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Family-friendly vacation rentals in Weymouth and Portland District

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Top-rated family-friendly rentals in Weymouth and Portland District

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Cottage in Dorset

4.88 out of 5 average rating, 308 reviews

18th Century Coastal Cottage

This historic home features original stone floors, rustic wood beam ceilings, a wood-burning fireplace, modern finishes, a sauna, and a private back patio overlooking the beach. Breathe in the refreshing ocean air from this hillside retreat. I’m sorry I have a no pets policy at the cottage. This cottage has steep stairs, low ceilings, a very low rise bed and a low sofa as seen in the pictures. 60 Mallams was built in approximately 1760 and still has many rustic features throughout. The cottage has two levels, ground floor consists of open plan lounge leading to the kitchen then conservatory with shower room. Which opens out into courtyard garden with a terrace and sea views. 1st floor has the main bedroom with a super king size bed and separate bathroom with a free standing bath with room for two.. Private parking on driveway 24hr key access safe by the front door I can be contacted at any time throughout your stay. The property is located just a five minute walk from Chesil Beach. It is also close to a number of the town's local shops and cosy pubs. There’s plenty of coastal walks all around Portland The sailing club is close offering various water sports There is bus services to and from Weymouth. There are amazing coastal walks around Portland. Please be mindful of the rubbish I have food waste bins , glass only tubs and the larger of the wheelie bins (green) are recycling only ( cans paper and plastic) and the black bins are general rubbish.. please be careful with the rubbish because if it's all mixed up the bin men won't take it away...

Nov 30 – Dec 7

R4,104 ZAR per night

Apartment in Weymouth

4.92 out of 5 average rating, 117 reviews

Marina Place Weymouth

Marina Place Weymouth Is a modern very good sized 2 bedroom 2nd floor Apartment with wonderful views over inner harbour, & marina, Swannery & bowls green. It’s on the edge of town & a 2 minute walk to the beach & shops Its 5 minutes from Train & Bus Station. It has lift, gated, parking for one vehicle. It has Juliet balconies from the bedrooms & kitchen dinner with great views & large bathroom & also ensuite shower room on main bedroom which makes it idea for families or couples. SORRY NO PETS

Mar 31 – Apr 7

R3,265 ZAR per night

Home in Dorset

4.94 out of 5 average rating, 119 reviews

Blue Bay Cottage - Cove Street, Weymouth Harbour

Beautiful 3 bedroom cottage close to Weymouth harbour and town centre. Own entrance leading to dining room, kitchen, conservatory, cloakroom and rear courtyard. Stairs to lounge with gas stove, bathroom with large shower and single bedroom. Further stairs to master bedroom and twin bedroom. Kitchen with integrated dishwasher, fridge, Neff hide and slide oven, microwave. The cottage has gas central heating and a parking permit for on street/harbourside parking. WiFi and outside space to sit

Mar 6 – 13

R4,254 ZAR per night

Condo in Uplyme, Lyme Regis

4.93 out of 5 average rating, 595 reviews

Idyllic Garden Studio - Couple’s Sanctum - by Sea

Romantic hideaway on the East Devon Way. Luxurious couple’s bath, solid oak sleigh bed with sumptuous pocket sprung mattress, private outside space for dining/sunbathing. Fully equipped for self-catering. Overlooking delightful, tranquil courtyard garden. Perfect place of refuge and relaxation. Ideal base for walking the World Heritage Jurassic Coast or visiting River Cottage. Village centre 5 mins walk with pub, shop, tennis court. Lyme beach 10 mins drive or 45 mins via idyllic river walk.

Aug 26 – Sep 2

R2,766 ZAR per night

Cottage in Winfrith Newburgh

4.98 out of 5 average rating, 251 reviews

Bramble - 17th Century Barn Conv -enclosed garden

Bramble Barn is a beautiful 17th-century barn conversion situated down a private road just 4 miles from Lulworth Cove, Durdle Door and the Jurrasic Coast World Heritage Site. This large splendid brick barn has been converted into two identical properties creating accommodation of the highest standards. Each barn has its own enclosed garden and a south-facing terrace, ideal for eating out. Tadnoll Heath, a Dorset Wildlife Trust Reserve, lies just to the north. Ample off-road parking.

Mar 10 – 17

R3,196 ZAR per night

Guesthouse in Dorchester

4.97 out of 5 average rating, 274 reviews

Lovely, Quiet Studio Annex (with Netflix)

Self contained, self catering studio annex based in the county town of Dorchester. The annex is suitable for 2 adults (a z-bed can be supplied for 1 child under 12). The towns amenities are all within a short walking distance, including the new 'Brewery Square' development. Great base to explore Dorset's fabulous coast, countryside and walk in the footsteps of Thomas Hardy's Casterbridge. Motorbike friendly, high chair & travel cot available. Complimentary tea and coffee. Netflix TV.

Sep 22 – 29

R1,611 ZAR per night

Cottage in Dorset

4.98 out of 5 average rating, 161 reviews

Character cottage with sea views and parking

200-year old 'Quarryman's Cottage' is just a short walk from Chesil Beach and the South West Coast Path and the perfect base for a family holiday in Dorset. It offers a private balcony with stunning sea views, off-road parking, three bedrooms, and open plan dining/living room with log burner. The local area is fantastic for windsurfing, sailing, kitesurfing, paddleboarding, climbing, walking, bird-watching, diving and fishing. We hope you enjoy it as much as we do!

Feb 22 – Mar 1

R4,078 ZAR per night

Cottage in Dorset

4.98 out of 5 average rating, 312 reviews

The Condo (Indoor Pool available May-Oct only)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Jan 18 – 25

R2,417 ZAR per night

Apartment in Weymouth

4.91 out of 5 average rating, 599 reviews

Splendid Quiet Ground Floor Apartment Near the Sea

This gorgeous large studio apartment with separate entrance is contained within an historic Georgian house, minutes from the ocean. Peace and quiet are ensured by a large well tended front garden with off street parking. The accommodation has a spacious shared patio, giving way to an established secluded garden. The apartment boasts a stylish fully fitted kitchen and leather Chesterfield sofa, chairs and a large comfy bed .

Aug 1 – 8

R2,634 ZAR per night

Chalet in Weymouth

4.95 out of 5 average rating, 166 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted and unrivaled views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the Jurassic Coast path. 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.

Jul 20 – 27

R6,311 ZAR per night

Place to stay in Weymouth

4.94 out of 5 average rating, 206 reviews

Pebble Lodge

Pebble Lodge is a stylish, modern and luxury home from home for four guests (plus one infant). Situated on the five star Chesil Beach Holiday Park, Pebble Lodge boasts an uninterrupted view of the Fleet Lagoon and Chesil Beach, infamous parts of the Jurassic Coast. Beautiful accommodation, finished with some personal touches really makes Pebble Lodge the perfect coastal escape in all seasons.

Sep 24 – Oct 1

R4,749 ZAR per night

Condo in Dorset

4.95 out of 5 average rating, 275 reviews

Your hideaway on Weymouth harbourside!

Harbour Hideaway....light and airy basement apartment with own courtyard in fantastic harbourside location. Permit parking for 1 car and dogs welcome. Main sandy beach 5 mins away and town is just across the bridge. Friday changeovers preferred if weekly durations. Please note that there are two single beds in the bedroom and a drop down King Size bed in the lounge (not in a separate room) x

Dec 19 – 26

R3,000 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

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Adventure-ready homes with après-ski style

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Convenient locations with everyday essentials

Popular amenities for Weymouth and Portland District family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Sandleheath

4.96 out of 5 average rating, 222 reviews

Orchard Barn Spa, exclusively for you, New Forest

Nov 22 – 29

R3,664 ZAR per night

Cottage in Dinnington

4.95 out of 5 average rating, 427 reviews

The Cottage, Parsonage Farmhouse with hot tub

Oct 17 – 24

R2,853 ZAR per night

Cottage in Dorchester

4.99 out of 5 average rating, 166 reviews

Charming Brick Cottage with a Patio and Hot Tub

Mar 26 – Apr 2

R5,285 ZAR per night

Shepherd’s hut in Ilminster

5.0 out of 5 average rating, 201 reviews

Romantic Shepherds Hut & Wood-fired Hot Tub

Apr 4 – 11

R3,189 ZAR per night

Cottage in Stockland

4.99 out of 5 average rating, 271 reviews

Blackdown Hills Hot Tub retreat

Dec 19 – 26

R2,700 ZAR per night

Home in Wiltshire

4.97 out of 5 average rating, 218 reviews

Glebe House, a beautiful country home

Mar 26 – Apr 2

R6,668 ZAR per night

Barn in Trull

4.96 out of 5 average rating, 169 reviews

The Apple Press - Sweethay

Apr 6 – 13

R4,450 ZAR per night

Home in Wimborne St Giles

4.93 out of 5 average rating, 135 reviews

Charming Country Cottage

Aug 28 – Sep 4

R11,277 ZAR per night

Family- and pet-friendly home rentals

Home in Dorset

4.86 out of 5 average rating, 117 reviews

Modern Olympic eco-house Dorset by the sea

Oct 6 – 13

R4,403 ZAR per night

Home in Easton

4.94 out of 5 average rating, 131 reviews

Top To Bottom beautiful cottage heart of Easton

Nov 22 – 29

R3,293 ZAR per night

Guest suite in Cattistock Dorchester

4.9 out of 5 average rating, 369 reviews

Willow Annexe

Aug 16 – 23

R1,852 ZAR per night

Bus in Owermoigne

4.85 out of 5 average rating, 224 reviews

Magic Bus RV nr coastal Durdle door play garden

Oct 16 – 23

R1,704 ZAR per night

Cottage in Hooke

4.93 out of 5 average rating, 225 reviews

The Little House, Hooke, Nr Bridport, West Dorset

Oct 7 – 14

R2,964 ZAR per night

Guest suite in Duntish

4.91 out of 5 average rating, 403 reviews

Duntish Studio

Sep 12 – 19

R1,426 ZAR per night

Bungalow in Dorset

4.95 out of 5 average rating, 151 reviews

Dairy House Self Catering Annexe

Nov 29 – Dec 6

R3,223 ZAR per night

Home in Shaftesbury

4.99 out of 5 average rating, 441 reviews

Private, with incredible views

Feb 17 – 24

R2,968 ZAR per night

Family-friendly home rentals with a pool

Chalet in Weymouth

4.93 out of 5 average rating, 120 reviews

Bowleaze Cove with a view

Aug 31 – Sep 7

R3,012 ZAR per night

Apartment in Whitchurch Canonicorum

4.94 out of 5 average rating, 235 reviews

The Duck Wing, quirky dog friendly apartment

Apr 13 – 20

R2,447 ZAR per night

Guesthouse in Swanage

4.86 out of 5 average rating, 142 reviews

Swanage Sands Vegetarian/Vegan Studio

Sep 11 – 18

R2,537 ZAR per night

Home in Preston Road

4.83 out of 5 average rating, 108 reviews

Haven Weymouth Bay Holiday Park

Aug 2 – 9

R3,788 ZAR per night

Home in Long Sutton

4.79 out of 5 average rating, 460 reviews

Somerset Cider Barn Bliss: Tub, Pool, Pubs, Walks

Oct 14 – 21

R3,093 ZAR per night

Chalet in Dorset

4.94 out of 5 average rating, 230 reviews

Breathtaking sea views from this light, cosy lodge

Feb 8 – 15

R3,360 ZAR per night

Cabin in Forton

4.89 out of 5 average rating, 149 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

Jan 24 – 31

R2,457 ZAR per night

Cottage in Sherborne

4.91 out of 5 average rating, 394 reviews

Secret Rural Retreat

Oct 5 – 12

R3,223 ZAR per night

Destinations to explore