Featured Spend April your way: A curated guide to slow travel, culture & comfort in Key West April in Key West is a reminder of how refreshing slow travel can be. The air is warm and soft, the crowds are light, and the island’s cultural calendar is full of creativity and history. For travelers looking to spend a full month reconnecting, (read) Published on Jan 11, 2026
Featured New to our vacation rental portfolio: Flamingo Cottage and Gardenia Cottage There's something magical about traveling with loved ones - the shared laughter, the unplanned adventures, the long evenings that turn into lifelong memories. But even between family or friends, a little downtime and privacy can work wonders. Introducing... (read) Published on Nov 04, 2025
Featured Oceanfront Views + Island Sunshine: Newly Available for Feb–March 2026 A rare cancellation has just opened the calendar in February and March 2026 at Azur Palm — one of our most sought-after waterfront monthly rentals in Key West ( with a perfect 5.0 guest rating ). If you’ve dreamed of escaping winter and trading (read) Published on Oct 21, 2025
Featured Key West gift guide: Give gifts of sand and sunshine this December When it comes to holiday giving, the best presents aren’t always wrapped in paper and bows. Sometimes, the most meaningful gift is time spent together, away from the cold and stress of the season. This year, why not surprise your loved ones with (read) Published on Oct 12, 2025
Featured December in Key West: Book ahead for a holiday in paradise The island transforms in December with a festive cheer that’s equal parts tropical and traditional. Families will find an endless lineup of events and activities, all enjoyed in flip-flops and sundresses, rather than snow boots and parkas. Here (read) Published on Oct 05, 2025
Featured Discovering a quiet island treasure in the Key West Public Library When people imagine Key West, they often picture pastel cottages, sun-drenched porches, and the hum of live music drifting through the streets. But just off the beaten path, among swaying palms and historic homes, there’s another kind of island (read) Published on Sep 28, 2025
Featured From the heart of Texas to the soul of Key West: Why the Conch Republic calls to Lone Star traveler If everything’s bigger in Texas, then everything is bolder in Key West — from its colorful, history-rich homes to its legendary fishing tales that rival anything reeled in on the Gulf. For Texans with a taste for character, charm, and (read) Published on Sep 21, 2025
Featured Indulge your senses at Fantasy Fest! Find your perfect stay with Historic Key West Vacation Rentals Every October, Key West comes alive with color, music and imagination for one of the island’s biggest events of the year: Fantasy Fest. This 10-day extravaganza (Oct. 17-26) draws visitors from around the world for a whirlwind of themed parties, (read) Published on Sep 05, 2025
Featured Settle In. Slow Down. Live The Story. At Historic Key West Vacation Rentals, we believe travel should be more than a getaway. It should be a connection — to a place, a past, and a way of life that invites you to stay a little longer, breathe a little deeper, and feel a little more like... (read) Published on Aug 01, 2025