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Chipley Holiday Rentals

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Holiday Rentals in Chipley

Calypso Beach Resort by Panhandle Getaways
3.5 star property
8.8 out of 10, Excellent, (166)
"Randomly booked a solo trip here by myself and had a great time!! Walking distance to everything, views from the balcony and beach were beautiful! Definitely a vibe and will book again"
Calypso Beach Resort by Panhandle Getaways
Tidewater Beach Resort by Panhandle Getaways
3.5 star property
7.2 out of 10, Good, (172)
"There was a little construction going on, but it wasn’t bad. Our stay was great. Communication was awesome. They got back to you in a short amount of time. There was a few issues, but nothing major."
Tidewater Beach Resort by Panhandle Getaways
Margaritaville Beach Cottage Resort PCB
4.5 star property
9.4 out of 10, Exceptional, (9)
"This property was amazing. The restaurant had great tasting food with nice size portions. The bungalow was cute, clean and the bed was so comfortable. I traveled with my family and we will be returning soon. This place gets 5 stars from me!!"
Margaritaville Beach Cottage Resort PCB
Splash Beach Resort by Panhandle Getaways
3.5 star property
7.4 out of 10, Good, (199)
"We loved this property and all the employees was very nice and friendly and we will always stay here when we come to Florida every year. Thank you for giving us a nice stay. "
Splash Beach Resort by Panhandle Getaways
Sterling Breeze by Panhandle Getaways
3.5 star property
8.4 out of 10, Very good, (31)
"Great place.. near the pier "
Sterling Breeze by Panhandle Getaways
Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
8.4 out of 10, Very good, (99)
"Definitely would stay again! Clean, nice, beautiful views! Would definitely recommend to others "
Grand Panama Beach Resort by Panhandle Getaways
Emerald Beach Resort by Southern Vacation Rentals
3.5 star property
7.6 out of 10, Good, (808)
"Great place for a relaxing beach vacation!"
Emerald Beach Resort by Southern Vacation Rentals
Edgewater Beach and Golf Resort by Southern Vacation Rentals
4.0 star property
7.4 out of 10, Good, (2201)
"Great place to stay"
Edgewater Beach and Golf Resort by Southern Vacation Rentals
Edgewater Beach & Golf Resort by Panhandle Getaways
3.5 star property
7.6 out of 10, Good, (39)
"Balcony overlooking pool was amazing! Spacious, clean and perfect for our group!"
Edgewater Beach & Golf Resort by Panhandle Getaways
Calypso Tower 3 by Panhandle Getaways
3.5 star property
8.6 out of 10, Excellent, (18)
"Wonderful stay!"
Calypso Tower 3 by Panhandle Getaways
Emerald Isle Beach Resort by Panhandle Getaways
3.5 star property
9.0 out of 10, Wonderful, (45)
"Stayed in 1902. Beautiful condo! Enjoyed sitting on the balcony every morning while drinking my coffee. Loved getting 2 beach chairs and umbrella as part of the package. Will stay here again!!"
Emerald Isle Beach Resort by Panhandle Getaways
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
4.0 star property
8.2 out of 10, Very good, (60)
"Although the the gulf was not visible from my room it was so close to the pedestrian bridge to walk to the beach and if you didn’t want to walk there were courtesy gulf cart trams to transport you. Very satisfied. "
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
Emerald Beach Resort by Panhandle Getaways
3.5 star property
8.4 out of 10, Very good, (28)
"Condo was great, very clean."
Emerald Beach Resort by Panhandle Getaways
Gulf-Front Beauty-Sleeps 12-Superb Beach Access-Heartfelt Hospitality
10.0 out of 10, Exceptional, (176)
"This home was in a great location, beautiful beach, very clean and comfortable! "
Gulf-Front Beauty-Sleeps 12-Superb Beach Access-Heartfelt Hospitality
Splash Resort
3.5 star property
8.0 out of 10, Very good, (3)
"Very nice with children"
Splash Resort
L👀K!!! ⭐️ TOP RATED CONDO ⭐️ 3 Pools ⭐️ Breathtaking Ocean Views !!!
9.8 out of 10, Exceptional, (76)
"Condo was the perfect size for our family and very clean! Close to the beach and other places. We had a great time! "
L👀K!!! ⭐️ TOP RATED CONDO ⭐️ 3 Pools ⭐️ Breathtaking Ocean Views !!!
2-Bed Condo Just Steps from the Sand!
8.4 out of 10, Very good, (25)
"I would love to stay there again and I would recommend y’all to anyone thank yall "
2-Bed Condo Just Steps from the Sand!
"Tide Life" - Perfect Sized Family Beach House
10.0 out of 10, Exceptional, (25)
"Beautiful place. Couldn’t ask for a more beautiful View. Easy check in and out. "
"Tide Life" - Perfect Sized Family Beach House
BEACHFRONT-4 Bedrm 4 BA Condo-Open SEPTEMBER-Save $$$-500 sq ft Beach BALCONY!
8.8 out of 10, Excellent, (32)
"Perfect for a family vacation location was close to everything but enough away from the crowds. We watched dolphins off the awesome patio everyday would stay again!"
BEACHFRONT-4 Bedrm 4 BA Condo-Open SEPTEMBER-Save $$$-500 sq ft Beach BALCONY!
"Envy of the Gulf" PCB #606 1 Bedroom Sleeps 6
9.6 out of 10, Exceptional, (8)
"Nice condo, nice resort, close to everything. "
The price is AU$556
includes taxes & fees
19 Oct - 20 Oct
"Envy of the Gulf" PCB #606 1 Bedroom Sleeps 6
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 Chipley Hotel Reviews

Find out more about Chipley

Everything you need to know about Chipley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chipley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chipley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chipley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chipley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley holiday rentals we have selected for you start as low as AU$556 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chipley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chipley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chipley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chipley?

Yes, there are holiday rentals close to the most popular sights in Chipley, or you can select a more secluded option if you're looking for a relaxing stay. Chipley is known for its churches and lake views. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Chipley has to offer?

Private Luxury Ocean Front 4BR/4BA Home PCB - Walk to Pier Park - Pet Friendly!: This holiday home rental outside of Chipley is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Chipley?

Choose from 10 Expedia holiday rentals in Chipley for a memorable holiday.

What can I see and do in Chipley?

Falling Waters State Park and Lucas Lake are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Pal's Park and Moss Hill Methodist Church.

What are holiday rentals like in Chipley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chipley. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.