
Vacation 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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Headland Hideaway Shepherd's Hut in Lyme Regis
SHEPHERDS HUT An opulent hideaway retreat nestled on the Lyme Bay headland with uninterrupted ocean views, perfect for romantics & family adventurers. With an expansive sundeck, fire pit & swimming pool & endless expanse of garden. Embark on the most charming private adventure from bedroom shepherd's hut & adjacent shower room to the architectural wonder of the glass framed kitchen, diner & sitting room with freestanding log burner & stylish interior. Sit and wonder at the expanse of ocean views

Cosy Shepherd's Hut with wood-fired hot tub
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 are only a few meters away. One photo shows its location to other cabins / Horton Road.

Kingfisher yurt, A unique eco holiday in Devon
Unique yurt (sleeps 5+) surrounded by oak trees, next to the wild swimming pond (shared /gated.) Also check out Buzzard yurt with its terrace / views Private large, rustic, open plan kitchen (+ games, maps and books), shower, compost loo and fire pit. The shared games/music cabin adjoins your kitchen. Dog friendly. Use of our 26 acre rewilding woodland a 45 minute hike away. Bookable hot tub. The safety of your group is your responsibility. Check-in form /waiver to sign on arrival please.

Family friendly & comfortable 2 Bed Holiday Home
Family friendly 2-bed holiday home (sleeps 6), centrally heated & double glazed throughout. Located in a quiet cul-de-sac close to all park amenities & adjoining beach. Price includes Wi-Fi. Open plan living space with large L shaped sofa/bed, 43" TV, & fully equipped integrated kitchen. Family shower room, & an en-suite to the Master bedroom, which also has a fitted double wardrobe, 32” TV & king-size bed. The twin bedroom has two single beds. The patio doors lead to a wraparound veranda.

Secluded hideaway, heated pool, walks, fossils
The Annex is bright, comfortable and cosy with a wood burner for winter. The public footpath crossing our garden next to the river Char links with many others - great for dog walkers. We are close to Charmouth beach and Lyme Regis – renowned for their fossil treasures. Love swimming? our freshwater pool is generally heated to a very cosy 29 - 30 degrees (warm bath temperature) and can be used from April to October With advance notice, the twin beds can be connected to form a king size bed

Clover Carriage with pool, sauna and 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 heate pool & sauna (located in the pool house), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and a romantic outdoor bath

Breathtaking sea views from this light, cosy lodge
Seascape is a bright, airy lodge down its own drive at the edge of Swanage Bay View. Adjoining Townsend Nature Reserve it enjoys utter tranquillity and spectacular views over the bay, as seen on 'A Place in the Sun'. With its tasteful modern furnishings, central heating and double glazing, Seascape is cosy in winter, while outside, the large deck offers a panoramic view all the way to Corfe Castle. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

Get-a-Wey a static caravan at Haven Weymouth Bay
SUPERB ' 2020' edition ABI New Horizon. Sleeps up to 8 people. 1 double, 2 twin bedrooms (pull-out double sofa bed in lounge), shower/toilet, separate toilet, kitchen and lounge area. Located in a quiet area of the park and a short walk to nearby Bowleaze Cove. Note; This is caravan ONLY, a Haven pass may be required to access some areas of the park, including swimming pools. Prices for passes can be found on Haven website. WiFi is available throughout the caravan and main buildings

Spacious Caravan near sea Weymouth Bay Haven
Our holiday home is spacious with a well equipped kitchen. Located 12-15min flat walk (buggy friendly) from the seaside. The Haven park offers a swimming pool, live entertainment and play areas for kids until 14th November (access to indoor complex is an additional fee on a first come first serve basis) We are opposite the activity field. One car parking space next to the caravan.. CHANGEOVER DAYS ARE MONDAY OR FRIDAY. Please contact us to make a shorter booking or with any questions.

Daisy Cottage on the Jurassic Coast
A cosy and stylish, dog-friendly cottage, set amid the beautiful fields and woodlands of the Fernhill Estate with easy walking access to the coastal village of Charmouth and only 2 miles to Lyme Regis. The South West Coastal Path runs opposite our front door and our guests have seasonal access to a heated outdoor pool. Our cottage sleeps four and is furnished and equipped to a very high standard with everything you need for a relaxing holiday on the Jurassic Coast in West Dorset.

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.

The Duck House. A child/dog friendly rural chalet
The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.
Popular amenities for Weymouth and Portland District rentals with a pool
House rentals with a pool

Your Own Private Indoor Pool. Rural Seaside

Country House - Pool Jacuzzi Escape Room Karaoke

Large Airy Barn conversion, 5 bedrooms, Jurassic

Pet friendly 2 bed holiday home

5-Bedroom Retreat w/ Pool, Sauna, Garden & Bar

Peaceful West Dorset location

Gamekeeper's Cottage

Acorn House
Condo rentals with a pool

Seascape Apartment

Holiday apartment own heated indoor pool & sauna

Apartment 12

The Palms Apartment 16 with Balcony

2-BR Penthouse Apt. close to Beach with Pool*.

The Palms, Apartment 19

The Palms Studio 6

Modern one bed flat with sauna
Other vacation rentals with a pool

Bay View Holiday Home With Sea Views

Cosy caravan in private woodland setting

Sleeps 6 with wild swimming & woodburner

A homely seaside static caravan

Amazing Lodge, edge of Forest with giant deck

Kingfisher Lodge with Sea Views

1 Haven - studio/sea views/indoor pool/steam room

Our Plaice by the Sea
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- New Forest national park
- Bournemouth Beach
- Weymouth Beach
- Paultons Park Home of Peppa Pig World
- Stonehenge
- Boscombe Beach
- Kimmeridge Bay
- Southbourne Beach
- Highcliffe Beach
- The Tank Museum
- Poole Quay
- Crealy Theme Park & Resort
- Sandy Bay Beach Blue Flag Winner 2019
- Beer Beach
- Preston Sands
- Mudeford Sandbank
- Man O'War Beach
- Charmouth Beach
- Torre Abbey
- Oddicombe Beach
- Hurst Castle
- Elberry Cove
- Compton Beach
- Oake Manor Golf Club