Family-friendly vacation rentals in Skegness

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Top-rated family-friendly rentals in Skegness

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

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Top guest favorite
The exterior of a charming brick annex is visible, featuring distinctive arched windows framed by greenery. The facade is adorned with hanging flower baskets, adding a touch of colour. A gravel driveway offers ample parking space, contributing to a welcoming entrance.
Home in Lincolnshire
4.92 out of 5 average rating, 221 reviews

The Annex @ Ormiston House

*AUGUST SPECIAL OFFERS* The Annex@Ormiston offers unique accommodation for up to 4 guests, in a self-contained building adjacent to our family home. It has ample private parking, a secure entrance, a private courtyard and access to a large garden. Downstairs, there's a kingsize bedroom, shower room, lounge and fully equipped kitchen. Upstairs, an additional bedroom contains one or two single beds. The property is a 10 minute walk from the town centre and less than a mile from Pilgrim Hospital.

Guest favorite
The charming cottage exterior features rustic brick walls and a pitched roof, framed by lush green foliage and flower beds. Seating areas with wooden chairs are situated on the lawn, inviting relaxation amidst the serene garden surroundings.
Cottage in Hagworthingham
4.94 out of 5 average rating, 240 reviews

Fairytale Cottage in a Beautiful Garden

Step into this dreamy cottage, secluded within its rambling sunny gardens with ample seating to enjoy the view. Delight and relax in its thoughtfully curated interior. Wake up refreshed within pretty bedrooms tucked into the eaves, and look out over the garden with constant soundtrack of birdsong. Relax by the log burner, or fire up the BBQ after you explore the walks which extends beyond the country lane, even if you only venture as far as the delicious cosy gastro pub, cafes & farm shop nearby

Guest favorite
An outdoor deck area features comfortable seating with dark wicker furniture, providing views of sandy dunes and the sea. A glass balustrade surrounds the space, allowing unobstructed sightlines of the coastal landscape. Natural light fills the area, enhancing the inviting atmosphere.
Cottage in Anderby Creek
4.92 out of 5 average rating, 289 reviews

Beach-front cottage. Sea view from every room.

Anderby Creek was voted one of the UK's best undiscovered beaches by AOL, The Times & The Telegraph. The house has simply beautiful views of the beach, sea and sand dunes with extensive decking surrounded by glass balustrade where you can sit outside and enjoy the sea air. It's a family home, fully centrally heated and comfortable. Expect mismatched crockery & imperfection! It's a steep drive up to the house & steps to the beach (although you can go around the drive way) so not suitable for all

Top guest favorite
A quaint yellow cabin is nestled among lush greenery. A wide wooden deck features a glass-topped table surrounded by wicker chairs, creating an inviting outdoor dining space. The warm colors of the cabin contrast with the vibrant leaves overhead.
Hut in Stewton
4.98 out of 5 average rating, 128 reviews

Stunning family glamping retreat- tranquil setting

Welcome to Stewton Stars Hideaway ✨ A multi-award winning retreat located near Louth (East Lincolnshire). An idyllic, peaceful location set nestled between the pretty green hills of the Lincolnshire Wolds (AONB) and golden sands of the Lincolnshire Coast. *IMPORTANT NOTE* This cabin is for families to enjoy (children must be 2 or over). Only peaceful family adult group bookings will be accepted. We are not a place to party and anyone not respecting this will be asked to leave without refund.

Top guest favorite
The tranquil river reflects the surrounding greenery and the rustic barn structure. A pontoon is visible by the water's edge, alongside outdoor seating that invites relaxation. Trees frame the scene, creating a peaceful atmosphere for enjoying nature.
Barn in Brothertoft
4.98 out of 5 average rating, 210 reviews

The Barn at White House Farm 1800's 3 bed Barn

The Barn is situated in the grounds of White House Farm, on the banks of the River Witham. It's a wonderfully cosy and private barn conversion with a separate private garden which is fully enclosed ideal for Dogs. Self-contained, 2 bedrooms, newly renovated bathroom, kitchen, wood burner and 65” HD TV with Netflix and Free WiFi. Quiet and very peaceful. We also now have a pontoon on The River behind the Barn from which you can launch your paddle boards, canoes or even go wild water swimming!

Guest favorite
A two-story Edwardian-style house is framed by a well-maintained garden. The exterior features a mix of large windows and attractive gables, with a welcoming entrance. Lush greenery provides a natural border, enhancing the property's inviting presence.
Villa in Skegness
4.83 out of 5 average rating, 103 reviews

Lilac Villa Skegness

Lilac Villa is a very large and beautiful 5 bedroom Edwardian Style House, dated 1906, converted to a Holiday Home in Skegness. Just five minutes walk to the beach (dog friendly )and to the Sea Front and main promenade. The property is located in the quieter North part of the town, however it's only a 10 minute walk to the town centre. From the kitchen are double french doors onto the deck. Which has seating and a barbecue for your use. The garden is enclosed with a firepit and grass area.

Top guest favorite
The lodge's exterior showcases a modern wooden design with a sloped roof. Large glass doors reflect the warm glow of the sunset, while a stone pathway leads to a seated area with wooden chairs and tables on the manicured lawn, surrounded by greenery.
Cabin in Hogsthorpe
4.99 out of 5 average rating, 232 reviews

Wren Lodge W/ Alpacas, Goats & Sheep | Wren Farm

Located at Wren Farm, our brand new to 2023 luxury lodge situated besides the alpaca fields, with Wren Farm Desserts cafe on site. Also near beaches, Skegness, Chapel, Mablethorpe, etc. We are dog friendly! Fully stocked (cutlery) Has 1 double bed and a sofa bed that sleeps 2. Private bathroom with shower. Surrounded by green fields, beautiful animals and excellent food! Add ons available on request - Ploughman's Grazing Box, Breakfast Boxes. Alpaca trekking also available.

Guest favorite
A spacious indoor heated pool area features a serene swimming pool surrounded by artificial grass. Expansive windows allow natural light to flood the room, framing views of the outdoor landscape. Comfortable seating areas are placed nearby, creating a relaxed atmosphere.
Barn in Kirkby on Bain
4.95 out of 5 average rating, 264 reviews

Luxury Annex beside the River Bain Nr Woodhall Spa

A most beautiful luxury annex to the main residence , with an indoor heated luxury swimming pool and 2 person sauna infrared.The property is set on the River Bain ,with open views to the Bain valley. . The pretty village of Kirkby on Bain is just 600 yards away. The Ebbington Arms is a wonderful public house which is well renowned for its excellent food. The Edwardian inland resort of Woodhall Spa is just 4 miles away here you find fantastic restaurants, shops and wonderful walks.

Top guest favorite
Cottage in Spilsby
4.96 out of 5 average rating, 143 reviews

Retreat to a former Chapel, relax in privacy.

With unspoilt views over countryside, our former Chapel on the Lincolnshire Wolds doorstep offers the perfect place to enjoy a memorable relaxing stay. Visit all that this County has to offer, including miles of lovely beaches, followed by snug winter evenings in front of a Log Burner, or warm summer evenings relaxing on the Patio, perhaps observing the wildlife. There is a myriad of tracks and paths around for walkers and cyclists alike. We offer comfort with a homely feel.

Top guest favorite
The exterior of a uniquely shaped wooden pod is depicted, featuring a sloping roof and a large arched window. The door is made of natural wood and is flanked by potted plants. The pod is surrounded by greenery, including shrubs and flowering plants.
Place to stay in Lincolnshire
4.95 out of 5 average rating, 166 reviews

♥cosy; parking; garden; rural cycle/walks+more

Idyllic, rustic, quiet self contained private 1 bed Pod in the meadow style garden of a Victorian house on the edge of the Lincolnshire Wolds and also within walking distance of Horncastle market place, shops and amenities. Private entrance with self check in and own parking space, use of large garden, galley kitchen (with sink, small fridge, microwave), dining area and bedroom (double bed) with en-suite suitable for 1-2 adults only (sorry no children or pets).

Guest favorite
A wooden fence encloses a garden with a mature apple tree bearing numerous green apples. The cottage is visible through an open window, framed by lush greenery. Bright sunlight highlights the inviting facade of the cottage and the surrounding foliage.
Condo in Snettisham
4.83 out of 5 average rating, 387 reviews

A Getaway on Norfolk's wonderful coast

Enjoy separate, self-contained accommodation at Apple Tree Cottage! A comfortable bedroom with a double bed, bathroom, kitchen and private garden. Enjoy rambling Wild Ken Hill, woods and fields as featured in BBC's Nature Watch , a short walk away. RSPB Snettisham a world renowned bird haven . Spectacular sunsets on the beach. The Old Bank and The Rose and Crown are in the heart of the village for dining. Wonderful coastal excursions .

Top guest favorite
A private terrace featuring a hot tub is shown, with two chairs positioned nearby. The surrounding fence provides added seclusion, and light blue doors lead into the cottage. Clear blue skies and sunshine enhance the inviting outdoor space.
Cottage in Market Rasen
4.97 out of 5 average rating, 746 reviews

Bluebell Cottage, Wolds Retreat, Hot Tub. Walesby

A peaceful retreat. One of two semi detached converted stables. Open plan lounge/kitchen/diner, king bedroom, en-suite freestanding bath. Beautiful views. Surrounded by deer, sheep & horse paddocks. Terrace, seating and hot tub for private use of Bluebell cottage (not shared) No music outside please. Enjoy nature’s soundtrack ❤️ Parking. Wifi. Lincolnshire Wolds. Viking Way & Lindsey Trail for walking/cycling.

Popular amenities for Skegness family-friendly rentals

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Avg. priceG$24,200 GYDG$25,869 GYDG$20,237 GYDG$22,531 GYDG$23,157 GYDG$22,949 GYDG$26,495 GYDG$31,502 GYDG$23,783 GYDG$20,445 GYDG$20,237 GYDG$21,071 GYD
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Quick stats about vacation rentals that are family-friendly in Skegness

  • Total vacation rentals

    Explore 350 vacation rentals in Skegness

  • Nightly prices starting at

    Skegness vacation rentals start at G$10,431 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,650 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 180 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    250 of Skegness vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Skegness rentals

  • 4.6 Average rating

    Skegness stays receive an average rating of 4.6 out of 5 from guests