- Home

Visual Image

Discover Key West

VACATION HOMES BY THE WATER
Prev Next
Start Your Escape

Vacation Rentals

Bedrooms
Length of Stay
Coastal Comfort 4 Bedroom Key West Rental
Coastal Comfort 4 Bedroom Key West Rental
Key Cove

Coastal Comfort

  1. 4bd
  2. 3ba
  3. Sleeps 10
  4. Pool
30 nights min stay
VIEW rental
Key West Vacation Home with Waterfront Views
Key West Vacation Home with Waterfront Views
Key Cove

Nautical Wheeler

  1. 4bd
  2. 3ba
  3. Sleeps 8
  4. Pool
29-30 nights min stay
VIEW rental
Havana Daydream Key West Vacation Home
Havana Daydream Key West Vacation Home
Key Cove

Havana Daydream

  1. 4bd
  2. 3ba
  3. Sleeps 9
  4. Pool
29-30 nights min stay
VIEW rental
Southern Comfort Key West Vacation Rental
Southern Comfort Key West Vacation Rental
Key Cove

Southern Comfort

  1. 4bd
  2. 3ba
  3. Sleeps 10
  4. Pool
23 nights min stay
VIEW rental
Key West Vacation Home with Waterfront Views
Key West Vacation Home with Waterfront Views
Key Cove

Banana Breeze

  1. 4bd
  2. 3ba
  3. Sleeps 10
  4. Pool
29-30 nights min stay
VIEW rental
Paris Mango 4 Bedroom Key West Vacation Home
Paris Mango 4 Bedroom Key West Vacation Home
Key Cove

Paris Mango

  1. 4bd
  2. 4ba
  3. Sleeps 9
  4. Pool
29-29 nights min stay
VIEW rental
Key West Vacation Home with Boat Dock
Key West Vacation Home with Boat Dock
OLD TOWN

Captain’s Daughter

  1. 4bd
  2. 3ba
  3. Sleeps 12
  4. Pool
30 nights min stay
VIEW rental
Seafarer's Refuge Key West Vacation Home
Seafarer's Refuge Key West Vacation Home
OLD TOWN

Seafarer’s Refuge

  1. 4bd
  2. 3ba
  3. Sleeps 12
  4. Pool
4-8 nights min stay
VIEW rental
Key West Vacation Rental with Waterfront Views
Key West Vacation Rental with Waterfront Views
OLD TOWN

Eisenhower Retreat

  1. 4bd
  2. 3ba
  3. Sleeps 12
  4. Pool
4-9 nights min stay
VIEW rental
5 Bedroom Bayview Key West Vacation Home
5 Bedroom Bayview Key West Vacation Home
OLD Town

Bayview Retreat

  1. 3bd
  2. 4ba
  3. Sleeps 2
  4. Pool
4-5 nights min stay
VIEW rental

Our Difference

Stunning Views Icon

Stunning Views

Key West is unlike any place you’ll ever see. Why not see it the right way? Awake to dazzling daybreaks and wind down with sensational sunsets in your own private paradise. Many of our vacation rentals offer sweeping balconies and airy floor plans so you can enjoy the island view.

Docks Included Icon

Docks Included

Living like a local doesn’t just happen on land. That’s why most of our Key West vacation homes come with a private boat slip. So you can accent your escape with fishing adventures, snorkeling expeditions or deep dives for dinner. Or just dock your boat and soak in the sunset.

Easy Breezy Icon

Easy Breezy

Key West is a unique and different place. Shoes and schedules are shunned here. Which is why we accommodate different lengths of stays. From weekend getaways to month-long immersions, our flexibility is practically unheard of in this part of paradise. Let us know exactly what you want, and we’ll make it happen.

White Glove Service Icon

White Glove Service

Come unwind with us, and discover an immersive and all-inclusive experience that’s every bit as remarkable as your location. Want a fresh meal delivered to your door? Need your laundry cleaned? Curious about local hangouts? Our “white glove” concierge service gives you whatever you want. Whenever you need it.

Renew & Refresh Icon

Renew & Refresh

There’s something special about your own private oasis. Most of our Key West vacation rentals feature an expansive pool. So you can wash off from your ocean adventure. Or just chill by the water with a fresh drink. Whatever your style, we’ll provide you with plenty of beach towels and sun rays.

Perfect Balance Icon

Perfect Balance

Our spacious homes are both modern and charming. Enjoy full kitchens, expansive balconies and wide-open rooms. Enveloped in lush natural surroundings. From bachelorette parties to weddings, from family vacations to corporate retreats, we offer something for everyone. All accented and elevated by a higher level of personal service.

Area Guide

VIEW ALL

If it involves fun in the sun, pro tips on how to mix in with the locals, a recommendation for some tasty neighborhood eats or anything that would make your stay with us the very best travel experience you’ve ever had, you can find it here!

IMPORTANT: You may have seen ads on Airbnb or Craigslist that appear to be about our properties or seem to have been placed by us. Please note that Key West Vacation Homes does NOT advertise on either Airbnb or Craigslist – and your response to any fraudulent “ad” for a Key West Vacation Homes property on either of these sites is NEVER received by us. These are fake ads run by scammers who have NO intention of honoring your reservation. All of us here at Key West Vacation Homes take pride in the security of all our guests. To further protect your valuable personal and financial information and ensure you are renting and communicating with Key West Vacation Homes, contact us directly by phone, email, or via our HomeAway listings.

Please note: 30 night minimum stay required on some homes due to a City of Key West ordinance and not negotiable.