Looking for a great deal? Discounts are automatically applied based on your length of stay—whether it’s 5 nights, 7 nights, 28 nights, or more! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price!
Welcome to Win-Win at Yacht Harbor
A Luxurious 5-Bedroom Waterfront Retreat with Private Boat Slip included
Escape to Win-Win at Yacht Harbor, a professionally decorated 5 bedroom, 5.5 bathroom vacation home designed to accommodate up to 16 guests. This spacious and elegant retreat blends comfort, entertainment, and relaxation. It’s perfect for your next beach getaway.
Private Boat Slip Just Steps Away
Enjoy direct water access with a private boat slip right outside your back door. The boat slip is included in your rental. If you’re planning to use the boat slip please message the host as additional paperwork is required.
Elevator Access available for Guests with Physical Handicaps
Please contact the host to discuss qualifications and additional paperwork. In addition, a refundable security deposit is required to use the elevator.
World-Famous Flora-Bama just down the street
Just a short walk to the Flora-Bama Beach Bar, where you can enjoy live music every day of the year
An Unbeatable Community Experience
Located in the new Yacht Harbor community, guests enjoy exclusive access to:
• Heated Community Pool
• Pickleball court (bring your own equipment)
• Fishing piers
Breathtaking Water Views
Take in stunning views of Ole River and surrounding waterways from 4 private outdoor spaces:
• Main Floor Balcony - Dine alfresco or unwind with a sunset view.
• Top Floor Primary Suite Balcony - Enjoy your morning coffee with serene water views
• Ground Floor Patio - Grill your fresh catch and relax by the water.
• Ole River Beach - Just outside your back patio for easy shoreline access
Spacious & Inviting Interior
Step inside through your private entrance to a beautifully designed, open concept living space featuring:
• Fully Equipped Kitchen with stainless steel appliances, double oven, microwave, 12 cup coffee maker with integrated single serve Keurig, and ample counter space and cookware.
• Wet Bar with Mini-Fridge & Ice Maker - perfect for entertaining
• Smart TV & Comfortable Seating Area with balcony access.
• Convenient Half Bath on the main level.
Comfortable Sleeping Arrangements
After a day of beach adventures and excursions, retreat to one of five stylish and well-appointed bedrooms:
On the Upper Level…
• Primary Suite - King bed, Smart TV, private balcony, en suite with 2 individual vanities, soaking tub, and massive walk-in shower with 2 shower heads and a built-in bench
• Guest Bedroom 2 - Queen bed, Smart TV, en suite with spacious walk-in shower and partial view of the Gulf
• Guest Bedroom 3 - Double-over-double bunk beds AND a double pull-out trundle, Smart TV, and en suite with tub/shower combo - great for families or kids
• Guest Bedroom 4 - Queen bed, Smart TV, en suite with spacious walk-in shower
• Laundry Room with Full-Size Washer & Dryer conveniently located near bedrooms
On the Main Level…
• Another Primary Suite - King bed, two XL twin pull-out beds, Smart TV, en suite with double vanity and spacious walk-in shower
• Traveling with little ones? We have a pack n play and highchair for your convenience
Parking & Nearby Attractions
• 2 parking spots inside the Garage for shaded parking
• Additional room for 4 vehicles in the driveway
• PLEASE NOTE: If bringing a boat you must store the trailer off site. You may contact Perdido Key Boat Rentals for trailer storage and fees (850) 450-5401
Just Minutes from Perdido Key’s White Sand Beaches and Close To…
• Johnson Beach (Gulf Islands National Seashore)
• Kayaking, paddle boarding, and parasailing
• Publix & Winn Dixie grocery stores within a short drive
• Orange Beach, Gulf Shores & Downtown Pensacola within easy reach
Exclusive Free Fun with our Xplorie Benefits
Enjoy complimentary daily admission to top local attractions, including…
• Golf at Lost Key & Soldiers Creek Country Clubs
• Tropical Falls Theme Park at OWA
• Dolphin, Sunset & Nature Cruises
Note: Xplorie is valid for stays under 28 days. Details provided upon booking
During Your Stay, Enjoy!
• Community pool - We supply 4 beach/pool chairs for your convenience
• Pickleball court – be sure to pack your equipment
• Fishing off the community dock – bring your gear
• Designated boat dock access (contact host for details)
• Elevator access for qualified quests (contact host for details)
• Smart TVs in every room
• Washer & dryer
• Free Wi-Fi via Starlink Satellite
• BBQ grill on back patio
Nearby Attractions…
• Gulf Islands National Seashore (Johnson Beach)
• Naval Aviation Museum
• Parasailing & Water Activities
• Big Lagoon State Park
• Lost Key Golf Club
• Tarklin Bayou Preserve State Park
• Pensacola Lighthouse & Maritime Museum
• Perdido Key Public Beach Access
…And So Much More!
Book Your Stay with us at Win-Win at Yacht Harbor!
We strive to create a winning vacation experience for your entire group - families, friends, and beach lovers alike!
Enjoy nature, find an attraction, do some shopping, enjoy dining and nightlife, become part of the island experience in the Perdido Key area! Gulf Islands National Seashore was named “Best Beach in Florida” in 2015 by USA Today. Go kayaking, charter a boat, watch the dolphins, walk a trail, spend time on the beach, eat some fresh seafood. There is so much to do on Perdido Key!
With an average temperature of 75 degrees and 343 days of sunshine, the key is a long-hidden retreat that blends together both year-round outdoor activities and a laid-back island lifestyle.
** House Rules: Minimum age to rent is 25. Reservations for teenagers or young single groups will not be honored without an accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. Be respectful of the property & contents - it is someone's home. Respect your neighbors. No parties, events or smoking of any kind. Evidence of smoking will result in additional cleaning fees.
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Xplorie benefits apply to stays LESS THAN 28 days.
