Cottages by the Bay Retreat

Destin, FL
50 Guests 18 Bedrooms 16 Full Baths

Military Appreciation

To show our appreciation for the United States Military, all Active Duty and Retired Military will SAVE on a stay with Southern using promo code MILITARY.

Offer expires 01/02/2025 and you must book your vacation between 11/05/2019 and 12/31/2025.

Cottages by the Bay Retreat ~ Destin, Florida Vacation Homes by Southern

Are you planning a corporate retreat, getaway, or family reunion in Destin, Florida? Then our Cottages by the Bay Retreat is perfect for you and your group. Come discover these idyllic, Old Florida-style homes nestled perfectly in the heart of Destin. Now, you can also rent the newest addition to the Cottages by the Bay, "At Last."

Accommodating groups both large and small, Cottages by the Bay Retreat consists of eight charming cottages situated in one community. Here, find room for up to 50 guests across 16 bedrooms. Inside each Cottage, you’ll discover the comforts of home designed to provide you with relaxation on your group retreat. Enjoy luxurious upgrades in each fully equipped kitchen and private bathroom, including stainless steel appliances and hand-laid tile.

The outdoor space at the Cottages is truly unmatched. Unwind under the stars at the outdoor fire pit, or socialize with colleagues or family members on the spacious lawn. Meetings can also be held on the lawn, providing incredible scenery among the towering oak trees. The outdoor television provides another great place to spend time with your group. Take a dip in the private pool, or head out onto Choctawhatchee Bay’s sparkling waters via the nearby boat launch at Joe’s Bayou.

Additionally, Cottages by the Bay Retreat is located just across the street from the Destin Bay House*, Northwest Florida’s premier wedding, and event venue. This is the ideal place to host any kind of event, with an indoor meeting space boasting Bay views, a screened-in porch, and large windows overlooking the natural beauty of your surroundings. The Destin Bay House also offers an outdoor lawn area for gathering, along with a private white sand beach area.

Meanwhile, you are sure to enjoy being within walking distance of many events in Destin, restaurants, and exciting activities. HarborWalk Village is located just minutes away from the Cottages, offering a variety of shopping and dining options. For additional group fun, rent a wave runner, pontoon boat, or even bicycles from La Dolce Vita, located right across the street.

When you choose Cottages by the Bay Retreat for your next corporate retreat or family reunion in Destin, you create lifelong memories that will have you returning to the area year after year. Call or book online today and begin planning the getaway of a lifetime.

Clean Coverlet Program: This property provides fresh and clean bed linens, including comforters and coverlets, laundered prior to every check-in.

  • Fire pit available from October 1 – May 15.
  • *The Destin Bay House is not available for use after June 30, 2021.
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Don't forget to bring:
While Southern provides you an initial supply of toilet paper, paper towels, hand soap, and trash bags to get you through your first 24 hours, we recommend you bring the following: paper towels, toilet paper, trash bags, hairdryer, napkins, condiments, spices, dishwashing liquid, laundry soap, coffee and coffee filters, beach towels, umbrella, beach toys, sunscreen, and anything else you may need for your perfect vacation.
  • Free WiFi
  • Self Check-in (Keyless Lock)
  • TV (s)
  • Washer
  • Dryer
  • Clean Coverlets - Every Reservation

Unit Size

  • 7700 sq. ft

Bed Types

  • King (s): 15
  • Bunk Bed (s) - Twins: 2
  • Queen Bed (s): 4
  • Sleeper Sofa (s) - Queen: 6


  • Beach Access

Property Features

  • Private Entrance
  • Linens Provided
  • Air Conditioning
  • Iron & Ironing Board
  • Smoke Detector
  • Fire Extinguisher
  • Heating

Kitchen Features

  • Dishwasher
  • Keurig Coffee Maker
  • Full Kitchen
  • Granite Countertops
  • Stainless Steel Appliances
  • Oven
  • Blender
  • Stove
  • Toaster
  • Refrigerator
  • Coffee Maker
  • Dishes & Utensils
  • Microwave

Bathroom Features

  • Walk In Shower
  • Towels (Not Beach) Provided

Resort/Community Amenities

  • Boat Slip Available
  • Community BBQ Grills
  • Community Laundry Facility

Activities Nearby

  • Boating
  • DeepSea Fishing
  • Fishing
  • Golf
  • Parasailing
  • Swimming
  • Snorkeling
  • Shopping
  • Eco Tourism
  • Sailing
  • Surfing
  • Beach Combing

Attractions Nearby

  • Restaurants
  • Cinemas
  • Health Beauty Spa
  • State Parks
  • Festivals


  • No Guests Under 25 w/o Parent
  • Wedding/Event Allowed
  • Non Smoking
  • No Pets Allowed
  • Snowbird Rentals Accepted
  • No Smoking in Complex Common Areas
  • Photo ID Required Upon Making Reservation
  • Family Friendly
  • Minimum Night Stay and Turn Day Restrictions May Apply

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