House
10.0(17 Reviews)
4 Bedrooms
8 Guests
Parking
Kitchen
Air Conditioner
Internet
R4,615/Night
7 Nights - R32,299
Chipley, FL Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Chipley
10.0
House
10.0(2 Reviews)
5 Bedrooms
14 Guests
Private Pool
Hot Tub
Breakfast- Parking
R2,338/Night
7 Nights - R16,374
R1,364/Night
7 Nights - R9,542
Bed & Breakfast
9.8(21 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Breakfast
- Parking
Pool
R3,143/Night
7 Nights - R21,992
House
10.0(1 Review)
4 Bedrooms
8 Guests
- Parking
- Internet
Sports/Activities
Security/Safety
R2,527/Night
7 Nights - R17,687
House
9.2(17 Reviews)
3 Bedrooms
10 Guests
- Parking
Balcony/Terrace- Kitchen
- Air Conditioner
R4,815/Night
7 Nights - R33,712
House
4.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,161/Night
7 Nights - R22,125
House
10.0(46 Reviews)
3 Bedrooms
6 Guests
- Parking
Ocean View- Balcony/Terrace
View
R4,327/Night
7 Nights - R30,287
Bed & Breakfast
10.0(23 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
R2,812/Night
7 Nights - R19,682
Luxury Holiday Rentals in Chipley
Over 27+ Luxury Holiday Rentals in or Near Chipley
R7,729/Night
7 Nights - R54,108
House
9.8(9 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R4,849/Night
7 Nights - R33,945
House
9.6(7 Reviews)
2 Bedrooms
6 Guests
Child Friendly
R3,972/Night
7 Nights - R27,811
House
9.8(6 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R3,843/Night
7 Nights - R26,896
House
9.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Internet
Pet Friendly
R3,718/Night
7 Nights - R26,032
New
House
2 Bedrooms
8 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
R3,116/Night
7 Nights - R21,810
House
9.8(14 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R2,766/Night
7 Nights - R19,366
Bed & Breakfast
10.0(1 Review)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
R2,654/Night
7 Nights - R18,585
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
R2,529/Night
7 Nights - R17,704
Top-Rated Holiday Rentals with a Pool in Chipley
Over 2+ The Best Private Villas and Holiday Rentals in Chipley with a Pool
R1,450/Night
7 Nights - R10,157
R1,347/Night
7 Nights - R9,425
Pet-Friendly Holiday Rentals in Chipley
Over 7+ Pet-Friendly Holiday Rentals in or Near Chipley
House
10.0(10 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R7,986/Night
7 Nights - R55,904
R1,080/Night
7 Nights - R7,564
R1,157/Night
7 Nights - R8,095
House
5.0(1 Review)
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
Laundry
R4,771/Night
7 Nights - R33,396
R975/Night
7 Nights - R6,832
House
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,156/Night
7 Nights - R29,091
House
3 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R4,986/Night
7 Nights - R34,909
Wheelchair Accessible Holiday Homes in Chipley
Over 1+ Wheelchair Accessible Holiday Homes in or Near Chipley
R1,187/Night
7 Nights - R8,312
Chipley Private Villas and Holiday Homes Under $200
Over 5+ Chipley Private Villas and Holiday Homes Under $200
House
10.0(10 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,929/Night
7 Nights - R20,496
R1,157/Night
7 Nights - R8,095
House
5.0(1 Review)
3 Bedrooms
8 Guests
Oceanfront- Ocean View
- Balcony/Terrace
- View
R2,410/Night
7 Nights - R16,873
Cottage
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
R3,242/Night
7 Nights - R22,691
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R2,327/Night
7 Nights - R16,291
Book a Last Minute Place to Stay in Chipley
About Casai's Private Villas and Holiday Rentals in Chipley
Discover more than 36 vacation rentals available in Chipley. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chipley.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chipley, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chipley. On average, places to stay near Chipley offer 1065.91 ft², with nightly prices averaging R3,405.
With Casai, finding and comparing holiday rentals in Chipley is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Chipley, FL
There are 36 Chipley, FL Holiday Rentals
- Prices for a holiday home in Chipley start at R975
- Top rated vacation home in Chipley is Lakefront Home, beautiful setting, only 30 minutes drive from the Beaches of 30A
- Most popular short term in Chipley is Quality Inn Chipley I-10 at Exit 120
- Cheapest place to stay in Chipley is Super 8 by Wyndham Chipley
- Most expensive holiday rental in Chipley is The Cozy Farmhouse Retreat
Recently Booked Holiday Rentals in Chipley
Frequently Asked Questions About Chipley?
What are the top holiday rentals in Chipley?
With numerous options available in Chipley, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chipley:
- Lakefront Home, beautiful setting, only 30 minutes drive from the Beaches of 30A
- Luxury Country Stay - Indoor heated pool, Spa, Art Studio, Breakfast, Hot Tub
- Vintage Chipley Getaway on Large Private Property
- Relaxing Retreat Pool, Spa, Art Studio, Breakfast
- Peaceful Romantic Escape, Indoor Heated Pool, Hot tub, Breakfast, Art Studio
- Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
- Vintage Chipley Getaway on Large Private Property
- Relaxing in Nature Retreat - Indoor heated pool, Spa, Art Studio, 5-star Bkfst.
- Cozy Lakefront Airstream
- 24 Mi to Morrison Springs County Park: Cozy Home
Which holiday homes in Chipley are best for families?
If you're searching for a family-friendly holiday home in Chipley, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chipley:
How many Casai.co.za holiday rentals are available in Chipley?
As of 2026, Casai boasts over 36 properties listed in the Chipley area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chipley.
