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Family-friendly vacation rentals in Isle of Portland

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Top-rated family-friendly rentals in Isle of Portland

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Cottage in Dorset

4.87 out of 5 average rating, 326 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...

Cottage in Portland

4.82 out of 5 average rating, 133 reviews

Cosy cottage with Sea Views. Central location

Sea View Cottage is a historic 200+ year old stone merchant's house just minutes from the beach, offering stunning sea views from the living room, bedrooms, and sun deck. The property sleeps 5, featuring a cozy lounge with woodstove, dining area with workspace, well-equipped kitchen, and bathroom with large electric shower. Bedrooms include a first-floor double bedroom and a second-floor bedroom with three singles. Perfect for a relaxing seaside getaway with modern comforts and historic charm.

Townhouse in Dorset

4.87 out of 5 average rating, 135 reviews

Historic Seaman Chaplaincy, Seaview all rooms

The Gift House Portland is a historic Seaman's Chaplaincy, 3 storey late georgian stone house. All 4 spacious bedrooms have pano sea view & perfect for sunset watching. Dog friendly. Locate in island village, 5 mins walk to pebble beach(part of Jurassic coast), 17th century pub, restaurant, good coffee cafe, chippy & Co-op shop. Portland island is a hidden gem, Jurassic coast walks, cycling, swimming , rock climbing, sea fishing, diving, kayak, sailing, paddling, windsurf & more around

Guesthouse in Dorchester

4.97 out of 5 average rating, 300 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.

Cottage in Dorset

4.97 out of 5 average rating, 190 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!

Barn in Symondsbury

4.82 out of 5 average rating, 268 reviews

"The Nest" Cosy ground floor mini-barn conversion

The Nest is our charming GROUND FLOOR STUDIO apartment in a converted barn from the 1800’s. Set in “Broadchurch country” in the village of Symondsbury, it is a short drive to Bridport, West Bay & several beautiful beaches along Dorset's Jurassic coast. With a 16th Century pub 500 yards away with great food it sits at the foot of the famous Colmers Hill. The area is well known for walking. Perfect for guests of weddings at The Tithe Barn, Idyllic place for couples

Townhouse in Dorset

4.93 out of 5 average rating, 105 reviews

Sailor's Watch: A beautiful home by the sea...

A spacious Grade 2 Listed Dutch Style harbourside merchant house which has been split into two homes. You will be renting our home which spans across the first and second floors. It has been recently refurbished and has wonderful views of the harbour. There is a garden out the back with table and chairs. Close to the main town, beach and amenities of Weymouth. Dogs will be charged at £20 each per booking, please let me know if you are bringing your dog with you.

Cottage in Dorset

4.99 out of 5 average rating, 339 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!

Place to stay in Weymouth

4.95 out of 5 average rating, 239 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.

Condo in Dorset

4.95 out of 5 average rating, 304 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

Rental unit in Weymouth

5 out of 5 average rating, 425 reviews

Apartment with panoramic sea views

We are situated 600 yards, through the nature reserve, from the beach and at the top of the hill with panoramic views over Weymouth bay, beach and nature reserve. 3 miles from the town With loads of parking available outside .You’ll love my place because of the location, the views. good for couples, solo adventurers, business travellers and small, well behaved dogs.

Cottage in Dorset

4.85 out of 5 average rating, 379 reviews

Character cottage close to beach

Spacious and beautiful house 5 min walk to Chesil Beach. Free superfast wi-fi, well equipped kitchen including dishwasher and a cosy log burner in living room. Scandi style décor. Netflix and smart TV. Right in heart of Fortuneswell, Portland with some shops, pubs and restaurants close by. 10-15 min drive from Weymouth. Great for couples.

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Popular amenities for Isle of Portland family-friendly rentals

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Family-friendly home rentals with a hot tub

Home in Bridport

4.91 out of 5 average rating, 46 reviews

Moorbath Farmhouse with Indoor Pool & Hot Tub

Cottage in Woolland Dorset

4.86 out of 5 average rating, 14 reviews

Dogs welcome! Hot tub hideaway for 4 rural Dorset

Home in Toller Porcorum

4.94 out of 5 average rating, 66 reviews

Frogmore House near Jurassic Coast with hot tub

Cottage in Dinnington

4.95 out of 5 average rating, 477 reviews

The Cottage, Parsonage Farmhouse with hot tub

Hut in Dorset

4.94 out of 5 average rating, 84 reviews

Astronomer Shepherd's hut

Cottage in Dorchester

4.98 out of 5 average rating, 185 reviews

Charming Brick Cottage with a Patio and Hot Tub

Home in Alton Pancras

4.97 out of 5 average rating, 79 reviews

Little Coombe, a luxury rural cottage with Hot tub

Townhouse in Dorset

4.85 out of 5 average rating, 106 reviews

Spa Cottage in Weymouth, Dorset

Family- and pet-friendly home rentals

Religious building in East Stoke

4.9 out of 5 average rating, 114 reviews

Amazing converted church -Dorset’s Jurassic Coast

Home in Portland

4.94 out of 5 average rating, 33 reviews

Stonehall; the Vestry, Stonehouse and Great Hall

Guest suite in Morcombelake

4.91 out of 5 average rating, 423 reviews

Modern studio, hillside garden with amazing views

Rental unit in Bridport

4.86 out of 5 average rating, 436 reviews

The Old Bakery

Home in Bishop's Caundle

4.76 out of 5 average rating, 490 reviews

Ryalls Stud Cottage

Cottage in Chideock

4.86 out of 5 average rating, 206 reviews

Idyllic views, quiet,cosy, Jurassic coast cottage

Tiny home in Dorset

4.9 out of 5 average rating, 230 reviews

North End Farm, Old Cricket Pavilion

Home in Beaminster

4.91 out of 5 average rating, 125 reviews

Wantsley Cottage

Family-friendly home rentals with a pool

Chalet in Dorset

4.97 out of 5 average rating, 38 reviews

Chesil Holiday Lodge, Weymouth *sea views*

Cottage in East Coker

4.94 out of 5 average rating, 34 reviews

The Cottage at Flo’s Cottages with Indoor Pool

Home in Whitchurch Canonicorum

4.83 out of 5 average rating, 53 reviews

Large peaceful home very near the sea with pool.

Home in Preston Road

4.84 out of 5 average rating, 111 reviews

Spacious Caravan near sea Weymouth Bay Haven

Home in Near Sherborne

4.86 out of 5 average rating, 21 reviews

17th c. Rural Mill House with Pool

Cabin in Mills Road, Osmington Mills, Weymouth, Dorset

5 out of 5 average rating, 41 reviews

Luxury Cedar Lodge: Dorset Jurassic Coast

Home in Weymouth

5 out of 5 average rating, 19 reviews

Driftwood (BV09), Silverlake, Dorset

Home in Blandford Forum

4.98 out of 5 average rating, 50 reviews

Flint Cottage for two with indoor pool & sauna

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