Search Vacation Homes in Bailey's Prairie

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Our top choices for Bailey's Prairie vacation homes

Fisherman’s Dream: Canal Front Home & Views

Fisherman’s Dream: Canal Front Home & Views
Surfside
9.8 out of 10, Exceptional, (7)
$295 nightly
The price is $329
Dec 11 - Dec 12
Total with taxes and fees
Fisherman’s Dream: Canal Front Home & Views

Cozy Canal-Front Beach Bungalow with Amazing Views

Cozy Canal-Front Beach Bungalow with Amazing Views
Surfside
8.4 out of 10, Very Good, (77)
"Enjoyed staying here!"
United States
Jesus S.
$210 nightly
The price is $234
Dec 11 - Dec 12
Total with taxes and fees
Cozy Canal-Front Beach Bungalow with Amazing Views

Beach Getaway with Game Room & Tiki Bar

Beach Getaway with Game Room & Tiki Bar
Surfside
8.8 out of 10, Excellent, (40)
"Big nice place 3 family stayed and plenty of room"
United States
ronnie h.
$228 nightly
The price is $250
Dec 11 - Dec 12
Total with taxes and fees
Beach Getaway with Game Room & Tiki Bar

Beach Getaway with Deck, Steps from the Beach

Beach Getaway with Deck, Steps from the Beach
Surfside
9.2 out of 10, Wonderful, (55)
"We really enjoyed our stay! The house was perfect for our group! "
United States
Krista Z.
$235 nightly
The price is $258
Dec 11 - Dec 12
Total with taxes and fees
Beach Getaway with Deck, Steps from the Beach

Serenity Sol ※ Surfside Charmer Near Beach & Jetty

Serenity Sol ※ Surfside Charmer Near Beach & Jetty
Surfside Beach
9.4 out of 10, Exceptional, (27)
"Perfect spot for our family of three"
United States
Kelly C.
Serenity Sol ※ Surfside Charmer Near Beach & Jetty

Seabreeze Sueños ※ Surfside Abode a Walk to Beach

Seabreeze Sueños ※ Surfside Abode a Walk to Beach
Surfside Beach
9.8 out of 10, Exceptional, (61)
"We enjoyed this home for our vacation."
United States
Gary C.
Seabreeze Sueños ※ Surfside Abode a Walk to Beach

Spacious Home with Deck, Steps to the Beach

Spacious Home with Deck, Steps to the Beach
Surfside
8.8 out of 10, Excellent, (39)
"Check-in was easy and the owner was readily available for questions about the unit. It was clean and comfortable and near the beach. We enjoyed sitting on the front porch in the evening and the summer breeze. We enjoyed our stay very much! "
United States
Sara C.
$238 nightly
The price is $262
Dec 11 - Dec 12
Total with taxes and fees
Spacious Home with Deck, Steps to the Beach

Cozy Island Beach Retreat

Cozy Island Beach Retreat
Surfside Beach
9.8 out of 10, Exceptional, (6)
"Was in the perfect spot only five minutes from the beach no hassle with stay "
United States
Alyssa C.
$149 nightly
The price is $157
Dec 11 - Dec 12
Total with taxes and fees
Cozy Island Beach Retreat

Beautiful coastal home recently renovated and ready for travelers

Beautiful coastal home recently renovated and ready for travelers
Surfside Beach
10.0 out of 10, Exceptional, (120)
"Loved our stay at Midnight Sands. Host was accommodating and property was just as described. Would stay again for sure! "
United States
Terry T.
$266 nightly
The price is $292
Dec 11 - Dec 12
Total with taxes and fees
Beautiful coastal home recently renovated and ready for travelers

Budget Friendly Beach Pad for Sand, Surf, Fishing!

Budget Friendly Beach Pad for Sand, Surf, Fishing!
Surfside Beach
10.0 out of 10, Exceptional, (4)
"Clean, quiet place, enjoy are stay."
United States
Shandria M.
$363 nightly
The price is $398
Jan 2 - Jan 3, 2026
Total with taxes and fees
Budget Friendly Beach Pad for Sand, Surf, Fishing!

Spacious Home with Game Room, Deck & Bunk Room

Spacious Home with Game Room, Deck & Bunk Room
Surfside
9.0 out of 10, Wonderful, (74)
"My family and I had a great time during our stay. There was an issue with the pool but the host was able to resolve it on the same day. "
United States
Joseline L.
$407 nightly
The price is $446
Dec 11 - Dec 12
Total with taxes and fees
Spacious Home with Game Room, Deck & Bunk Room

Cozy A-frame with Gulf View, Yard & Fire Pit

Cozy A-frame with Gulf View, Yard & Fire Pit
Surfside
$242 nightly
The price is $266
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy A-frame with Gulf View, Yard & Fire Pit

Charming Beach Home Near Beach & Pier with Deck

Charming Beach Home Near Beach & Pier with Deck
Surfside
9.0 out of 10, Wonderful, (37)
"great pool, nice living area and kitchen. short walk to the beach (5 minutes), was a great stay"
United States
Stan C.
$271 nightly
The price is $297
Dec 14 - Dec 15
Total with taxes and fees
Charming Beach Home Near Beach & Pier with Deck

Blue Sea Star- I__Steps Away to beach- Dec19-28 Xmas week sale _185nt + 10%off

Blue Sea Star- I__Steps Away to beach- Dec19-28 Xmas week sale _185nt + 10%off
Surfside Beach
9.2 out of 10, Wonderful, (178)
"Everything about the stay was great! The only thing I could wish for was a little better coffee "
United States
Emalei H.
$264 nightly
The price is $290
Dec 15 - Dec 16
Total with taxes and fees
Blue Sea Star- I__Steps Away to beach- Dec19-28 Xmas week sale _185nt + 10%off

Decorated For Christmas | Private Beach Access | Luxury | Special Offer

Decorated For Christmas | Private Beach Access | Luxury | Special Offer
Surfside
9.8 out of 10, Exceptional, (9)
"The home is as described and centrally located near restaurants and popular local ice cream spot. Quaint beachfront excursion. "
United States
Isabella N.
$368 nightly
The price is $400
Dec 16 - Dec 17
Total with taxes and fees
Decorated For Christmas | Private Beach Access | Luxury | Special Offer

Shark Shack sleeps 9 people 🤩 gorgeous ocean view from house

Shark Shack sleeps 9 people 🤩 gorgeous ocean view from house
Surfside Beach
7.0 out of 10, Good, (27)
"Good place"
United States
Kyle D.
$333 nightly
The price is $365
Dec 11 - Dec 12
Total with taxes and fees
Shark Shack sleeps 9 people 🤩 gorgeous ocean view from house

Beach Views from 2 Decks. Last Minute Openings and Reduced Rates. Book Now!

Beach Views from 2 Decks. Last Minute Openings and Reduced Rates. Book Now!
Surfside Beach
10.0 out of 10, Exceptional, (77)
"Perfect stay for a mom/daughter getaway! Friendly host, great beach access, felt safe- will definitely return."
United States
Tracy H.
Beach Views from 2 Decks. Last Minute Openings and Reduced Rates. Book Now!

Charming Beach Bungalow with Deck, Close to Beach

Charming Beach Bungalow with Deck, Close to Beach
2.0 star property
Surfside
$180 nightly
The price is $197
Dec 15 - Dec 16
Total with taxes and fees
Charming Beach Bungalow with Deck, Close to Beach

The Beach and Surf is Just Steps Away.

The Beach and Surf is Just Steps Away.
Surfside Beach
10.0 out of 10, Exceptional, (127)
"Nice house, nice neighborhood, right next to the beach"
United States
Rebecca C.
$306 nightly
The price is $322
Dec 14 - Dec 15
Total with taxes and fees
The Beach and Surf is Just Steps Away.

Surfside Retreat - Great Views & Steps from Beach

Surfside Retreat - Great Views & Steps from Beach
2.0 star property
Freeport
10.0 out of 10, Exceptional, (15)
"Great location! Had everything we needed for our family vacation. Would definitely stay here again! "
United States
Lori M.
$433 nightly
The price is $433
Dec 11 - Dec 12
Total with taxes and fees
Surfside Retreat - Great Views & Steps from Beach
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.
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Top Bailey's Prairie Hotel Reviews

Find out more about Bailey's Prairie

Bailey's Prairie Vacation Homes information

Number of reviews
938
Accommodation
544 Vacation Homes
Lowest Price
$157
Highest Price
$446

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