Search Cottages in Watersound

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Watersound

Our top choices for Watersound cottages

Cottages Christian Retreat

3.0 star property
9.2 out of 10, Wonderful, (42)
"Great place to stay close to the beach, price "
Cottages Christian Retreat

PRIVATE BEACH/POOL ACCESS-Ultimate Getaway-Gulf Views-Steps to Beach-2 Bikes

10.0 out of 10, Exceptional, (86)
"The property is in a perfect location, a few minute walk to the main drag and came with all the amenities we were looking for - especially the beach chairs and cooler. Would highly recommend."
PRIVATE BEACH/POOL ACCESS-Ultimate Getaway-Gulf Views-Steps to Beach-2 Bikes

Pet &, Kid Friendly, Two FREE adult trikes (bikes) PARKING NO WORRIES

9.8 out of 10, Exceptional, (197)
"We enjoyed our stay everything was as listed great location within Rosemary beach."
The price is AED 823
AED 1,629 total
includes taxes & fees
14 Sep - 15 Sep
Pet &, Kid Friendly, Two FREE adult trikes (bikes) PARKING NO WORRIES

'Cozy for Two' - Delightful for a Couple

10.0 out of 10, Exceptional, (411)
"Absolutely wonderful place to stay! Very clean!Enjoyed our stay and will be back!!"
'Cozy for Two' - Delightful for a Couple

PRIVATE BEACH/POOL ACCESS-Steps to the Beach-Outdoor Courtyard-2 bikes

10.0 out of 10, Exceptional, (160)
"Steps to the beach and dining. Cozy yet airy and fresh. Would recommend. "
PRIVATE BEACH/POOL ACCESS-Steps to the Beach-Outdoor Courtyard-2 bikes

Florida Fun on 30A steps from Rosemary & Alys Beach Fun Lagoon Pool 4 Free Bikes

10.0 out of 10, Exceptional, (172)
"Loved this place! Short walk to the pool, village center and beach - even with a 5 and 8 year old. "
Florida Fun on 30A steps from Rosemary & Alys Beach Fun Lagoon Pool 4 Free Bikes

Jolly Roger: Amazing Rosemary Carriage Home South of 30A

9.2 out of 10, Wonderful, (57)
"Excellent location that is close to the beach walkover as well as the central square. Perfect for a couple or parents with young kids and the property manger was very responsive. The second floor outdoor deck is a great location to enjoy the evening breeze. "
Jolly Roger: Amazing Rosemary Carriage Home South of 30A

One Bedroom Guest Cottage in Seaside, 8 Houses to Beach + 2 Adult Bikes!

9.6 out of 10, Exceptional, (37)
"We loved our stay here. The place was clean and had everything we needed. The location was awesome. The staff was amazing and very responsive. We highly recommend it!"
One Bedroom Guest Cottage in Seaside, 8 Houses to Beach + 2 Adult Bikes!

150 Steps to The Beach. Book Your Last-Minute Summer Get Away Now!

9.6 out of 10, Exceptional, (116)
"A lovely home and just as pictured. A quiet neighborhood of pretty cottages but close enough to all the sights on 30A. Loved that every bedroom had its own bathroom! Thoroughly enjoyed our stay! "
150 Steps to The Beach. Book Your Last-Minute Summer Get Away Now!

EXQUISITE WATERCOLOR CARRIAGE HOUSE! SLEEPS 2-4-COME TO THE BEACH & ENJOY 30A!!

10.0 out of 10, Exceptional, (191)
"Beth was an outstanding hostess. Our family of 3 loved our time in Watercolor for the long weekend. The carriage house was comfortable and peaceful, and we were able to easily bike or walk to Seaside, the beach, Grayton Beach, and the surrounding Watercolor neighborhood! We would love to return someday soon!"
The price is AED 1,377
AED 2,692 total
includes taxes & fees
2 Oct - 3 Oct
EXQUISITE WATERCOLOR CARRIAGE HOUSE! SLEEPS 2-4-COME TO THE BEACH & ENJOY 30A!!

The Smith House - Updated Historic Charm

10.0 out of 10, Exceptional, (265)
"The island and the beaches are fantastic. The house has all the charm and peace to top off a wonderful location. "
The Smith House - Updated Historic Charm

Romantic Dog-Friendly Cottage with Shared Pool, Beach Access, & Plenty of Charm

8.4 out of 10, Very Good, (141)
"Great time!"
The price is AED 606
AED 1,807 total
includes taxes & fees
14 Sep - 15 Sep
Romantic Dog-Friendly Cottage with Shared Pool, Beach Access, & Plenty of Charm

Key Lime Cottage - 1930's 2 bed 2 bath beach cottage - Steps from the Sand

9.8 out of 10, Exceptional, (118)
"Our favorite beach! This house is so close to the beach and extra points because it’s also across from the best donuts! Booking again soon for 2026 trip! "
Key Lime Cottage - 1930's 2 bed 2 bath beach cottage - Steps from the Sand

Prime Seaside location 59 ft to Beach Access, 2 Min to Amphitheater + 2 Bikes

9.2 out of 10, Wonderful, (31)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The convenience to the beach and the amphitheater area makes this cottage so sweet. Though small, it’s perfect for a couple or a single traveler. I would definitely stay here again."
Prime Seaside location 59 ft to Beach Access, 2 Min to Amphitheater + 2 Bikes

New Rosemary Beach Carriage, Bright & South of 30-A

9.4 out of 10, Exceptional, (11)
"The property had everything we need and was in a beautiful location near the beach and town. We’d definitely stay there again. "
New Rosemary Beach Carriage, Bright & South of 30-A

PRIVATE BEACH ACCESS-2 Minute Walk-Stunning South Side Retreat-Courtyard/Pool

10.0 out of 10, Exceptional, (32)
"We hd a great stay for the second time around. Fantastic location, pool was wonderful to have with the kiddos. A very family friendly trip. Highly recommend. "
PRIVATE BEACH ACCESS-2 Minute Walk-Stunning South Side Retreat-Courtyard/Pool

Madison Cottage, South of 30-A in Rosemary Beach. Close to Beach, Pool and Shoppes.

10.0 out of 10, Exceptional, (69)
"This home was spacious, spotless and convenient to the beach! Would stay here again for sure!"
Madison Cottage, South of 30-A in Rosemary Beach. Close to Beach, Pool and Shoppes.

BEACH FRONT LOWER PRIVATE COTTAGE, 2BD2BA, X Large Deck, FREE Private Parking

9.8 out of 10, Exceptional, (70)
"We thoroughly enjoyed this cottage. The beautiful ocean views and easy access to the beach make this one a favorite for our family. The hosts were so friendly and welcoming. Thank you for allowing us to make such wonderful memories here. "
BEACH FRONT LOWER PRIVATE COTTAGE, 2BD2BA, X Large Deck, FREE Private Parking

PRIVATE BEACH/POOL ACCESS-Cozy Getaway Retreat For Two with Two Bikes

9.8 out of 10, Exceptional, (88)
"Lovely place nice clean walking distance to the beach pool and food. Very pleased "
PRIVATE BEACH/POOL ACCESS-Cozy Getaway Retreat For Two with Two Bikes

'Lazy Magnolia' - Close to Beach & Pool w/4 Bikes & Beach Chairs! Near Rosemary!

10.0 out of 10, Exceptional, (121)
"This was perfect for our family-close to the beach and the community pool was a hit with the kids. Great location for families with young children, the neighborhood seemed very family oriented and safe. It was great to have beach chairs, umbrellas and wagon to use for beach days. We also enjoyed the bicycles and there are great bike trails close by. "
'Lazy Magnolia' - Close to Beach & Pool w/4 Bikes & Beach Chairs! Near Rosemary!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Watersound Hotel Reviews

Frequently asked questions

Why book your cottage in Watersound with Expedia?
Reserving a cottage in Watersound is as simple as working out your travel dates and selecting an ideal place for a getaway in the outdoors. From luxurious retreats to budget-friendly stays and cottages that feature conveniences like a kitchen, Expedia has something for all tastes. As for epic deals? We've got them too!
How can I find cheap cottages in Watersound?
With Expedia's helpful filter tool, scoring cheap cottages in Watersound is a snap. To find properties that'll make your wallet happy, tailor your search results by budget, amenities and star rating.