless sea views and sandy beaches. Photo: Southernmost Beach Resort

The Perry Hotel & Marina

Set in the Stock Island Marina Village, this boutique waterfront hotel combines a touch of Old Key West with an upscale and ultra-modern vibe. There are two dockside restaurants. Matt’s Stock Island and Salty Oyster, the relaxed come-as-you-are outdoor restaurant and bar. Beyond the waterfront pool, guests have water sports and bike rentals on-site, and if you need a ride to town, there’s a scheduled shuttle. Save 25% when you book at least 14 days in advance or for that long weekend away with a dose of sunshine you can save up to 20% for three nights or more. To book:

Perry Hotel Key West

Some rooms at the Perry Hotel have wrap-around balconies overlooking the pool and marina. Photo: The Perry Hotel


With spaces created to encourage mingling and modular rooming options that can handle singles, couples, and groups, this is certainly Not Your Average Hotel (NYAH). Bring some friends (adults only) and you can split the cost in a variety of bedded rooms from a room with six single beds, a king and two singles, or book the cottage with one king bed. There are three pools and one Jacuzzi and plenty of lounging chairs. A daily amenity fee of $34.99 includes Continental breakfast, Starbucks coffee, and tea 24 hours, and WIFI. Guests can also take part in a happy hour from 4:20 pm to 5:20 pm or head out to explore, a bike rental is on site. Stay for four nights or more and save 20%. For more info:

NYAH Key West

The entrance to NYAH was built in the traditional Key West style with a large front porch. Photo: NYAH

Havana Cabana

You’ll be immersed in Cuban Culture—the spirit, the art, the music, the cars—when you vacation at Havana Cabana. Choose between rooms with either a pool view or gulf view or the larger Havana rooms. When hunger strikes there’s Cuban cuisine at the Floridita Food Truck where breakfast, lunch, and dinner are served under a thatched roof patio. Visit the Mojitos Pool Bar if you’re needing your minty mid-day mojito. The resort offers a variety of daily activities like morning happy hour or off-site excursions. Book the Spring break special offer by April 16, 2023, and save 25% off your room rate. To book:

Havana Cabana Key West

Interiors of rooms at Havana Cabana showcase décor and paraphernalia you might find in Cuba. Photo: Havana Cabana