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Chipley Holiday Rentals

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Holiday Rentals in Chipley

Landmark Holiday Beach Resort

3.5 star property
Panama City Beach
8.6 out of 10, Excellent, (219)
"Kitchen has everything you need along with washer and dryer.. Beautiful beachfront view ."
United States
Judy
Landmark Holiday Beach Resort

Margaritaville Beach Cottage Resort PCB

4.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (10)
"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!!"
United States
Malion
Margaritaville Beach Cottage Resort PCB

Grand Panama Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
8.4 out of 10, Very good, (99)
"Definitely would stay again! Clean, nice, beautiful views! Would definitely recommend to others "
United States
Maximino
Grand Panama Beach Resort by Panhandle Getaways

Splash Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
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. "
United States
Christopher
Splash Beach Resort by Panhandle Getaways

Edgewater Beach & Golf Resort by Panhandle Getaways

3.5 star property
Panama City Beach
7.6 out of 10, Good, (39)
"Balcony overlooking pool was amazing! Spacious, clean and perfect for our group!"
United States
Kara
Edgewater Beach & Golf Resort by Panhandle Getaways

Sterling Breeze by Panhandle Getaways

3.5 star property
Panama City Beach
8.4 out of 10, Very good, (31)
"Great place.. near the pier "
United States
Tina
Sterling Breeze by Panhandle Getaways

Edgewater Beach and Golf Resort by Southern Vacation Rentals

4.0 star property
Panama City Beach
7.4 out of 10, Good, (2201)
"Great place to stay"
United States
Gary
Edgewater Beach and Golf Resort by Southern Vacation Rentals

Emerald Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
8.4 out of 10, Very good, (28)
"Condo was great, very clean."
United States
Jelena
Emerald Beach Resort by Panhandle Getaways

Emerald Isle Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
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!!"
United States
Sandra
Emerald Isle Beach Resort by Panhandle Getaways

Splash Resort

3.5 star property
Panama City Beach
7.0 out of 10, Good, (4)
"Very nice with children"
United States
Susan
Splash Resort

Calypso Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (167)
"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"
United States
Amanda
Calypso Beach Resort by Panhandle Getaways

BEACHFRONT-4 Bedrm 4 BA Condo-Open SEPTEMBER-Save $$$-500 sq ft Beach BALCONY!

Panama City Beach
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!"
United States
Carla H.
BEACHFRONT-4 Bedrm 4 BA Condo-Open SEPTEMBER-Save $$$-500 sq ft Beach BALCONY!

Emerald Beach Resort by Southern Vacation Rentals

3.5 star property
Panama City Beach
7.6 out of 10, Good, (812)
"My stay was great clean rooms and the greatest staff I will be back."
United States
Lashon
Emerald Beach Resort by Southern Vacation Rentals

"Tide Life" - Perfect Sized Family Beach House

Laguna Beach Estates
10.0 out of 10, Exceptional, (25)
"Beautiful place. Couldn’t ask for a more beautiful View. Easy check in and out. "
United States
Kenneth K.
"Tide Life" - Perfect Sized Family Beach House

Tidewater Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
7.2 out of 10, Good, (175)
"The beach was beautiful! Clean and well kept!"
United States
Polly
Tidewater Beach Resort by Panhandle Getaways

Aqua Beach Resort by Panhandle Getaways

3.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (12)
"The sunsets were perfect."
United States
Nick
Aqua Beach Resort by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways

3.5 star property
Panama City Beach
8.6 out of 10, Excellent, (18)
"Wonderful stay!"
United States
Lisa
Calypso Tower 3 by Panhandle Getaways

Beachfront Condo with Amazing Views and Beach Service Included!

Panama City
10.0 out of 10, Exceptional, (2)
"The unit was clean and beautiful. My elderly in laws were very comfortable in the living room and outdoor seating options! All the beds were comfortable, even the pull out sofa got good reviews from my 9yr old! The owner was absolutely wonderful to work with and easily available and eager to help with a wifi issue we had and any questions! We will definitely be coming back next year! "
United States
Bill S.
Beachfront Condo with Amazing Views and Beach Service Included!

PANORAMIC Oceanfront Views 4 bd Condo at 2 bd rates FREE RESERVED Beach service

Panama City Beach
9.4 out of 10, Exceptional, (106)
"Highly recommend this place to stay in PCB, very clean and equipped with everything we needed for our week long stay. Spacious and extremely comfortable for our family. "
United States
Felicia P.
PANORAMIC Oceanfront Views 4 bd Condo at 2 bd rates FREE RESERVED Beach service

Edgewater Beach and Golf Resort by Southern Vacation Rentals VI

4.0 star property
Panama City Beach
8.2 out of 10, Very good, (61)
"Great place! There were a couple of things that need to be fix but nothing that was an inconvenience. The place was nice and clean and the location was excellent. Getting to the beach and pool was an easy walk or even ride on the tram that is available. The location of the property is also very close to so many places for groceries, food, and shopping. Would definitely stay here again! "
United States
Sergio
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
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 favorite 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 depends 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 per night. Entering your travel dates in the search wizard you might find 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?

Gulf-Front Beauty-Sleeps 12-Superb Beach Access-Heartfelt Hospitality: This holiday home rental outside of Chipley is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.