Welcome Home Key West

Welcome Home Key West Vacation rental homes in Key West, Florida

🎄 Christmas & New Year’s Eve on DuvalWhat if you didn’t just go to the New Year’s Eve celebration in Key West… you could...
09/11/2026

🎄 Christmas & New Year’s Eve on Duval

What if you didn’t just go to the New Year’s Eve celebration in Key West… you could watch it from your own balcony? 👠✨

The Shipwreck Suite is right on Duval Street, next to the famous Red Shoe Drop at Bourbon Street Pub. On December 31, the giant red shoe descends from the balcony as the crowd counts down to midnight — and the event is broadcast to audiences around the world.

Imagine watching the celebration from your private Duval Street balcony, then stepping outside and joining the party… and who knows, you might even catch yourself on TV. 📺🥂

The Shipwreck Suite is available for Christmas and New Year’s this year.

🎄 Spend Christmas in Key West
👠 Watch the Red Shoe Drop
📍 Right on Duval Street
🌴 Private balcony
🏡 One bedroom + bonus loft
🏊 Shared pool
✨ Monthly vacation rental

Celebrate the holidays somewhere a little more memorable.

There’s something pretty special about being at Mile 0. 🌴Key West is where the road ends, the island begins, and life st...
09/10/2026

There’s something pretty special about being at Mile 0. 🌴

Key West is where the road ends, the island begins, and life starts to feel a little less rushed.

From here, there’s nowhere else to go but out on the water, down a quiet side street, or toward whatever adventure the day has in store.

Welcome to the end of the road. You might not want to leave.

We’re excited to officially offer direct booking through our website, giving you an easy way to browse our homes, check ...
09/09/2026

We’re excited to officially offer direct booking through our website, giving you an easy way to browse our homes, check availability, explore each property and book your stay directly with us.

From charming Old Town cottages to private tropical retreats, each Welcome Home property is personally managed by our local Key West team and thoughtfully prepared for every arrival.

🏝️ Browse our properties
📅 Check availability
💻 Book directly
💛 Stay with a local team who truly knows Key West

Ready to find your next island home?

Visit welcomehomekeywest.com and start planning your Key West stay.

Welcome to Key West. Welcome Home. 🌴

🌴 Poolside at the William Skelton HomeSome days in Key West are meant to be spent exploring. Others are meant to look a ...
09/08/2026

🌴 Poolside at the William Skelton Home

Some days in Key West are meant to be spent exploring. Others are meant to look a lot like this.

The private backyard pool at the William Skelton Home is surrounded by lush tropical landscaping, spacious brick patios, and plenty of room to settle in for a long, lazy afternoon.

Swim, read, sip something cold, repeat. No itinerary required. ☀️

🏡 William Skelton Home
🌴 Historic Old Town Key West
💦 Private pool
✨ Monthly stays available

There’s just something about a Key West street that makes you slow down. 🌴Colorful Conch homes, shady porches, swaying p...
09/07/2026

There’s just something about a Key West street that makes you slow down. 🌴

Colorful Conch homes, shady porches, swaying palms, and a little bit of island character around every corner.

This is the kind of neighborhood where the best way to get around is on two wheels, the houses are part of the scenery, and you never really need to be in a hurry.

Come for the sunshine. Stay for the charm.

Dockside Oasis 🌴Some vacations call for sightseeing.Others call for finding the perfect pool chair and not moving.At Doc...
09/06/2026

Dockside Oasis 🌴

Some vacations call for sightseeing.
Others call for finding the perfect pool chair and not moving.

At Dockside Oasis, you can spend the day floating in your private pool, watch boats cruise by on the canal, and let the evening roll in with palm trees and a Southwest Florida sunset.

A two bedroom home in Cape Coral, available for weekly stays.

🏊 Private pool
🌊 Canal front
🛏️ 2 bedrooms
☀️ Weekly vacation rental

09/05/2026

Casa Mamisa 🌴

Tucked away on a sweet little lane in Old Town Key West, Casa Mamisa is a cozy two bedroom, two bath home made for settling into island life.

Slow mornings at home. Bikes parked out front. A stroll to your favorite spot for dinner. And the luxury of having a comfortable place to come back to at the end of the day.

With charming spaces, a great Old Town location, and everything you need for a longer stay, Casa Mamisa is an easy place to call home for a month.

🏡 2 bedrooms | 2 baths
🌴 Old Town Key West
☀️ Monthly vacation rental

Stay awhile. Live a little more like a local.

Nauti’s Nest 🌴A charming two bedroom cottage in the heart of Old Town Key West, Nauti’s Nest is made for settling into i...
09/04/2026

Nauti’s Nest 🌴

A charming two bedroom cottage in the heart of Old Town Key West, Nauti’s Nest is made for settling into island life.

Start the morning with coffee in the bright, comfortable living space, spend the afternoon by the shared pool, and come home to a cozy place that feels like your own.

With two bedrooms, a full kitchen, and a relaxed Key West setting, it’s the perfect home base for a longer stay.

✨ 2 bedrooms
🌴 Old Town Key West
🏊 Shared pool
🏡 Monthly vacation rental

🌴 Soak up the Key West sunshine from every angle.At the William Skelton Home, there’s no shortage of places to settle in...
08/31/2026

🌴 Soak up the Key West sunshine from every angle.

At the William Skelton Home, there’s no shortage of places to settle in and enjoy the island breeze.

☀️ Upstairs front porch — morning coffee with a little more elevation and plenty of tropical views.

🌿 Downstairs front porch — a cozy spot to relax, read, or watch Old Town life go by.

🏊 Back deck — your own private retreat overlooking the backyard pool, perfect for lingering over dinner or enjoying a cocktail as the day winds down.

Three outdoor spaces. Three different ways to enjoy Key West.

Which porch would you choose? 🌴

📍 William Skelton Home | Old Town Key West
🏡 6 bedrooms | Private pool | Nightly vacation rental

🌅 Some sunsets are worth slowing down for.There’s something about a Key West sunset that makes you forget what time it i...
08/31/2026

🌅 Some sunsets are worth slowing down for.

There’s something about a Key West sunset that makes you forget what time it is. The water, the colors, the boats drifting by, and that little feeling that you’re exactly where you’re supposed to be.

Come for the island. Stay for the sunsets. 🌴

Address

Key West, FL
33040

Telephone

+15179270022

Website

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