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Chipley Holiday Rentals

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Holiday Rentals in Chipley

Margaritaville Beach Cottage Resort PCB

4.5 star property
10.0 out of 10, Exceptional, (6)
"Absolutely relaxing and easy walk to beach and pool- accommodations just beautiful!"
Margaritaville Beach Cottage Resort PCB

Calypso Beach Resort by Panhandle Getaways

3.5 star property
8.8 out of 10, Excellent, (165)
"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, (171)
"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

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

Emerald Isle Beach Resort by Panhandle Getaways

3.5 star property
9.0 out of 10, Wonderful, (44)
"Stayed in 1902 and it was very clean with an awesome view. Very nice condo facility with great parking for that unit. The facility is not new but well maintained for the amount of use it has had. Would definitely go again. "
Emerald Isle Beach Resort 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

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

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

Emerald Beach Resort by Southern Vacation Rentals

3.5 star property
7.6 out of 10, Good, (807)
"4th visit and was wonderful as always. Really enjoy staying here with my family."
Emerald Beach Resort by Southern Vacation Rentals

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

Edgewater Beach & Golf Resort by Panhandle Getaways

3.5 star property
7.6 out of 10, Good, (39)
"condo a little dated and plastic chairs for dining not good. Sofas old and worn. Beds comfortable. "
Edgewater Beach & Golf Resort by Panhandle Getaways

Edgewater Beach and Golf Resort by Southern Vacation Rentals VI

4.0 star property
8.0 out of 10, Very good, (59)
"Very helpful staff. Clean condo. Gated. "
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI

Calypso Tower 3 by Panhandle Getaways

3.5 star property
8.6 out of 10, Excellent, (17)
"Wonderful stay!"
Calypso Tower 3 by Panhandle Getaways

#A Gulf Highlands Cozy Condo-BEACH ACCESS

7.4 out of 10, Good, (10)
"It was a great place to stay for a week."
The price is NZ$320
includes taxes & fees
10 Oct - 11 Oct
#A Gulf Highlands Cozy Condo-BEACH ACCESS

"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!

Splash Resort

3.5 star property
8.0 out of 10, Very good, (3)
"Very nice with children"
Splash Resort

Origin At Seahaven

3.5 star property
7.0 out of 10, Good, (2169)
"My stay was wonderful very clean and pleasant and the staff was friendly and helpful "
Origin At Seahaven

Gulf Front Getaway-Sleeps 12-On the Beach-Experienced, Heartfelt Host

10.0 out of 10, Exceptional, (175)
"We enjoyed our stay at the property. It was nice, clean and beach convenient. A lovely property."
Gulf Front Getaway-Sleeps 12-On the Beach-Experienced, Heartfelt Host

Southwind Condo Rentals by Panhandle Getaways

3.5 star property
8.2 out of 10, Very good, (31)
"Wonderful location. Walk right across the street to the beach. Condo was clean will be back!"
Southwind Condo Rentals by Panhandle Getaways
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

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 NZ$320 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?

Celadon Beach Resort: This holiday home rental outside Chipley is located on the beach, and has an outdoor pool, a furnished balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. Kick off your shoes and enjoy yourself with an outdoor tennis court and 1 hot tub.

How many holiday rentals are there in Chipley?

Choose from 9 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.