Photo by Anthony Creamer

Chipley Vacation Rentals

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Vacation Rentals in Chipley

Origin at Seahaven
4.0 star property
8.8 out of 10, Excellent, (17)
"Elevator was broke, ac was working properly "
The price is ¥13,130
per night
Jun 5 - Jun 6
Origin at Seahaven
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
Tidewater Beach Resort by Panhandle Getaways
3.5 star property
7.2 out of 10, Good, (120)
"I just didn’t like elevator it takes too long of waiting "
The price is ¥26,429
per night
Jun 5 - Jun 6
Tidewater Beach Resort by Panhandle Getaways
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Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
4.0 star property
8.0 out of 10, Very Good, (21)
"Great resort!"
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
Edgewater Beach and Golf Resort by Southern Vacation Rentals
4.0 star property
7.4 out of 10, Good, (2163)
"The condo unit was absolutely beautiful and the view was incredible right on the beach. The sand is pure white like powder sugar and the turquoise water is gorgeous. The staff at Southern Vacation Rentals were available in person day and night to answer any questions we had. We will definitely come back. "
Edgewater Beach and Golf Resort by Southern Vacation Rentals
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!!
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!
Continental Condominiums by Southern Vacation Rentals II
3.5 star property
6.8 out of 10, (450)
"Everything was good "
Continental Condominiums by Southern Vacation Rentals II
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 ¥32,928
per night
Jun 6 - Jun 7
Splash Beach Resort by Panhandle Getaways
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 ¥14,001
per night
Jun 3 - Jun 4
Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.
Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
8.2 out of 10, Very Good, (70)
"This place was very clean! The staff was nice, it’s conveniently located to grocery stores and shops! Will definitely be back. "
The price is ¥36,181
per night
Jun 8 - Jun 9
Grand Panama Beach Resort by Panhandle Getaways
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
9.6 out of 10, Exceptional, (196)
"Location was amazing. :)"
The price is ¥31,462
per night
Jun 7 - Jun 8
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
Beachfront Condo With Free Beach Chairs & Umbrella Set Up
9.8 out of 10, Exceptional, (64)
"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
🏖️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 ¥21,237
per night
Jun 16 - Jun 17
🏖️300 feet to the beach - Remodeled - FREE Tkts to ACTIVITIES! West PCB!🏖️
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
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
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!
Tidewater Beach Luxury Penthouse w/ Resort Amenities and a View!
9.2 out of 10, Wonderful, (23)
"Loved the place and location but the elevators were the worst, took us 30 minutes every time we had to use it and being on the 25th floor did not help. We had to take the stairs a couple times which was absolute hell carrying items up and down to the beach."
The price is ¥46,726
per night
Jun 21 - Jun 22
Tidewater Beach Luxury Penthouse w/ Resort Amenities and a View!
Calypso 902 West - 3 Bedroom, 2 Bathroom Beach Front Condominium
6.4 out of 10, (27)
"I have been stuck at home for six months and this was my first time out since my health crisis. We have stayed at the Calypso in many different units over the years, we have been coming to the Calypso for going on 13 years always a great time staying here have not had a problem at any other units. I would say that there is very little deck furniture only one chair. And the beds are hard but other than that it’s all good. PS the dryer takes forever to dry your clothes."
Calypso 902 West - 3 Bedroom, 2 Bathroom Beach Front Condominium
Steps to the beach! 2 br/1 bath Sleeps 6, ground floor Condo
9.6 out of 10, Exceptional, (40)
"The unit was exactly as pictured. Everything was clean and well appointed. We had return home sooner than expected due to unforeseen issues, so we weren't able to explore the whole area like we had planned."
Steps to the beach! 2 br/1 bath Sleeps 6, ground floor Condo
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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

Seahaven Beach Hotel
2.0 star property
5.4 out of 10, (1343)
"This place could be a lot nicer if they would put just a few improvements. It definitely needs some work. It wasn’t bad for the cost. The view is worth it all. "
The price is ¥31,203
per night
Jun 2 - Jun 3
Seahaven Beach Hotel
Palmetto Beachfront Hotel, a By the Sea Resort
2.0 star property
8.8 out of 10, Excellent, (1006)
"My family and I recently stayed at the Palmetto we have no complaints. The property is a bit dated however; the hotel location and direct private beach access was great. I would ask if you could kindly provide more accessible towels at the pool area that would be awesome. I would definitely be back next summer same property. "
The price is ¥15,447
per night
Jun 4 - Jun 5
Palmetto Beachfront Hotel, a By the Sea Resort
Radisson Panama City Beach - Oceanfront
3.0 star property
7.4 out of 10, Good, (1515)
"This property offers so much for a getaway. Kitchen, with all the utensils you need, a balcony with amazing beach views, comfortable beds and youre near anything and everything for eats, grocery shopping and plenty of places to shop for souvenirs and whatever else you desire. Will definitely be back!"
The price is ¥41,859
per night
Jun 4 - Jun 5
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.

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Frequently asked questions

Can I find vacation rentals in Chipley?

Yes, there are vacation rentals close to popular points of interest in Chipley, or you can go with a secluded option if you'd like a relaxing place to 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's the top vacation rental that Chipley has to offer?

2000.00 a month Winter Rental! Newly Remodeled!! 500 Feet to Beach!!: You might want to consider this vacation home rental near Chipley, which is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chipley?

Choose from 6 Expedia vacation rentals in Chipley for a memorable vacation.

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 vacation rentals like in Chipley?

Vacation rentals are private accommodations you can book for a couple days or more in Chipley. Vacation rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.

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