Entire home

20% off Spring Break! Stay 5 Nights Until April 30th at Save with iTrip Perdido Key

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Main level balcony, where you can enjoy sunsets and plenty of boat activity
Professional decorated interiors shine
Comfortable lounging for the whole group
Everyone can relax in this spacious living area
Perfect spot for the family move night

Reviews

10 out of 10
Exceptional
5 bedrooms5+ bathroomsSleeps 16231.8 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Kitchen
  • Barbecue grill
  • Outdoor space

Explore the area

Map
Pensacola, FL
  • Big Lagoon State Park
    ‪5 min drive‬
  • Pensacola Naval Air Station
    ‪7 min drive‬
  • Perdido Key Beach
    ‪16 min drive‬
  • Naval Outlying Field Barin (NHX)
    ‪38 min drive‬

Rooms & beds

5 bedrooms (sleeps 16)

Guest Bedroom

2 Single Beds and 1 King Bed

Guest Bedroom

1 Queen Bed

Guest Bedroom

1 Queen Bed

Guest Bedroom

1 Double Bed and 1 Single Bunk Bed

Primary Bedroom

1 King Bed

5 bathrooms, 1 half bathroom

Guest Bathroom

Toilet · Shower only

Guest Bathroom

Toilet · Shower only

Guest Bathroom

Toilet · Shower only

Guest Bathroom

Toilet · Shower only

Powder Room

Toilet

Primary Bathroom

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony

About this property

20% off Spring Break! Stay 5 Nights Until April 30th at Save with iTrip Perdido Key

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
Escape to **Win Win at Yacht Harbor**, a professionally decorated **five-bedroom, 5.5-bathroom vacation home** designed to accommodate up to **16 guests**. This spacious and elegant retreat blends comfort, entertainment, and relaxation—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. **Message the host for boat slip rates and to reserve the slip for your stay.**

**World-Famous Flora-Bama just down the street!**
You're just a short walk from **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:
**Pickleball courts** (bring your own equipment)
**Fishing piers**
**Coming Soon: Heated Community Pool - message host for status of completion - currently estimated 4/30/25 completion**

## **Breathtaking Water Views**
Take in stunning views of **Ole River and surrounding waterways** from three private outdoor spaces:
**Main Floor Balcony:** Dine alfresco or unwind with a sunset view.
**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:
**Smart TV & Comfortable Seating Area** with balcony access.
**Fully Equipped Kitchen** with stainless steel appliances, ample counter space, and cookware.
**Wet Bar with Mini-Fridge & Ice Maker**—perfect for entertaining!
**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:

### **Upper Level:**
**Primary Suite:** King bed, Smart TV, private balcony, en suite with **walk-in shower, soaking tub, and dual vanities**.
**Guest Bedroom 2:**Queen bed, Smart TV, en suite with **walk-in shower**.
**Guest Bedroom 3:**Double-over-double bunk beds **with 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 **shower/tub combo**.

**Laundry Room with Full-Size Washer & Dryer** conveniently located on the upper level.
**Traveling with little ones? We have a pack n play and high chair!

### **Main Level:**
**Guest Bedroom 5:** King bed + **two XL twin pull-out beds**, Smart TV, en suite with **double vanity and walk-in shower**.

## **Parking & Nearby Attractions**
**Two-Car Garage + Driveway Parking for Four Vehicles**.
**Just Minutes from Perdido Key’s White Sand Beaches**!
Close to:
-**Johnson Beach (Gulf Islands National Seashore)**
- **Kayaking, paddleboarding, and parasailing** nearby
- **Publix & Winn Dixie** grocery stores within a short drive
- **Orange Beach, Gulf Shores & Downtown Pensacola** within easy reach

## **Exclusive Free Fun with Xplorie!**
Enjoy **complimentary daily admission** to top local attractions, including:
**Golf at Lost Key, Soldiers Creek & Glenlakes Golf Clubs**
**Tropical Falls Theme Park at OWA** **Dolphin, Sunset & Nature Cruises**
*(Valid for stays under 28 days. Details provided upon booking.)*

## **During Your Stay, Enjoy:**
**Community pool** (coming soon!)
**Pickleball courts**
**Fishing off the community dock**
**Designated boat dock access** (optional, additional fee)
**Smart TVs in every room**
**Washer & dryer**
**Free WiFi**
**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**

## **Book Your Stay at Win Win at Yacht Harbor!**
We strive to create a **win-win experience for your entire group**—families, friends, and beach lovers alike!
**Reserve your perfect getaway today!**
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 manager

Patty & Dan Cummings
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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

About the area

Perdido Key

Located in Chandelle First, a neighbourhood in Pensacola, this holiday home is near theme parks and on the waterfront. Fort Pickens is a notable landmark, and the area's natural beauty can be seen at Gulf State Park and Perdido Key Beach. Blue Wahoos Ballpark and Pensacola Children's Museum are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Pensacola, FL

What's nearby

  • Big Lagoon State Park - 5 min drive - 3.8 km
  • Perdido Bay Golf Club - 7 min drive - 5.2 km
  • Pensacola Naval Air Station - 7 min drive - 6.0 km
  • Perdido Key Beach - 16 min drive - 10.2 km
  • Pensacola Beach Beaches - 67 min drive - 52.0 km

Getting around

  • Pensacola Station - 29 min drive
  • Pensacola, FL (PNS-Pensacola Intl.) - 41 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Hub Stacey's at the Point - ‬7 min drive
  • ‪Sonic Drive-In - ‬8 min drive
  • ‪The Original Point Restaurant - ‬7 min drive
  • ‪The Jellyfish - Seafood Restaurant and Bar - ‬7 min drive

Frequently asked questions

Is 20% off Spring Break! Stay 5 Nights Until April 30th at Save with iTrip Perdido Key pet-friendly?

No, pets are not allowed at this property.

What time is check-in at 20% off Spring Break! Stay 5 Nights Until April 30th at Save with iTrip Perdido Key?

Check-in begins at 4:00 PM.

What time is check-out at 20% off Spring Break! Stay 5 Nights Until April 30th at Save with iTrip Perdido Key?

Checkout is at 10:00 AM.

Where is 20% off Spring Break! Stay 5 Nights Until April 30th at Save with iTrip Perdido Key located?

Located in Chandelle First, this holiday home is within 3 miles (5 km) of Big Lagoon State Park, Ascension Sacred Heart Health Center at Perdido and Shops at Perdido Key. Garcon Bayou Nature Park is 2.9 mi (4.6 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Robert w.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Mason R.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Hannah A.

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!

About the host

Hosted by Patty & Dan Cummings

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests