
Holiday rentals with a pool in Weymouth and Portland District
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Top-rated rentals with a pool in Weymouth and Portland District
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Country House - Pool Jacuzzi Escape Room Karaoke
Group Gatherings Host your own event Exclusive use 10-16 guests Min 2 off peak Jacuzzi All year Outdoor Pool (heated in summer; cold in winter!) Sun Deck Garden Kitchen/Bar Games room: Music/Karaoke system Wood burner TV Communal eating space, shower/wc Escape Room Somerset Evening -pulled pork cider tasting welly wanging Large peaceful grounds BBQ Fire Pit Annexe (sole use) kitchen lounge bathroom 2 bedrooms 2 sofa beds House (part use): 4 bedrooms 3 bathrooms Glamping Trailer

Shepherd's Hut (wood-fired hot tub/sauna optional)
Get away from it all and create romantic memorable moments in your rustic Acorn Hut. Step outside and be enveloped by nature and enjoy sitting in front of a fire pit or have a BBQ or a relaxing hot tub (EXTRA CHARGE). Acorn Hut has everything you need to stay comfortably and is particularly suited for nature lovers. Its small Hobbit wood burner will keep you snug and warm on a cold evening. Toilet/shower. Other cabins on site/ Horton Road which can be noisy at times. Hut is not fully fenced in.

Everdene shepherd's hut
Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

Summer Lodge
The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

Buzzard Yurt - A unique eco holiday in East Devon
Unique and comfortable yurt (sleeps 5+), large terrace, stunning views - also you could check out Kingfisher yurt (bigger kitchen) by the swimming pond. Private kitchen, chill-out cabin, shower, rustic flushing loo, compost loo with a view, campfire area. Wild swimming pond (fenced) Hot tub (can be advance booked by EITHER Kingfisher or Buzzard yurt). Dog friendly, footpaths. Kid heaven! By booking you take responsibility for safety of your group. Check-in form /waiver on arrival please.

Big 3 bed cottage with wild swimming & woodburner
The Stables at Combe Head House are nestled within the private grounds, tucked away from the road. Enjoy our meticulously renovated three-bedroom converted stables. Decorated with a curated selection of vintage furniture, this enchanting space offers a unique blend of old-world charm and modern comfort. Plenty of parking right outside on a large private driveway. Escape the hustle everyday life and immerse yourself in the timeless beauty of our historic stables. Time to relax and recharge…

A luxury unique home spa - White Stones Retreats.
Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

A luxurious modern 3-bedroom Swift Bordeaux
A luxurious modern 3-bedroom Swift Bordeaux Silver Prestige. This fabulous caravan is situated at Haven Littlesea Holiday Park in Weymouth in a spacious plot with views of the Fleet Lagoon and Chesil Beach. Sleeps up to 6 people. 1.5 bathrooms Linen and towels supplied. Parking spaces for 2 cars. Outside decking and seating area. Onsite restaurant, laundrette and local shop. For use of swimming pool, entertainment venue and booking activities you can purchase Play Passes from Haven

Luxurious holiday home at Weymouth Bay
2015 Luxurious Willerby Chambery static holiday home. Located in a quiet corner on Havens Weymouth Bay Holiday Park. Sleeps 4/up to 6 if using sofa bed. 2 Bedrooms. Sorry no pets.The main bedroom en suite toilet and sink and 24” smart tv/ dvd. 1 x twin bedroom and a pull out sofa bed in lounge. 43” smart tv player in lounge. Wi-fi , Bluetooth speakers in ceiling. Full size fridge/freezer, microwave, full size cooker. Central heating and double glazing. Patio doors, decking.Allocated parking

Stunning Barn conversion with heated swimming pool
Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

Foxglove Carriage with pool, sauna & outdoor bath
Nestled into our working farm, this lovingly restored railway carriage is the perfect spot for a romantic stay away. The views are out of this world and all viewable from the large glass doors so you can stay tucked up in bed or on the sofa in front of the fire, with great wifi, free access to our beautiful heated pool and sauna in the pool house, beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and romantic outdoor bath.

Piilopirtti - a traditional Finnish log cabin
Spend your days in a traditional Finnish log cabin with a grass roof. Step outside and be enveloped by rhododendrons and enjoy sitting in front of a fire pit or a BBQ amongst trees and nature. The main room is for sleeping and living with a super-king size bed, table, TV, 2 easy chairs. The cabin has a fully equipped kitchen and a bathroom. Cabin is not fenced in. Adjacent to Ringwood Forest where you will find a cycle trail, Moors Valley Country Park, a golf course and a lake.
Popular amenities for Weymouth and Portland District rentals with a pool
House rentals with a pool

Woodcutter's Cottage

Launceston Farmhouse with swimming pool & sauna

Susie's Caravan in Dorset

Fontwood Cottage – Woodland Hideaway with Hot Tub

Spacious Caravan near sea Weymouth Bay Haven

Heated Pool, Hot Tub, Sauna, Games - Upton Bourn

East Creek, beach, pool, dog, hot tub - Ringstead

The Old Shop at Durdle Door
Apartment rentals with a pool

The Palms, Apartment 20

Seascape Apartment

Holiday apartment own heated indoor pool & sauna

Apartment 12

Flat 10 Pelican House

Bournemouth Apartment 23

The Palms Apartment 16 with Balcony

Bournemouth 2 Bedroom Apartment 22
Other holiday rentals with a pool

Littlesea Holiday Park - High Spec ‘Silver’ Van

Modern Spacious Holiday Home With Sea Views

Chesil View

Cosy Cabin in the New Forest at Sandy Balls

5star Beachside Park & Spa | Jurassic Coast Luxury

Log Cabin with Private Hot Tub in The New Forest

Our Plaice by the Sea

2 Haven - studio/sea views/indoor pool/steam room
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- New Forest National Park
- Bournemouth Beach
- Weymouth Beach
- Paultons Park Home of Peppa Pig World
- Stonehenge
- Longleat Safari Park
- Southbourne Beach
- Boscombe Beach
- Mudeford Quay
- Brixham Harbour
- Lyme Regis Beach
- The Tank Museum
- Torquay Beach
- Durdle Door Holiday Park
- Kimmeridge Bay
- Beer Beach
- Bournemouth International Centre
- Crealy Theme Park & Resort
- Highcliffe Beach
- West Bay Beach
- Powderham Castle
- Hoburne Naish Holiday Park
- University of Exeter
- Stourhead





