Spend April your way: A curated guide to slow travel, culture & comfort in Key West

Why extended stays shine in spring

A 30-day stay isn’t just a longer vacation — it’s a lifestyle shift. Many of our spring guests work remotely, try out the idea of “living in Key West,” or simply want a home where they can settle in, cook meals, host friends, and join the rhythm of local life.

Our concierge team plays an important role: arranging snorkel trips, private charters, eco-adventures, museum tours, bike rentals, spa appointments, dining reservations, and more. Spring travelers particularly love curated itineraries that blend outdoor adventure with quiet relaxation.

Where comfort & character meet

• Azur Palm: Perfect for couples looking for a romantic, upscale home with ocean views and a beach in an exclusive, gated community with 2 pools. This recently renovated, 2BR, 2BA condo offers two ensuite baths and a beautiful living area that looks directly out to a sea of blue. You simply can’t find a more peaceful waterfront retreat in Key West.
• The Pink House: This two-story, open-concept Conch-style home is tucked into the historic Bahama Village neighborhood. Just 3 blocks from Duval Street and north of Truman Avenue in Historic Old Town, the location allows guests to enjoy the best of Key West on foot. With two first floor living rooms, two ensuite bedrooms and two private balconies, everyone can enjoy their own slice of heaven.

Extended-stay guests love April!

Some of the island’s most unique annual events happen in springtime, perfect for extended-stay guests who want to immerse themselves in Key West culture:

• Conch Republic Independence Celebration: The 44th annual  celebrates the Conch spirit and takes place from April 17-26.
• Viking Yachts Key West Challenge: Multiple events and gatherings take place from April 8-12, at Dante's Tiki Bar, 700 Front St.
• 30th annual Key West Songwriters Festival: This spirited festival takes over the island from April 29–May 3, uniting more than 200 renowned and rising songwriters for over 60 unforgettable shows.

Your month of slow island living awaits

Why not extend the spring break mindset into something far better — an entire month of living like a local in Key West. Instead of rushing through a week packed with crowds and tight itineraries, a 30-day stay lets you settle into the island’s relaxed rhythm.

Mornings become sunrise walks along the water, not frantic wake-up calls. Afternoons mean discovering neighborhood cafés, hidden beaches, and the charm of Old Town at your own pace. With April’s warm breezes and lighter crowds compared to peak spring break weeks, guests can enjoy the best of the season without the frenzy.

A month-long rental gives you space to breathe, unwind, and truly experience Key West the way locals do — slowly, meaningfully, and with plenty of time to savor every moment.

With boutique historic homes, personalized service, and trusted local expertise, Historic Key West Vacation Rentals helps guests experience Key West as more than a destination — but as a place to live, explore and belong.

Start planning your April month-long retreat with us here, and discover the magic of slow spring island living.