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Chipley Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Chipley

Margaritaville Beach Cottage Resort PCB
Exterior

Margaritaville Beach Cottage Resort PCB

4.5 star property
10.0 out of 10, Exceptional, (7)
"Absolutely relaxing and easy walk to beach and pool- accommodations just beautiful!"
Margaritaville Beach Cottage Resort PCB
Calypso Beach Resort by Panhandle Getaways
View from room

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
View from property

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 outdoor pools

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
View from room

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
Aerial view

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
View from room

Sterling Breeze by Panhandle Getaways

3.5 star property
8.4 out of 10, Very good, (31)
"Great place.. near the pier "
The price is HK$2,140
HK$8,126 total
includes taxes & fees
17 Oct - 18 Oct
Sterling Breeze by Panhandle Getaways
Edgewater Beach and Golf Resort by Southern Vacation Rentals
Pool

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
1 bedroom, individually decorated, individually furnished

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 outdoor pools

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
Fitness facility

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
Property amenity

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
Calypso Tower 3 by Panhandle Getaways
On the beach, white sand

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
Origin At Seahaven
2 bedrooms, individually decorated, individually furnished

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
BEACH FRONT Double King Sleeps 6, Wifi, Beach Service & under building parking!
On the beach

BEACH FRONT Double King Sleeps 6, Wifi, Beach Service & under building parking!

10.0 out of 10, Exceptional, (131)
"Our stay was amazing. The condo was everything we wanted. The view from the balcony was breathtaking. We highly recommend this beach front. "
BEACH FRONT Double King Sleeps 6, Wifi, Beach Service & under building parking!
"Tide Life" - Perfect Sized Family Beach House
Terrace/patio

"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!
Outdoor pool

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
Gym

Splash Resort

3.5 star property
8.0 out of 10, Very good, (3)
"Very nice with children"
Splash Resort
Gulf-Front Beauty-Sleeps 12-Superb Beach Access-Heartfelt Hospitality
Property grounds

Gulf-Front Beauty-Sleeps 12-Superb Beach Access-Heartfelt Hospitality

10.0 out of 10, Exceptional, (176)
"We enjoyed our stay at the property. It was nice, clean and beach convenient. A lovely property."
Gulf-Front Beauty-Sleeps 12-Superb Beach Access-Heartfelt Hospitality
Southwind Condo Rentals by Panhandle Getaways
Aerial view

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

Beachcomber Beachfront Hotel, a By The Sea Resort

Beachcomber Beachfront Hotel, a By The Sea Resort

10/10 Excellent
"Overall property needs MAJOR upgrades,Entry room door large gap under door, peeling paint, bathroom musty dirty,kitchen area filthy ,dirty discussing,pool area peeling paint ,grassey area not trimmed or mowed. Great location on the beach nice tiki bar(though closed when we were there.Nice helpfull staff.Aplogized for the state of the place!!"
JONATHAN 1-night trip
Posted 10 hours ago
Beachcomber Beachfront Hotel, a By The Sea Resort

Find out more about Chipley

Search for holiday rentals in Chipley on Expedia! You can easily find your home rentals, villas, holiday apartments in Chipley using one of the methods below:

  • View our selection of featured holiday rentals in Chipley
  • Use the map to find apartments and other holiday homes in the Chipley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chipley while they last

Look no further and take a look at our great range of rental properties in Chipley!

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.