Holiday houses in Headley

Find and book unique accommodation on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated holiday rentals in Headley

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Yarmouth

5 out of 5 average rating, 189 reviews

Sea Drift - a beautiful Fisherman’s Cottage

ChrisRating, 5 stars4 months ago
This a real gem, perfect for exploring the Isle of Wight. The property is tucked away in a quiet mews only 2 minutes from the town centre. The house was immaculate upon arrival and Susan the host had left some nice touches like the bottle of Prosecco in the fridge, as well as other treats. Very comfortable beds and a decent shower which was nice. Lovely spacious downstairs accommodation and nice comfy sofas in the lounge. Outside is a real sun trap ideal for eating al fresco or just sunbathing. The host Susan was very helpful and always responded quickly. A great find, and highly recommended!
Guest favourite

Home in Cowes

4.94 out of 5 average rating, 214 reviews

Seaside villa quiet spot great Sunsets. EV Charger

JoeRating, 5 stars1 week ago
Very nice place to stay, has everything you could need and hosts are cooperative. I would highly recommend if you’re staying in the area.
Guest favourite

Bungalow in Warsash

4.92 out of 5 average rating, 156 reviews

Panoramic Sea Views, quiet, relaxed, Cozy, Beach

MilanRating, 5 stars1 month ago
I had lovely stay at this cool two bedroom bungalow. Beautifully positioned with great views and thoughtfully equipped for a comfortable visit. Would happily return!
Guest favourite

Home in Seaview

4.9 out of 5 average rating, 30 reviews

Stunning 5 Bedroom House

Anna-LouiseRating, 5 stars4 weeks ago
Thank you so much for having us in your lovely home. The house is absolutely beautiful. Furnished with such pretty things, full of little personal touches - toys for kids, lovely toiletries, radios in all the rooms. Pandora was super responsive and helped us find lots of fun local activities for the kids - it honestly felt like a home away from home and we’ll definitely put it up there with one of the best Air BnBs we’ve stayed in. Thanks again for having us! We’d love to return in summier climes!
Superhost

Apartment in Hackney

4.7 out of 5 average rating, 79 reviews

3/4-bed flat in the heart of Broadway Market

HilleryRating, 5 stars2 weeks ago
We really enjoyed our stay at Rich’s apartment! Great little place in an unbeatable location. Opens up right onto Broadway market where there are so many options for snacks and shopping! Very close to public transportation as well. Tile floors throughout so bring your slippers!
Guest favourite

Townhouse in Ocean Village

4.94 out of 5 average rating, 158 reviews

Romantic Couples Getaway with a Hot Tub

MattRating, 5 stars1 month ago
Booked this place for my wife's birthday and it was amazing all down to the last detail! The apartment is just as it looks in the pictures with lots to do and fun to be had! Enjoyed the hot tub area which was really nicely done! The goody bag left by the host was a really nice touch! Oxford street is opposite with plenty of restaurants and cocktail bars so the location is perfect! Would really recommend for anyone wanting to get away for a romantic night or two!
Guest favourite

Apartment in Hampshire

4.93 out of 5 average rating, 321 reviews

Luxurious rooftop terrace modern apartment xxxxxx

TomRating, 5 stars3 weeks ago
We had a very enjoyable stay. The place was very clean, modern and easy to access. The bathrooms were some of the nicest we've had in b&b's. Excellent shower. Great bedrooms with tv's on the wall. Felt like a really well maintained apartment.
Guest favourite

Condo in Seven Dials

4.9 out of 5 average rating, 194 reviews

One bed basement flat with Patio centrally located

NdoRating, 5 stars1 week ago
Lovely flat. Clean and comfortable. Really great location and Alan was very helpful. Would definitely recommend.
Superhost

Apartment in The City of Brighton and Hove

4.88 out of 5 average rating, 598 reviews

Charming Balcony Flat <--200m from Beach

TessRating, 5 stars4 weeks ago
Great location to explore Brighton. good kitchen and living space. No door to the bedroom (around the corner of the livingroom), good to know when travelling with a baby. Baby bed was available, very convenient for us. All in all a good space to spend a couple of days.
Guest favourite

Chalet in Yaverland

4.89 out of 5 average rating, 105 reviews

2 bed chalet near the beach and tiger sanctuary

CorinneRating, 5 stars4 months ago
I will highly recommend this place. Very clean with everything you need in the kitchen. Close to many beaches, walks, and loads of attractions around for adults and children. Our host was very responsive to any e-mails we sent her. We will definitaly come back. Thank you again for having us in your chalet. Corinne & Chay
Guest favourite

Guesthouse in East Wellow

5 out of 5 average rating, 30 reviews

Lake View Cottage

LeeRating, 5 stars2 months ago
Amazing place for a retreat from the city, absolutely gorgeous place and location. The hot tub was fantastic and it's autumn so the leaves from tress created a beautiful scene! Would love to come back and take time out from the city! Lovely villages close by with friendly people if you want to venture further afield.
Guest favourite

Cottage in Brading

4.95 out of 5 average rating, 150 reviews

Marmalade Cottage 5* Scenery, Beach, AONB Location

DaveRating, 5 stars3 months ago
Julie was extremely helpful and communicative, giving us both the privacy we required but also available for anything we needed. She seemed genuinely invested in us having the best break possible. Beautiful little touches around the house and perfect size/facilities for our family. A very short distance to a great beach with lots to do around that area, but also on easy routes to travel around the island. Thank you both very much. We hope to come back, but next time for longer!

Popular amenities for Headley holiday rentals

Stay near Headley's top sights

The Crown at Arford6 locals recommend
The Royal Exchange5 locals recommend
Headley Fine Foods3 locals recommend

Other great holiday rentals in Headley

Guest favourite

Condo in Isle of Wight

5 out of 5 average rating, 129 reviews

Osborne Cottage, Royal Estate, Luxury Apartment

KirstyRating, 5 stars4 months ago
Fabulous apartment, very comfortable and with an amazing garden and views. Felt like home away from home and Richard was one of the best hosts I have encountered in airbnb. Would highly recommend staying here
Guest favourite

Home in Hampshire

4.96 out of 5 average rating, 25 reviews

Detached Seaside Bungalow in Quiet Cul De Sac

LorettaRating, 5 stars3 months ago
James was good at communicating, and left clear instructions for everything. He also met us on arrival. The bungalow was as per the description and photos (please note that bed 3-twin room has drawer clothes storage but no hanging space). It's clean, light and airy. The bungalow was in a quiet location and yet close to amenities and a short walk to the beach. We had 3 cars between us and were easily able to fit them on the driveway. We would happily return!" I can't think of anything else that any potential guest would need to know above the information on Airbnb and reviews already left.
Guest favourite

Home in West Sussex

5 out of 5 average rating, 22 reviews

Beautiful Bramber Fox.

HelenRating, 5 stars2 months ago
We had a lovely stay, we were a group of old friends and needed a place we could sit comfortably and chat and catch up. The house was a very social space and extremely well equipped. The beds were comfy and the bathrooms had great showers and plenty of hot water. Lovely hot tub too! Friendly helpful hosts and couldn’t find a thing to complain about. I would recommend without any hesitation.
Guest favourite

Condo in Gunwharf Quays

4.84 out of 5 average rating, 103 reviews

Newly Renovated Self Contained Studio with Parking

HonoreRating, 5 stars1 month ago
Perfect for a week's stay - close to public transport and great shopping area, would recommend!
Guest favourite

Home in Haywards Heath

4.95 out of 5 average rating, 19 reviews

The Barn at Stoaches - Country retreat with a pool

MichelleRating, 5 stars2 months ago
We had a fantastic stay at the barn this November. Michelle was a great communicator for any questions I had which made the whole process effortless. The owners are lovely and the barn exactly as described. Hoping to return in the Summer to be able to take advantage of the pool.
Guest favourite

Barn in Isle of Wight

5 out of 5 average rating, 210 reviews

Stargazer Cottage with a private hot tub

CarolineRating, 5 stars4 days ago
We had a wonderful weekend at the Stargazer Cottage surrounded by stunning countryside. It was so peaceful and has beautiful surroundings. Nicola was incredibly helpful and friendly, went the extra mile to make it such a lovely stay for us. The cottage matches the photos and would highly recommend for anyone needing a relaxing getaway! Can’t wait to come back again!
Guest favourite

Tiny home in West Meon

4.92 out of 5 average rating, 180 reviews

Cosy cabin in Annie’s meadow

KamilRating, 5 stars4 days ago
Lovely place to stay! Very peaceful and beautiful surroundings! Would definitely recommend!
Superhost

Apartment in Greenwich

4.78 out of 5 average rating, 18 reviews

Spacious 2 bed near O2/ Riverwalk/ecology park

AmarRating, 5 stars2 months ago
Excellent place and neighborhood. It is definitely a home away from home. I am a long term guest and this is a place I will return to again next year. Thanks to Aza for being a wonderful host.

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Headley