94+ Private Villas and Holiday Rentals in Headley |
Headley Holiday Rentals
10.0
Exceptional
(49 Reviews)
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R6,076/Night
For 7 Nights R42,539
9.6
Exceptional
(16 Reviews)
398.26 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Breakfast
- Parking
R1,718/Night
For 7 Nights R12,024
10.0
Exceptional
(1 Review)
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Internet
R5,502/Night
For 7 Nights R38,514
9.6
Exceptional
(7 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Parking
- Air Conditioner
- Internet
R2,403/Night
For 7 Nights R16,824
10.0
Exceptional
(1 Review)
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R4,134/Night
For 7 Nights R28,949
10.0
Exceptional
(1 Review)
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R2,484/Night
For 7 Nights R17,396
6.0
Good
(1 Review)
370 ft²
3 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Internet
- Child Friendly
R3,015/Night
For 7 Nights R21,101
New
18 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R47,270/Night
For 7 Nights R330,896
Luxury Holiday Rentals in Headley
Over 85+ Luxury Holiday Rentals in or Near Headley
New
538.2 ft²
15 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- View
- Parking
R29,345/Night
For 7 Nights R205,419
New
9999.67 ft²
18 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
Villa
- Hot Tub
- Balcony/Terrace
- View
R27,974/Night
For 7 Nights R195,820
New
6771 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R17,661/Night
For 7 Nights R123,625
9.4
Exceptional
(54 Reviews)
- United Kingdom
- Box Hill
- 1.53 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Spa
- Pool
R11,280/Night
For 7 Nights R78,964
New
- England
- Betchworth
- 1.19 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Kitchen
- Parking
- Internet
R10,553/Night
For 7 Nights R73,862
9.0
Exceptional
(1 Review)
2497.23 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Breakfast
- Kitchen
R7,982/Night
For 7 Nights R55,876
New
4 Guests
2 Bedrooms
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Child Friendly
- Laundry
R6,118/Night
For 7 Nights R42,825
New
- England
- Leatherhead
- 2.52 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Parking
- Internet
- Child Friendly
R5,651/Night
For 7 Nights R39,558
New
- England
- Leatherhead
- 2.52 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Parking
- Internet
- Child Friendly
R5,651/Night
For 7 Nights R39,558
Top-Rated Holiday Rentals with a Pool in Headley
Over 4+ The Best Private Villas and Holiday Rentals in Headley with a Pool
8.2
Excellent
(690 Reviews)
- United Kingdom
- Box Hill
- 0.58 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
R1,306/Night
For 7 Nights R9,144
7.9
Very Good
(23 Reviews)
- United Kingdom
- Box Hill
- 0.57 mi to center
199.13 ft²
2 Bathrooms
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- View
R3,559/Night
For 7 Nights R24,907
7.6
Very Good
(1388 Reviews)
- United Kingdom
- Box Hill
- 0.58 mi to center
252.96 ft²
4 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,699/Night
For 7 Nights R18,895
2.0
Average
(2 Reviews)
- United Kingdom
- Box Hill
- 0.57 mi to center
237 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Balcony/Terrace
- Pet Friendly
R2,704/Night
For 7 Nights R18,929
Pet-Friendly Holiday Rentals in Headley
Over 10+ Pet-Friendly Holiday Rentals in or Near Headley
3.3
Average
(7 Reviews)
10000 ft²
22 Guests
8 Bedrooms
8 Bathrooms
Family Friendly
House
- Pet Friendly
- Kitchen
- Laundry
R22,617/Night
For 7 Nights R158,316
9.5
Exceptional
(6 Reviews)
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Balcony/Terrace
- View
- Pet Friendly
R2,952/Night
For 7 Nights R20,663
New
1 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Pet Friendly
- Kitchen
- Laundry
R6,433/Night
For 7 Nights R45,031
New
- England
- Leatherhead
- 2.91 mi to center
818 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R5,117/Night
For 7 Nights R35,819
8.0
Excellent
(1 Review)
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
R2,453/Night
For 7 Nights R17,177
New
- England
- Leatherhead
- 2.83 mi to center
807 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R4,657/Night
For 7 Nights R32,603
8.5
Fabulous
(396 Reviews)
193.75 ft²
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R2,484/Night
For 7 Nights R17,396
8.3
Excellent
(535 Reviews)
- England
- Betchworth
- 0.70 mi to center
118.4 ft²
10 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
R1,953/Night
For 7 Nights R13,674
Large Holiday Rentals and Private Villas in Headley
Over 3+ Large Holiday Rentals and Private Villas in or Near Headley
9.0
Exceptional
(2 Reviews)
8999 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R33,075/Night
For 7 Nights R231,521
9.5
Exceptional
(42 Reviews)
- England
- Leatherhead
- 2.37 mi to center
538.2 ft²
16 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Internet
- Child Friendly
R2,317/Night
For 7 Nights R16,217
4.0
Average
(1 Review)
8 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R4,853/Night
For 7 Nights R33,967
Wheelchair Accessible Holiday Homes in Headley
Over 8+ Wheelchair Accessible Holiday Homes in or Near Headley
New
- England
- Leatherhead
- 2.73 mi to center
872 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R5,170/Night
For 7 Nights R36,190
9.0
Exceptional
(1358 Reviews)
335.48 ft²
6 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
R2,830/Night
For 7 Nights R19,804
9.4
Exceptional
(209 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
R3,014/Night
For 7 Nights R21,101
New
- England
- Leatherhead
- 2.70 mi to center
785 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R4,885/Night
For 7 Nights R34,186
8.5
Fabulous
(1683 Reviews)
204.51 ft²
3 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Parking
- Air Conditioner
R1,978/Night
For 7 Nights R13,843
9.0
Exceptional
(983 Reviews)
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Breakfast
- Kitchen
R1,950/Night
For 7 Nights R13,641
8.5
Fabulous
(588 Reviews)
- England
- Betchworth
- 0.67 mi to center
150.7 ft²
8 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
R3,600/Night
For 7 Nights R25,210
New
- England
- Leatherhead
- 2.45 mi to center
1 Bathroom
Family Friendly
Hotel
- Pet Friendly
- Parking
- Child Friendly
R1,200/Night
For 7 Nights R8,403
Headley Private Villas and Holiday Homes Under $200
Over 22+ Headley Private Villas and Holiday Homes Under $200
9.0
Exceptional
(2 Reviews)
- England
- Leatherhead
- 2.79 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
R2,763/Night
For 7 Nights R19,350
9.2
Exceptional
(11 Reviews)
548.96 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Internet
R2,728/Night
For 7 Nights R19,097
9.2
Exceptional
(183 Reviews)
1 Bathroom
Couples Retreat
Hotel
- Balcony/Terrace
- Breakfast
- Internet
R2,166/Night
For 7 Nights R15,156
5.0
Average
(1 Review)
- England
- Leatherhead
- 2.29 mi to center
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Child Friendly
R2,804/Night
For 7 Nights R19,636
8.0
Excellent
(1 Review)
441.32 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Parking
- Internet
R2,189/Night
For 7 Nights R15,325
1.0
Average
(1 Review)
- England
- Leatherhead
- 2.38 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Child Friendly
R3,104/Night
For 7 Nights R21,724
New
- England
- Leatherhead
- 2.50 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Internet
- Child Friendly
R2,854/Night
For 7 Nights R19,973
New
- Leatherhead
- Fetcham
- 0.85 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Internet
R2,188/Night
For 7 Nights R15,325
New
- England
- Leatherhead
- 2.44 mi to center
495 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Child Friendly
- Security/Safety
R3,304/Night
For 7 Nights R23,122
Instantly Bookable Holiday Homes in Headley
Over 24+ Instantly Bookable Holiday Homes in or Near Headley
New
- England
- Betchworth
- 0.86 mi to center
1130 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
R4,672/Night
For 7 Nights R32,704
5.0
Average
(1 Review)
- England
- Leatherhead
- 2.32 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Child Friendly
R3,924/Night
For 7 Nights R27,467
New
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Child Friendly
- Bedding/Linens
- Security/Safety
R8,625/Night
For 7 Nights R60,373
New
2000 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Internet
R8,088/Night
For 7 Nights R56,617
New
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R5,028/Night
For 7 Nights R35,196
New
- England
- Leatherhead
- 2.41 mi to center
667 ft²
2 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Child Friendly
- Security/Safety
R4,504/Night
For 7 Nights R31,525
New
- England
- Leatherhead
- 2.57 mi to center
839 ft²
2 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Child Friendly
- Security/Safety
R4,329/Night
For 7 Nights R30,296
New
- England
- Leatherhead
- 2.42 mi to center
915 ft²
2 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Child Friendly
- Security/Safety
R4,259/Night
For 7 Nights R29,807
New
- England
- Leatherhead
- 2.24 mi to center
667 ft²
2 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Internet
- Child Friendly
- Security/Safety
R4,194/Night
For 7 Nights R29,353
Book a Last Minute Place to Stay in Headley
About Casai's Private Villas and Holiday Rentals in Headley
Discover more than 94 vacation rentals available in Headley. 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 Headley.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Headley, 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 Headley. On average, places to stay near Headley offer 1318.37 ft², with nightly prices averaging R5,536.
With Casai, finding and comparing holiday rentals in Headley is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Headley
| Type | Count |
|---|---|
| Holiday Apartments | 61 |
| Vacation Homes | 12 |
| Cottages | 3 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Headley
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Headley.
Weather in Headley, GB
View the weather forecast for Headley before booking your Headley Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 32°F
March - May
High 61°F Low 36°F
June - August
High 63°F Low 48°F
September - November
High 58°F Low 35°F
Frequently Asked Questions About Headley?
What are the top holiday rentals in Headley?
With numerous options available in Headley, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Headley:
- Beautiful Victorian cottage in Ashtead easy access to London set in countryside
- Modern Serenity in Langley Vale
- Cozy Maisonette in Langley Vale
- Newly renovated flat in Ahsteadnn
- Westleigh
- Comfy Apartment 16 Easy access to Central London
- Highway Cottage - Mickleham
- Roomspace Serviced Apartments - Swan House
- Cozy Maisonette in Langley Vale
- The Lodge at Kingswood
Which holiday homes in Headley are best for families?
If you're searching for a family-friendly holiday home in Headley, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Headley:
How many Casai.co.za holiday rentals are available in Headley?
As of 2026, Casai boasts over 94 properties listed in the Headley area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Headley.
People Also Ask
Finding the best prices in Headley
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