The Sailing Dream
A Destin, Florida Beach Vacation Rental. Your trip awaits.
About the sailing dream
Your Relaxing Beach Getaway in Destin, FloridaThe Sailing Dream is a large vacation rental perfect for families and groups of up to 16 peopleRelax at the steps-away, year-round pool and hot tubExplore the beach, restaurants, and Destin Harbor BoardwalkAdventure to Crab Island, Henderson Beach State Park, or 30ARent bikes, boats, and a house on the beach during your vacationWhether you’re here for sun, sand, or activities, The Sailing Dream puts you in the heart of everything Destin has to offer
What you can expect
Property Highlights
⛵ Walk to the beach
⛵ Sleeps 16
⛵ Year-round pool and hot tub
⛵ In-Unit Laundry (washer and dryer)
⛵ Two Balconies
⛵ Two fully renovated showers
⛵ Parking for 3 vehicles
⛵ Fully equipped kitchen and grill
⛵ High Chair
⛵ Responsive Owners
⛵ An AirBnB "Guest Favorite"
⛵ Longer stays welcome--message for discounts
⛵ New for 2026: Select furniture updates
Comfort Awaits
Gallery
Images from our 6-bedroom, 3.5-bathroom, 16-person property
Parking Options
The Sailing Dream has a strict, 3 vehicle limit that is controlled by the City of Destin. The neighborhood has very limited overflow parking that is typically full during peak season, so we recommend coordinating with an off-site parking provider in advance of your arrival if you need additional parking.While we’re happy to share suggestions, The Sailing Dream cannot guarantee availability, price, or security of off-site parking options.
The Destin-Ft. Walton Beach Airport, is just a 30 minute drive from The Sailing Dream and only charges $8.50 a day.
Geronimo RV Park offers vehicle storage starting at $25/night. They can be reached at (850) 424-6801.
Destin Tow Brothers has secure lots. Give them a call at (850) 273-8490 for rates and availability.
iStorage offers weekly storage options at two locations near The Sailing Dream. Call the Airport Road location at (850) 821-3822 or the Gulfstarr Dr location at (850) 427-0526 for rates and availability.
Longer Stays
Looking for a comfortable extended stay in Destin, Florida? The Sailing Dream is the perfect home away from home for travel nurses, military personnel, remote workers, and long-term vacationers seeking a fully furnished rental near the Gulf Coast.We offer fully furnished, monthly rental or mid-term housing in Destin. Whether you're TDY with the military or on a seasonal work contract, you’ll enjoy the comfort of a private coastal home instead of a cramped hotel.Destin and the surrounding Emerald Coast have several medical facilities that bring travel nurses and healthcare professionals to the area year-round. We are located near Ascension Sacred Heart Emerald Coast and medical centers and facilities associated with the HCA Fort Walton-Destin Hospital network. Our Airbnb is conveniently located near the following cities: Crestview, Destin, Fort Walton Beach, Freeport, Grayton Beach, Mary Esther, Miramar Beach, Navarre, Niceville, Santa Rosa Beach, Seaside, Shalimar, Valparaiso, among other areas.The Sailing Dream is also a great option for military members and families on PCS orders, TDY assignments, or training rotations along Florida’s Emerald Coast. We are conveniently located near Eglin Air Force Base, Duke Field and Hurlburt Field, making the property a comfortable option for those seeking military temporary housing in Destin. Check out our listing on TDYHeroWorking from home? Thinking about moving to the area and want to check it out first? Let us know.Unlike standard hotel rooms, our coastal retreat offers the space and amenities that make long stays enjoyable, including access to a resort-style pool and hot tub open year-round. After work, you can relax by the water, explore nearby beaches, or enjoy Destin’s incredible dining and outdoor activities.Please send us a message via our AirBnB link and we will curate an offer for you for longer stays.
Where you can find us
Location
We are located in the lovely Villages at Crystal Beach neighborhood.Our property is a 12-minute walk to the beach.Our front door is directly across from the pool and hot tub.
Why visit Destin and the emerald coast
things to do
🐬 Spend the day on the famous Crab Island sandbar
🐬 Walk the trails and beaches at Henderson Beach State Park
🐬 Watch sunset boats along the Destin Harbor Boardwalk
🐬 Charter fishing trips in the "World's Luckiest Fishing Village"
🐬Bicycle the paved path at 30A
🐬Visit the town of Seaside where they filmed The Truman Show
🐬Enjoy the farmer's market at Rosemary Beach
🐬Pamper yourself with a massage at The Pearl
🐬Wind down from your beach day at a microbrewery
🐬Join your fellow Swifties and see why Taylor Swift sings about Destin in her song Florida!!!
reviews
★★★★★
This place was PERFECT for our large group!! The hosts were wonderful communicators, proactive and super friendly! We felt welcome and right at home. The pool was steps out the front door and an easy walk to the beach. We felt safe and LOVED the location. I’d come back ten times over! Thank you for a WONDERFUL experience!-Mary from Mississippi
★★★★★
This was the best !! Super clean, spacious, well furnished, and equipped. The host was extremely kind and helpful for anything we needed- Karen from Nashville
★★★★★
We brought the entire family down from Ohio for a quick 5 day break. House was very spacious and 50 feet from the pool. Owners were very responsive, house was very clean, beds were super comfy. TV’s in every room and 2nd living room plus mini bar on 2nd floor.-Adam from Ohio
plan your vacation today
Book Now
Book now, or contact us through the AirBnB app!
who are we?
About Us
The Sailing Dream is owner run and operated by Jenn and Shannon. We are married Air Force officers who met in Destin. We hope you'll enjoy your stay at our home.© 2026 The Sailing Dream Destin. All rights reserved.