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USA Florida Sterling Resorts Santa Rosa Beach Listing #32775

Calypso Cottage - Sunrise Beach Subdivision - Santa Rosa Beach, FL

9 reviews
Max occupancy: 16 2 King Bed, 2 Queen Bed, 2 Double Bed, 4 Twin Bed 4 bedrooms 4 bathrooms No pets 
44 Seaward Dr, Santa Rosa Beach, FL 32459

Worry-free booking

Enjoy peace of mind with flexible options to change or cancel your trip.

If your check-in date is at least 30 days away, you can reschedule your trip, cancel and receive 100% of the cost as a Future Stay Credit, or cancel for a refund (minus the booking fee).

Expert cleaning

Professional housekeepers clean and stock each home, using an EPA-approved disinfectant.

Local support

Each trip is backed by 24/7 customer support and local teams everywhere we operate.


Many Vacasa homes use smart locks or lockboxes for a smooth, contactless check-in.

Three-story beach home with private pool, free WiFi, walk to private beach!

Calypso Cottage is a beautiful four-bedroom, four-bathroom, three-story home nestled in the gated community of Sunrise Beach in Santa Rosa Beach. This 2,360 square foot home is located within walking distance to Gulf Place, a town center with plenty of shopping and dining venues. Enjoy time with your family in your own private swimming pool or walk down to the private beach! The living area and the master bedroom both offer private balconies where you can sit back and enjoy gentle gulf breezes from the nearby emerald waters of the Gulf of Mexico. The upgraded kitchen is fully equipped, so you can prep and serve meals right at home.

The combined living and dining area offer gulf views and create an ideal place for family gatherings with its large flat-screen TV and dining that seats up to 10 people. There are two sets of king beds, two sets of queen beds, two full beds, and two bunk beds. All are equipped with flat-screen TVs. There is also a full-sized washer and dryer for your convenience. Right outside the den area is where you relax in your own private pool, with plenty of outdoor seating and a grill for those who like to cook and dine alfresco.

Being in the community of Sunrise Beach means this home is a short bike ride away from all that the west end of 30A has to offer. When you visit Gulf Place, you can dine at Pizza by the Sea, La Playa, The Perfect Pig, or Shunk Gulley's – a great seafood place overlooking the gulf. If you head into Blue Mountain Beach, you can stop at Redfish Taco or The Creamery, and try to award-winning chocolate ice cream. A longer ride east will take you to Grayton State Park or the areas of Watercolor and Seaside, where The Truman Show was filmed. No matter what brings you to Calypso Cottage, this home, the scenery, the community, and an array of local attractions will make you realize you’ve truly been in paradise, and keep you coming back again.

What’s nearby:
Enjoy local restaurants like Blue Mabel (two miles from the condo) and local favorite Shunk Gulley Oyster Bar (less than half a mile away). Grayton Beach State Park (which features the Underwater Museum of Art) is just a nine-mile drive away. 16 miles from the condo lies Deer Lake State Park, where guests can observe nature and wildlife.

Things to know:
Free WiFi and cable
Full kitchen
Free bicycle use for guests
Snowbird friendly

You must be 25 years or older to rent this property.




Washer/dryer : Private

Heating & cooling

Central AC

Kitchen & dining









DVD player

Wireless router

Nearby activities & attractions

Golf Nearby

On-site activities

Pool : Private

Adult bikes





Enclosed yard

9 reviews

Christa M. Sep 2020
pool was nice
David R. Sep 2020
Everything about this home was perfect! The location, size, beauty, cleanliness, layout, owner communication, EVERYTHING!!!!
We even loved that the kitchen was on the top floor because it was too much effort for the kids to bother us constantly for snacks, tattling, etc!!!!!
We will definitely be returning to this beach home for our future family trips, and I can’t wait to get my toes back in that white sand.
Martin G. Aug 2020
We had a wonderful beach vacation at Calypso Cottage. The house was perfect for us! The beach access is so close and the private pool was a hit with the kids. We loved that there was second living room area. The extra beach chairs and boogie boards came in handy. There were also 8 beach bikes at the house we were able to use. This house was perfect for young children.
We love staying in this small gated community. It is very close to the fun restaurants, coffee shops, and ice cream parlors.
We will definitely be back next year!
Joseph R. Jul 2020
This house was a great size, close to the beach and perfect for the pool too. Absolutely wonderful experience.
Shawn K. Jul 2020
We really enjoyed the neighborhood and how close we were to the beach. The bedroom setup was perfect for our group of 7 and we could have definitely had more people and had plenty of room. The pool was nice, but this property backs up to 3 other pools, so it is not very private. It was wonderful having 8 bikes and there were several beach chairs and floats for us to use. However, we did not like the that the kitchen and living room area were on the 3rd floor and you could not get to any bathroom without walking through a bedroom. It was a hike to get the groceries upstairs and get coolers ready, etc. It may have been a little easier if there was a larger refrigerator on the 1st floor and place to store coolers.
gaynel m s. Jul 2020
Great beach house. Plenty of room for large families. I am concerned about future beach access. Some owners are not allowing anyone on the beach in front of their house. The rest of the beach only allows canopies. I gave the house top rate but if stricter restrictions are in place next year I probably won't go back to same area.
Ann M. May 2020
I would 100% recommend this house! It is only seconds from the beach. The house was spotless with lots of perks and amenities. We loved having the pool and charcoal grill. It accommodated our large party well and the beds were very comfy. The third floor has a beautiful view of the ocean.
The owners also provided beach chairs, umbrellas, and beach bikes. It is in a central location close to several good restaurants. I can’t wait to come back!
Kizzy H. Dec 2019
We really enjoyed our stay