The Shady Pineapple

In Santa Rosa Beach

Resort backyard featuring heated pool, loungers, fire pit, outdoor kitchen and dining areas!

We welcome you to

The Shady Pineapple

Escape to Shady Pineapple, a luxurious 3-story retreat just a 2-minute walk from the beach! This new home comfortably accommodates large groups and features a private heated pool, outdoor kitchen, and partial Gulf views from two balconies. Enjoy a less-crowded beach experience in a prime location. Enjoy taking the 6 person Golf Cart or ride your bicycle to local restaurants and shops! Perfect for families and friends seeking a stylish coastal getaway.

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Amenities

At The Shady Pineapple

This home has everything you will need for a comfortable stay. Guests have access to the entire home and everything the space has to offer which includes:
5 Bedrooms
Sleeps 16
5.5 Bathrooms
4 Parking Spots
Air Conditioning, Central Heating
Baking Sheet, Blender, Coffee Maker, Pots & Pans, Dishes & Utensils, Dishwasher, Freezer, Kitchen, Microwave, Oven, Refrigerator, Stove, Toaster, Wine Glasses
Linens Provided, Clothes Dryer, Extra Pillows & Blankets, Hot Water, Washing Machine
Games/Board Games, Television
Dining Table, Private Entrance
Hair Dryer, Iron & Board
Deck/Patio (uncovered)
Communal Pool
Shampoo
Free Internet

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The Details

A Bit More About This Property

Welcome to Shady Pineapple! This 3-story luxurious home is 2–3-minute walk (5 houses away) to the beach and features a heated private pool, outdoor kitchen, fire pit, 6-seater golf cart, bicycles and close proximity to Stinky’s Fish Camp, Shunk Gulley’s and Gulf Place! The beach access is just at the end of the street and has no car parking which makes it less busy and one of the best access! Enjoy partial gulf views from the second and third story balconies!

 

This home's best feature is the county owned beach access just steps away. It does offer very limited parking so it doesn't get as busy as other accesses as it is mostly visitors within walking distance!

 

DETAILS:

This gorgeous new home is set up for pure enjoyment for everyone in your family in beautiful Dune Allen Beach! Featuring 5 bedrooms, 5 ½ bathrooms and accommodations for 16, making the Shady Pineapple the dream vacation. Walk to the beach in less than 5 minutes (1 block) or walk to Gulf Place (approx. 1 mile) or stay home and enjoy the gas grill, heated private pool (can be heated for additional fee) or make a bonfire to enjoy all evening!

 

The first floor features shiplap walls with professional décor and is flooded with natural light for everyone to enjoy with an open floorplan featuring a gourmet kitchen with an oversized island featuring quartz countertop and wolf gas range, an ice maker to fill up your cooler and a spacious living room, and dining room area. The private pool has lounge chairs and a hammock surrounding it with a privacy fence for pure enjoyment. There is a pool alarm on the French doors leaving the house.

 

The second floor features suite that boasts king size bed, a balcony with a partial gulf views, private bathroom with shower. The second master bedroom features a king-size bed with a private bath that features a shower. The third bedroom features two twin-size beds with a private bathroom that features a shower and tub combo.

 

The third floor features an amazing gathering space that offers a sofa sleeper couch, a set of bunk beds and a table for games and a wet bar. All of this space is adjoining to an oversized balcony to enjoy with partial gulf view. The fifth bedroom features a king-size bed with a private bathroom that has a shower and tub combo.

 

When you're not at the beach that is one block away (less than a 5-minute walk) you can dip into the pool or relax poolside in one of the chaise lounges chairs! This luxury beach home is set up to enjoy all evening too! If you don't want to walk to Gulf Place for dinner, you can grill out in the backyard and enjoy your own private bonfire in the fire pit.

 

There is approximately 4 parking spots. There is also an attached garage that will have beach chairs, sand toys and bicycles that are available for your use. Due to damage and missing items, the contents are continually changing. We also provide beach towels!

 

HOME CONFIGURATION + SLEEPING ARRANGEMENTS:

Sleeps: 16 people

5 Bedrooms / 5.5 Baths

 

FIRST FLOOR: Sleeps 2

-Kitchen, Dining Area, and Living Room

-Primary Bedroom Suite: King Bed with Private Bath (Shower and freestanding bath)

 

SECOND FLOOR: Sleeps 8

-Bedroom Suite 2: King Bed with Private Bath with shower and balcony

-Bedroom Suite 3: King Bed with Private Bath with shower

-Bedroom 3: 2 sets of bunk beds (totaling 4 twin size beds) with a private bath with a shower/tub combo and balcony

 

THIRD FLOOR: Sleeps 6

-Bedroom Suite 4: King Bed with bath with shower/tub combo

-Bonus living room with bunk beds: 1 sofa sleeper, with wet bar and adjoining balcony with 1 set of bunk beds tucked away off the living room

 

HOME HIGHLIGHTS:

- Stunning luxury home

- High-end finishes

- Private Fire pit

- Professionally decorated

- Designed for Maximum Family Fun

- Gathering Room stocked with classic games

- Multiple Beach Accesses one block away

- Private Heated *Pool Heat is available for an additional $300 (pre-tax).

-Must sign golf cart waiver to use golf cart and rental agreement.

- Neighboring Communities – Gulf Place, Dune Allen, Blue Mountain Beach

Guests under 25 must be accompanied by an adult chaperone throughout their entire stay (we require drivers license photo). Parties and events are not allowed on the property. Pool heating is available for an additional fee, and guests must sign a pool waiver prior to staying. Security cameras are on the exterior of the home.

 

In case of hurricanes or bad weather or due to necessary repairs, certain amenities may be closed and unavailable during your stay. We cannot guarantee the availability of each amenity. We do not offer refunds for bad weather unless there is a mandatory evacuation declared by local authorities. Please see evaluate your options for travel insurance at the time of booking through the platform.

 

Guests will have exclusive and private access to the entire home and all its amenities. This includes:

The entire three-story house

Private, fenced-in yard

Heated pool and all outdoor entertainment areas

Beach essentials and bikes are provided for your enjoyment.

 

We respect your privacy and want you to feel at home. While we won't be present during your stay, we are always available via the messaging app or phone should you need any assistance or have questions.

 

For your security and ours, please be aware that exterior security cameras are located on the property. These cameras monitor the exterior of the home only and there are no cameras inside.

Why our guests

LOVE STAYING HERE

One of the best Airbnbs we’ve ever stayed at! The backyard was the perfect spot to relax and hang out, and the beach was just a short walk away. We loved having the golf cart for quick trips to grab coffee and explore the area. The house was spotless, well-stocked with thoughtful amenities, and felt so comfortable. It truly had everything we needed and more. We absolutely loved our stay—it was perfect for our trip!
Jaime O.
August 2025
Great proximity to the beach and restaurants. Loved having the golf cart to get around. Lindsay was super helpful in connecting me to get chairs set up at the beach. Some elements of the property could use some TLC
Brooke P.
July 2025
Great place close to the beach! Lindsay was helpful & the pool was nice. Would definitely stay here again!
Julie O.
May 2025
Great home for families in Santa Rosa…easy beach access and a wonderful back yard for fun and relaxation!
Kelly S.
April 2025
The house is beautiful and accommodated our large family perfectly. We thoroughly enjoyed the backyard and pool. The beach is an easy walk from the house. Our family would definitely stay here again!
Lauren E.
April 2025
Wonderful location and beautiful home! Very friendly and prompt communication as well. As far as location, it's as good as it gets! Super convenient to the beach (very walkable even with small kids). Look forward to staying here again!
Rahul A.
March 2025
Lindsay's place is beautiful and spacious. You will not want to leave it. Our family had a wonderful time and we enjoyed the backyard space! Plenty of rooms and bathrooms and supplies for the beach. Absolutely loved our stay!
Dawn S.
December 2024
Perfect size for the number in our party. We could be in the same common areas in the house, and we weren't fumbling over each other. Backyard, deck, pool and surrounding space was perfect for our use. Everything worked and functional. Lots of glassware and plates, silverware, etc. Walk to the beach and local restaurants were convenient.
Chris M.
October 2024
The perfect home for a family vacation!! Roomy main spaces and kitchen with all the gadgets needed. Spacious bedrooms and bathrooms with a perfect outdoor living space to entertain the whole family. We loved hanging outside in the backyard in the pool and playing cornhole/ping pong. We also loved that the home had bikes and beach equipment to use. Cannot harp on how incredible Lindsay was! The area was expecting a pretty gnarly storm and Lindsay was checking in to make sure we were aware of the weather and what we should expect. We hope to be back with more family next time!
Brooke M.
September 2024
Our stay was fantastic. Everyone had plenty of space in the house to spread out. It is in a fantastic location, only a short walk from the beach. Overall, we had a great time and would highly recommend this vacation spot.
Sandy A.
September 2024
Location, location! We loved how close this family friendly house was to the beach. The home was beautiful and the outdoor pool was a major bonus. The large kitchen and living room were lovely to spend quality time together. We enjoyed staying here and hope to come back again.
Rebekah R.
August 2024
We’ve been renting beach homes for over 20 years. Lindsay is among the best ever. Her home was perfect for us.
Joe P.
August 2024
Overall, we had a great stay with our group of 13. There was plenty of space for us to spread out, and the pool area was nice. The kids really enjoyed the outdoor ping pong table. The only downside during our stay was the internet; constant signal drops made watching movies or using it for remote work almost impossible. However, we would recommend and stay at the home again.
Julian M.
July 2024
We really enjoyed the house. It was the right place for the family vacation. The surrounding are great. We look forward to coming back there in the future.
Robert O.
May 2024
This is an awesome house for a large group. There are so many bedrooms and bathrooms. Our group cooked meals at home and the kitchen is a great size, the fridge is huge! The space was comfortable for all of us to eat and be entertained. The backyard is so comfortable. We loved the fire pit. location is great! It’s a quick walk down to the beach and a quick bike ride to local coffee. Easy access to sidewalks and bike paths
Monica S.
November 2023
The place was beautiful and the views and amenities were amazing. Loved being able to ride bikes to the beach and restaurants. Enjoyed the backyard watching the games and enjoyed the fire pit (have to buy your own wood). But there were no towels in bathrooms they were all in the drier and washing machine. The third floor and second floor (room to the right had blood tinged comforter/ sheets on bed and noticed some towels had dried round bugs (resembling bed bugs) on towels! There were a few stains on couches and bar stools and some scuff marks around the house. For the price of the cleaning fee it should of been a little cleaner. Other that those few things it’s definitely somewhere I would recommend and stay again.
Madison M.
November 2023
Highly recommended! The place was absolutely beautiful and spacious. The beds were very comfortable, even the bunk rooms! Perfect for a bachelorette. The beach is 5 min walk away. We couldn’t recommend this place enough!
Vy N.
October 2023
We had a fabulous stay at this place. So many activities for the beach and otherwise, we had the best time!
Glenn H.
September 2023
This house has everything you need- it’s location to the beach is perfect! The pool and backyard so relaxing and ideal for kids and adults! Inside is spacious with plenty of room for everyone and the amenities are top notch ! The location is close to shops and restaurants but nicely a mile down the road so you don’t have all the people and traffic! Ideal vacation spot!
Nicole C.
April 2023