Vacation rentals with a pool in Wealden District

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wealden District

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Icklesham

4.97 out of 5 average rating, 195 reviews

Blackthorn is a luxurious, rural retreat for two.

Blackthorn is a luxurious retreat for two. Attached to the owner's home, and situated on the edge of Icklesham village, the property lies halfway between the ancient towns of Rye and Hastings. There is a distant view of the sea, and the garden is surrounded by beautiful AONB countryside. The cottage has a private, south facing verandah, and guests are welcome to use the heated, indoor swimming pool and outdoor hot tub throughout their stay but exclusively between the hours of 8.00am and 8.00pm.

Feb 28 – Mar 7

G$41,304 GYD per night

Guest favorite

Home in Newington

4.87 out of 5 average rating, 168 reviews

Spacious cosy Barn ideal for exploring Kent

Nunfield Barn is a beautifully converted barn and one portion of the house is internally separated for our Airbnb guests, with its own entrance, downstairs toilet, kitchen/dining area and living room with doors leading to a private patio. Upstairs there are two double bedrooms and a bathroom with bath and shower. There is an above ground pool for use in summer, a front garden shared with us when we are here. There are fields &orchards across the road and we are 15 minute drive to Leeds Castle

Oct 25 – Nov 1

G$30,357 GYD per night

Guest favorite

Guesthouse in Hastings

4.9 out of 5 average rating, 202 reviews

Bright & Spacious Holiday Home With WiFi And GCH

Rorys Village No. 9 Our spacious and clean caravan is situated at Combe Haven in Hastings. It is in a perfect location on site, very close to the amenities but still in a quieter area of the park. With plenty to do on site, including indoor/outdoor pools with bowl flume, ‘Live Lounge’ which hosts a variety of shows for all the family, arcade, ‘Nature Rockz’, ‘Airspace’ sportsdrome which hosts various activities from wall climbing & archery to roller disco plus lots of exciting play areas.

Sep 26 – Oct 3

G$19,307 GYD per night

Guest favorite

Camper/RV in Hastings

4.88 out of 5 average rating, 135 reviews

Prestige 8 Berth Caravan Combe Haven, Hastings (A)

Combe Haven is one of Havens flagship sites boasting an indoor and seasonal outdoor pool, footgolf course, nature reserve, sports bar, Playground, Air Drome activities centre, Launderette and much more. Within the entertainment complex there is an arcade appealing to all ages. The “Live Lounge”, which is your main entertainment venue for the evenings and also the “Mash & Barrel” restaurant. Site facilities, restaurants and Play Passes are managed and subject to availability by Haven.

Jan 20 – 27

G$22,097 GYD per night

Guest favorite

Guesthouse in East Sussex

4.88 out of 5 average rating, 145 reviews

Oast Park Lodge,Idylic,tranquil ,dog friendly

We offer a secluded self catering B&B. Provisions are supplied to allow you total freedom . The accommodation is detached & set in 13 acres of private grounds in a rare pocket of tranquil countryside.Large pool and tennis court. We welcome dogs and have two ourselves..We do impose an extra cleaning charge of £30.00 per animal per stay.This charge will not be collected by Airbnb but should be paid on arrival. There are two great local pubs within easy off-road walking distance.

Oct 17 – 24

G$48,748 GYD per night

Guest favorite

Place to stay in Tunbridge Wells

4.84 out of 5 average rating, 205 reviews

Poole Cottage, retreat near London and the coast.

Pool Cottage is a trendy little place, perfect for couples.Pool is attached to the cottage and guests are welcome to swim any time. Cottage is attached to 16th century Farm House but has a separate gate and private entrance and garden, independent from the house. Rural yet close to main town, London, beautiful Kent and Sussex country side and the coast. Lots of walks and great pubs within walking distance. We also have dogs and bees, country life!

Jun 9 – 16

G$24,608 GYD per night

Guest favorite

Tiny home in Hurstpierpoint

4.97 out of 5 average rating, 284 reviews

Foxhole Escape - The Stable

***Please note this accommodation does not have a hot tub*** Recently renovated stable to accommodate two guest looking for a quiet space over looking a beautiful shared garden and views of the South Downs. Consisting of a cosy dining area and wet room to the ground floor and a double bed and storage on the mezzanine floor. Internet enabled tv and WiFi is available if you need to keep in touch or take in the varied woodland walks that surround if not!

Jan 22 – 29

G$14,411 GYD per night

Guest favorite

Cottage in Rotherfield

4.98 out of 5 average rating, 241 reviews

The Granary at Coes Vineyard, East Sussex

Coes Farm offers 50 acres of absolute tranquillity in amongst nature, with a bit of luxury thrown in too! We have formal gardens and ornamental ponds, a large lake, plenty of woodland, open fields, an indoor saltwater swimming pool with hot tub, a tennis court and a games room which is resident in our Micro-Winery! We planted our 5 acre vineyard in Spring 2021 and extended the existing Orchard with cider varieties in 2023.

Jan 3 – 10

G$49,633 GYD per night

Guest favorite

Vacation home in East Sussex

4.99 out of 5 average rating, 307 reviews

Sea View Holiday Flat + Pool & Spa in Countryside

Luxury studio flat with a spectacular view of the sea and countryside. New: Large private balcony to sunbathe and dine outside. Heated indoor swimming pool, steam room, gym, and outdoor hot tub. King size bed with en-suite, suitable for 2 people. Free high speed wifi throughout. Large smart TV with 200 satellite channels and free Netflix. Located in Hastings Country Park Nature Reserve, short walk to beach.

Dec 13 – 20

G$17,401 GYD per night

Guest favorite

Barn in Battle

4.98 out of 5 average rating, 191 reviews

➡️ The Barn House ⬅️ Swimming Pond▫️Jacuzzi▫️Chicks!

2+ acres of outside space including a natural swimming pond, hot tub, seating areas, BBQ, hammocks, swing chairs, a couple of kid friendly dens to find and a family of chickens. Please help yourself to eggs for breakfast. • Fully equipped + stocked kitchen • Onsite, secured parking for several vehicles • Hot tub and Swimming Pond • Separate games room • Log burner in living room

Dec 10 – 17

G$127,957 GYD per night

Guest favorite

Home in Brighton

4.96 out of 5 average rating, 465 reviews

The House in the Lane

Spacious detached home, with south facing garden and swimming pool in a quiet private residential lane, with a rural feel, yet close to the city centre. Pool optional April and Oct (fee), closed Nov through Mar. No young mixed groups, no team build events, no parties. Families always welcome! Parking (4 cars) 40% monthly discount only for Jan/Feb/Mar.

Jun 14 – 21

G$113,987 GYD per night

Guest favorite

Guesthouse in Rudgwick

4.94 out of 5 average rating, 214 reviews

Bucks Green Place Beautiful Converted Barn

A recently converted barn finished to a very high standard set in the grounds of a Grade II Georgian country house. Situated in idyllic Sussex countryside, nestled close to the Surrey Hills and South Downs. With stunning views across seven acres of garden and open pastures.

Dec 22 – 29

G$20,204 GYD per night