The Meadows Rentals USA Florida Key West The Meadows

Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool | House in Key West

New |   4 Bedrooms  4 Bathrooms  10 Guests
New Listing
The Meadows House | Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool

4 Bedroom House in The Meadows, Key West

Island Dreaming – Your Luxury Key West Getaway
Welcome to Paradise
Discover the ultimate island retreat at Island Dreaming, a spectacular Key West vacation home nestled between the charm of Old Town and the tranquility of the Meadows District. Whether you're traveling with family or friends, this private oasis blends upscale amenities with the laid-back lifestyle of the Keys.
Property Highlights
Location: Quiet yet central – walk to downtown, yet enjoy serene privacy
Bedrooms: 4 spacious bedrooms including two primary suites
Bathrooms: 3.5 modern bathrooms
Parking: Off-street parking for 1 vehicle
Size: Comfortably sleeps 8+ guests
Outdoor Oasis
Private Saltwater Pool: 12’ x 18’, heated (by request), custom-tiled with waterfall & in-pool loungers
Outdoor Kitchen: BBQ grill, sink, and ice-maker – perfect for entertaining
Multiple Outdoor Living Spaces:
Expansive front porch for morning coffee
Back deck for cocktails under the stars
Shaded & sunny lounging areas
Lush Landscaping: Tropical flora, paver walkways, irrigation, and outdoor lighting
Interior Features
Seamless Indoor-Outdoor Living: 9-ft ceilings & 16-ft glass doors connect the living area to the poolside deck
Gourmet Kitchen: Fully equipped for all your culinary needs
Wine Lovers’ Dream: 600-bottle, walk-in, climate-controlled wine room
Two Primary Suites:
First-floor suite with private bath
Second-floor suite with vaulted pine ceiling & private balcony
Bright Living Room: Natural light and pool views with wall-to-wall glass doors
Additional Amenities
Whole-house water filtration system
Custom-designed staircase
Pool heat available (fee applies; must be requested in advance)
High-speed WiFi & smart TVs
Washer & dryer
Perfect Location
Located in a diverse, upbeat neighborhood, Island Dreaming puts you close to:
Duval Street nightlife
Local restaurants & bars
Art galleries, shops, and attractions
Beaches & marinas
Ideal For
Families
Groups of friends
Extended stays
Guests seeking a luxury, peaceful vacation with easy access to the action
Additional fees may be added after booking:
Pool heating fee of $300 per month for the months of November-March(optional)
Reservations of more than a month require a mid stay cleaning fee
*** Please note the from Nov - April rentals are required to start on the 1st of the calendar month, Any month that includes February has to be either Jan/Feb or Feb/March. We are unable to split the month. The house is available to rent from November 1st 2025.
Book Your Stay Today and Start Living the Island Dream!

Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool is located in The Meadows. Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool provides accommodation, featuring Fireplace/Heating, Guest Services, Child Friendly, among other amenities. This House features Fireplace/Heating, Guest Services, Child Friendly, to make your stay a comfortable one.

Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool has 4 Bedrooms , 4 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the The Meadows has interesting places to visit. If you want to learn more about the House in The Meadows, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY
 
Key West, 33040, United States

Amenities

Air Conditioner
Parking
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Shower
  • Towels provided
  • Hair dryer
Bedroom
  • Bed sheets provided
  • Dining table
  • Living room
Kitchen
  • Oven
  • Microwave
  • Cookware/dishes/utensils
  • Coffee/tea maker
  • Ice maker
  • Dishwasher
  • Kitchen island
  • Refrigerator
  • Stovetop
Laundry
  • Washing machine and dryer
  • Near laundromat
Parking
  • Onsite parking
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Tennis on site
  • Golf nearby
  • Marina nearby
  • Fitness facilities nearby
  • Ecotours nearby
  • Cycling nearby
  • Water skiing nearby
  • Bicycle on site
  • Jet skiing nearby
  • Fishing nearby
  • Water tubing nearby
  • Birdwatching nearby
  • Golfing on site
Entertainment
  • Smart TV with cable/satellite service
General
  • Unit size: 2500 sq ft (232 sq m)
  • English
  • Spanish
  • Near the sea
  • In the city center
  • Near a hospital
  • Desk
  • Computer monitor
  • Desk chair
Guest Services
  • Iron/ironing board
  • Housekeeping (on request)
Internet
  • Free WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices)
Outdoors
  • Balcony
Security/Safety
  • Fire extinguisher
  • Deadbolt lock
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • First aid kit
Spa
  • Private pool

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted
Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

FAQ's

Is this The Meadows house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the The Meadows house have a swimming pool?

Yes, this The Meadows house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in The Meadows house?

Best-rates for the The Meadows house starts from $605 per night with includes Laundry, Air Conditioner, TV, Ocean View, Fireplace/Heating, Guest Services, Child Friendly, Parking, Pool, Oceanfront, Sports/Activities, Security/Safety, Wellness Facilities, Internet, Kitchen, View, Private Pool, Balcony/Terrace, Bedding/Linens with all other facilities. RBO matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is The Meadows house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the The Meadows house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the The Meadows house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the The Meadows house?

Based on the information reported by the owner or manager, the The Meadows house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for The Meadows house?

Based on the information reported by the owner or manager, details for the cancellation policy for the The Meadows house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

People Also Ask

Check House Availability
Nightly rates from:
US $605
Price Details
You will be redirected to  
Hot Deal - It has been viewed 6 times today
Not the right fit? Check out our other properties in The Meadows
See More

Why is Rent By Owner The Meadows Your Choice for Vacation Rentals

Find your dream vacation rental on Rent By Owner, where adventure meets comfort in every corner. RentByOwner features a broad mix of accommodations, from charming country cottages and chic city apartments to tranquil beachfront villas and cozy mountain cabins. Whether you're yearning for a delightful bungalow by the bay, a grand estate over the dock, or a snug lodge in a quaint village, we've got the perfect spot for you.

Prepare to unleash your inner explorer with our unique lodgings, including floating houses, whimsical treehouses, and picturesque farmhouses, or stick to the classics with duplexes, flats, and guesthouses. Choose the simplicity of a studio or the luxury of a suite. For outdoor enthusiasts, we offer tents in hidden campsites, RVs, mountain cabins, boat rentals, chalets in snowy havens, and caravans in lush gardens. Rent By Owner truly has something for everyone.

Every holiday rental, from a humble hut to a lavish resort, guarantees a memorable stay with cozy beds, functional kitchens, and welcoming living areas. Ideal for families, couples, or solo adventurers, our rentals are more than just a place to sleep—they're your home away from home. Book your next vacation with us and embark on a unique retreat crafted for relaxation and adventure. We also offer annexes for added privacy, designer lofts for a modern touch, and motels for quick stays. Explore beachside bungalows, countryside ranches, and urban condos. Find your perfect getaway, whether it’s a quiet den in the forest or a bustling inn by the island. At RentByOwner, our properties include everything from houseboats and barns to court-style quarters and garden retreats.

To make your booking experience even more convenient, we help you compare prices and inventory so you can find and book your vacation rental on popular platforms like Airbnb, Expedia, Vrbo (previously HomeAway), TripAdvisor (FlipKey), Booking.com, and HomeToGo. We work with these trusted sites to offer you a seamless booking process, ensuring that your perfect vacation rental is just a few clicks away.

Popular Vacation Rental Destinations

Recently Discovered on Rent By Owner