Golfing on-site, a water park and laundry facilities are just a few of the amenities provided at Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama. Enjoy on-site activities, such as snorkelling and motor boating. Stay connected with free in-room WiFi.
Reviews
9.89.8 out of 10
Exceptional
Entire home
5 bedrooms6 bathrooms2495 sq ft
Popular amenities
Ocean view
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama
Book your summer vacation now! Book with confidence knowing the best available discount has been applied for your stay - no codes necessary.
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. Boat trailers cannot be parked at the house. To arrange for trailer parking we suggest you contact Perdido Key Rentals 850-450-5401-Angela Bateman
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. Bulkhead with lounging area on the sugar white sand.
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.
Property amenities
Beach
Beach nearby
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Dishwasher
Hob
Ice maker
Kitchen island
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
5 bedrooms
Bedsheets provided
Bathroom
5.5 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Towels provided
Living spaces
Dining table
Living room
Separate dining area
Entertainment
Smart TV
Outdoor areas
Balcony
Barbecue grill
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Limited housekeeping
Location highlights
In the city centre
Near a health/beauty spa
Near a hospital
Near a zoo
Near an outlet shopping centre
Near the bay
Near the marina
Near the ocean
On the waterfront
Things to do
Birdwatching
Golf
Motor boating
Optional golf privileges
Snorkelling
Surfing/bodyboarding
Water park
Wildlife walks
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Jet skiing nearby
Kayaking nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Swimming nearby
Theme park nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Located in Pensacola, this holiday home is in the city centre and on the waterfront. The Wharf and Tanger Outlet Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Gulf State Park and Perdido Key Beach. The Park at OWA and Orange Beach Indian and Sea Museum are also worth visiting. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails. Visit our Perdido Key travel guide
Is Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama pet-friendly?
No, pets are not allowed at this property.
How much is parking at Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama?
On-site parking is available at the property.
What time is check-in at Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama?
Check-in begins at 4:00 PM.
What time is check-out at Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama?
Checkout is at 10:00 AM.
Where is Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama located?
Located in the heart of Pensacola, this holiday home is within a 5-minute walk of Ono Island and Perdido Key Beach. Orange Beach Beaches and Gulf State Park are also within 3 miles (5 km).
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Waterfront Beach| Complimentary Private Boat Slip| Community Pool & Pickle Ball| Steps to Flora-Bama Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
I almost overlooked this property because I didn't catch that there were trundles in two of the rooms the first time I looked at it, but it was a beautiful property with all the amenities and space we needed. We saw lots of wildlife, including two dolphins, and thoroughly enjoyed our stay. Highly recommend.
Sarah B.
Stayed 4 nights in May 2025
From a partner site
10/10 Excellent
Mason R.
1 Apr 2025
Above and Beyond
This home was perfect and was more than I expected. The house was extremely clean and beautiful with a fantastic view of the canal. We sat outside on the deck for hours. It is hard to find such a quiet spot that was so close to great restaurants and a gorgeous beach. We easily fit our large group and the main level was perfect to get everyone together, cook a meal, and watch a movie.
We will definitely stay here again and next time for longer!
Mason R.
From a partner site
10/10 Excellent
Hannah A.
1 Apr 2025
I recently had the pleasure of staying at this incredible home in Florida, and it exceeded all expectations! I was struck by how spacious and impeccably clean everything was. The decor is beautiful - thoughtfully designed with a perfect blend of coastal charm and modern elegance. The furniture/bedrooms were no exception - the mattresses were so comfortable! One of my favorite features is that every bedroom has its own bathroom, adding an extra level of convenience and privacy for everyone in the group.
The location couldn't be better - half a mile from the Flora-Bama, Yacht Club, and Ole River making it easy to enjoy great live music, delicious food, and fun on the water. And, of course, Waffle House for those late night cravings! :)
My favorite part of this stay was watching dolphins swim by on Ole River while I was reading on the porch. It was amazing!
I can't recommend this home enough! If you're looking for a gorgeous, well-appointed place to stay with unbeatable views and an ideal location, you've found it! I will definitely be back!
Hannah A.
From a partner site
10/10 Excellent
Robert w.
3 Apr 2025
A Wonderful Stay
We love the Perdido Key area. It is beautiful and relaxing. The people are friendly, the beaches are the best, and you can't beat the seafood!
The house is near one of our favorite hangouts, Flora-bama! It is two stories, tastefully decorated, and so spacious. Everything is modern, but comfortable and inviting. There were six of us, with five bedrooms, we were able to spread out and enjoy this lavish retreat. The bedrooms are laid out well and the beds were very comfortable. There was enough space to sleep at least 8 more comfortably.
The kitchen is beautiful with stainless appliances. We loved the wet bar with the ice maker!
We enjoyed the view off the back deck. The channel is so calming and we all believe we saw an eagle!
There is a small beach area right behind the house, but it was too cold to enjoy the water right now. There is a boat slip, but we don't own a boat.
We are very pleased with our choice and will definitely be back!!
Thank You
We stayed at Win Win for our annual friends get away and the accommodations were perfect. The house is well outfitted with everything your need for an enjoyable stay. Plenty of room, beautiful views of the bay, a very nice boat dock and so much more. The beds were so comfortable and everything was clean! We have added this to our top 3 places to stay as it fit our needs perfectly. The only thing that kept it from being the absolute best place we’ve ever stayed was the pool- small, really just a place to take a quick dip. BUT we came here for the beach and boating, the pool was a bonus! Our booking agent Mrs Patty was so nice and accommodating, we will be booking with her again soon! Thank you for a great stay!
Alan N.
From a partner site
10/10 Excellent
Russell A.
9 Jun 2025
Family Vacation
Perfect place for our crew. The house was so nice and clean. The host was amazing. Having access to dock our boat was icing on the cake. Will stay here again for sure.