Photo by Anthony Creamer

Chipley Holiday Rentals

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Holiday Rentals in Chipley

Condo, 2 Bedrooms | Beach
Origin at Seahaven
4.0 star property
8.8 out of 10, Excellent, (17)
"Elevator was broke, ac was working properly "
The price is NZ$480
includes taxes & fees
9 Jun - 10 Jun
Origin at Seahaven
Condo, Multiple Beds, Balcony, Ocean View (1131)
Emerald Beach Resort by Southern Vacation Rentals
3.5 star property
7.6 out of 10, Good, (754)
"This condo is very nice. It just needed a deeper cleaning. Wonderful stay. Right on the beach is nice and i sure got a lot of exercise walking from parking garage to room. Out of 5 stars i give 4."
Emerald Beach Resort by Southern Vacation Rentals
Condo, 3 Bedrooms, Beachfront (817) | Balcony view
Tidewater Beach Resort by Panhandle Getaways
3.5 star property
7.2 out of 10, Good, (119)
"I just didn’t like elevator it takes too long of waiting "
The price is NZ$1,188
includes taxes & fees
5 Jun - 6 Jun
Tidewater Beach Resort by Panhandle Getaways
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Pool
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
4.0 star property
8.0 out of 10, Very good, (21)
"Everything was amazing "
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
Pool
Edgewater Beach and Golf Resort by Southern Vacation Rentals
4.0 star property
7.4 out of 10, Good, (2162)
"The condo was perfect for our stay. 2 bathrooms is awesome. The balcony with ocean and beach view made for the perfect perch when not down by the water. The main pool area had some policies that I did not care for. Specifically, are not permitted to be turned to face the sun. Of course if you want to rent a cabana then there are perks. 🙄 Great stay and I look forward to a return trip."
Edgewater Beach and Golf Resort by Southern Vacation Rentals
Aerial view
Newly Remodeled!! 500 Feet to Beach!!
9.6 out of 10, Exceptional, (5)
"Great stay with everything that was needed. Host was amazing with communication. Would definitely recommend and would stay here again."
Newly Remodeled!! 500 Feet to Beach!!
Aerial view
Newly Remodeled Two bedroom Two bath! 500 Feet to Beach!
9.4 out of 10, Exceptional, (11)
"This was the most relaxing vacation rental. One of the ceiling fans didnt work. The property manager had it relaced immediately. Service at this beautiful rental is top notch! Cant wait till our next visit!"
Newly Remodeled Two bedroom Two bath! 500 Feet to Beach!
On the beach, white sand
Continental Condominiums by Southern Vacation Rentals II
3.5 star property
6.8 out of 10, (450)
"Quiet, great family environment. Nice beach, RIGHT on the water! Heated pool."
Continental Condominiums by Southern Vacation Rentals II
Condo, 1 Bedroom, Sea View (403E) | View from room
Splash Beach Resort by Panhandle Getaways
3.5 star property
7.0 out of 10, Good, (164)
"Everything was as good as it could be. "
The price is NZ$1,155
includes taxes & fees
2 Jun - 3 Jun
Splash Beach Resort by Panhandle Getaways
Exterior
Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.
8.6 out of 10, Excellent, (41)
"Nice room with a nice view! The weather and the waves were perfect. The laundry was right by us which was handy so no dirty clothes to bring home!"
The price is NZ$361
includes taxes & fees
3 Jun - 4 Jun
Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.
Condo, 2 Bedrooms, Sea View (1-307) | View from room
Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
8.2 out of 10, Very good, (69)
"Overall the room and everything. Personally being a business owner.I like to know all fees up front. I was a little thrown off after. The cancelation period had passed.I received a email for additional 50.00 for parking pass And wristbands I've stayed down florida many times and this is the first time that I had to deal with that over the net great trip"
The price is NZ$1,247
includes taxes & fees
12 Jun - 13 Jun
Grand Panama Beach Resort by Panhandle Getaways
Beach nearby
🏖️300 feet to the beach - Remodeled - FREE Tkts to ACTIVITIES! West PCB!🏖️
9.6 out of 10, Exceptional, (8)
"This is THE hidden gem of the Emerald Coast! Booking literally took less than 20 minutes. The unit was exceptionally clean, neat and in order. You are within walking distance of Pier Park and soo much more! You can get up, get dressed and take a 5 to 10 minute walk to Coconuts for breakfast. There are so many little beach shops between this hidden gem and Pier Park that it would be near impossible to name them all. There is a beach access point directly across from the condominium parking lot...
The price is NZ$744
includes taxes & fees
16 Jun - 17 Jun
🏖️300 feet to the beach - Remodeled - FREE Tkts to ACTIVITIES! West PCB!🏖️
On the beach
High-rise condo with pool, hot tub, central AC, & free WiFi
9.4 out of 10, Exceptional, (64)
"Absolutely love the Emerald Isle Resort. Staff is friendly and the beach is gorgeous. This is our second year there and we will be back next year!!"
High-rise condo with pool, hot tub, central AC, & free WiFi
Beach nearby
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
9.6 out of 10, Exceptional, (196)
"Love this place perfect location. Quite location but we have stayed here twice and both times we have had cleaning issues. Not owner fault. The owners are amazing people. We will definitely stay again and again"
The price is NZ$826
includes taxes & fees
21 Jun - 22 Jun
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
A heated pool
Gulf-front condo with balcony, beach access, hot tub, pool & gym
9.2 out of 10, Wonderful, (28)
"We enjoyed everything about this place."
Gulf-front condo with balcony, beach access, hot tub, pool & gym
Interior
2-Bed Condo Just Steps from the Sand!
7.6 out of 10, Good, (7)
"Great all but owners wouldn't contact me back"
2-Bed Condo Just Steps from the Sand!
Beach/ocean view
“On the Sands” Luxury Beach front Townhouse – 4BR/4 BA (8 beds and sleeps 14)
9.6 out of 10, Exceptional, (29)
"Limited parking but condo was great, easy access to beach, restaurants and events"
“On the Sands” Luxury Beach front Townhouse – 4BR/4 BA (8 beds and sleeps 14)
Property grounds
🏖️Updated BEACHFRONT condo where tropical days are just a moment away!🏖️
9.6 out of 10, Exceptional, (86)
"Good location, quiet area of the beacch. Family oriented"
The price is NZ$1,588
includes taxes & fees
16 Jun - 17 Jun
🏖️Updated BEACHFRONT condo where tropical days are just a moment away!🏖️
On the beach
GULF FRONT Master BR in Sunrise Beach with AMAZING VIEWS! Sleeps 7!
9.6 out of 10, Exceptional, (5)
"Great location on Front Beach Rd. Master bathroom was great. Had a group of adult men in town for an athletic event and had no problems with sleeping arrangements but would definitely be more geared toward a family with young kids. Would stay again."
GULF FRONT Master BR in Sunrise Beach with AMAZING VIEWS! Sleeps 7!
On the beach, sun-loungers
Beachfront Condo With Free Beach Chairs & Umbrella Set Up
9.8 out of 10, Exceptional, (63)
"We enjoyed our long weekend stay at this condo. It was very nice and exactly as described and perfect for my husband and me. The host is very friendly and helpful and made the check in/out process easy. The resort is large and was very busy, so the elevators were always at capacity. Parking is across the street, which adds to travel time once the elevators get you to the main floor. In spite of these drawbacks, we will definitely book this condo again."
Beachfront Condo With Free Beach Chairs & Umbrella Set Up
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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.

Other types of properties in Chipley you may be interested in

Iron/ironing board, free WiFi, bed sheets
Palmetto Beachfront Hotel, a By the Sea Resort
2.0 star property
8.8 out of 10, Excellent, (1002)
"Nice place for a night. Our room was across the street from the main building. Room is a little dsted but clean. There was a full sized stove and refrigerator in tje room. "
The price is NZ$316
includes taxes & fees
30 May - 31 May
Palmetto Beachfront Hotel, a By the Sea Resort
Outdoor pool, pool loungers
Seahaven Beach Hotel
2.0 star property
5.4 out of 10, (1333)
"Nice"
The price is NZ$385
includes taxes & fees
30 May - 31 May
Seahaven Beach Hotel
Exterior
Radisson Panama City Beach - Oceanfront
3.0 star property
7.4 out of 10, Good, (1508)
"Excellent! I will be a returning customer!"
The price is NZ$491
includes taxes & fees
4 Jun - 5 Jun
Radisson Panama City Beach - Oceanfront
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chipley holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chipley. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chipley. Seeing all the best attractions is bound to make you fall in love with Chipley. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chipley short-term rentals, that won’t be hard to do.

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?

2000.00 a month Winter Rental! Newly Remodeled!! 500 Feet to Beach!!: This holiday home rental outside of Chipley is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chipley?

Choose from 6 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. Pal's Park and Moss Hill Methodist Church are other places to visit while you're in town.

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.

Recent reviews of Chipley properties
Expedia verified reviews