Holiday houses in Southend Chalkwell Beach

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Top-rated holiday rentals in Southend Chalkwell Beach

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A dining area features a round table set for four, accompanied by stylish chairs. Natural light fills the space through a nearby window. A decorative mirror and woven pendant light add inviting elements to the warm, neutral tones of the room.
Cottage in Southend-on-Sea
4.84 out of 5 average rating, 51 reviews

Luxury Heritage Cottage in the Heart of Old Leigh

A beautifully refurbished 2 Bedroom Heritage Fisherman's Cottage with historic charm & modern comfort. This cosy cottage in the heart of Old Leigh offers stunning sea views & a warm, stylish retreat. Perfect for couples or small families. 🧺 Welcome basket 🌊 Sea views 🧳 Long stays welcome 🏖️Waterside Balcony ❤️ Ideal for romantic getaways & family breaks 💻Excellent Wifi 🛁 2 Bathrooms Steps from Leigh-on-Sea’s coastal walks, boutique shops & renowned seafood spots-all within easy reach.

LocationFamilyGetting around

Top Guest favourite
A serene view of the sea features multiple sailboats gently bobbing on the calm water. The scene is set against a clear blue sky, creating a peaceful atmosphere that invites relaxation and enjoyment of the coastal surroundings.
Home in Leigh on Sea
4.87 out of 5 average rating, 101 reviews

Stunning sea views. Local for beach & eateries

Situated in Leigh on Sea, a stunning 2 bedroom maisonette a stones throw from the beach. You have clear sea views from both bedrooms, kitchen and sitting room There is a private balcony leading from both bedrooms and also from the sitting/dinning room. All balconies have seating to allow you to relax and read a book or have your morning cuppa. Whichever way you walk you will find tasty restaurants and cute coffee bars within minutes. Available on the beach-sup lessons, photography & yoga.

LocationFamilyQuiet

Top Guest favourite
A spacious studio area features a double bed with a floral-patterned duvet and two large cushions. A mirror and a hanging rack with clothes hangers are positioned beside a shelf with decorative items, complemented by soft natural light from the window.
Guest suite in Southend-on-Sea
4.94 out of 5 average rating, 68 reviews

Bright and Cozy 1-bed studio near Southend Airport

Relax in this comfortable studio, perfectly located just minutes from Southend Airport. Featuring a double bed, inviting lounge area, and a private en-suite bathroom, it’s ideal for a restful night before or after your travels, or for if you’re visiting family/weddings. Enjoy complimentary tea and coffee making facilities to start your day right. Tucked away in a peaceful location, yet close to transport links, shops, and local attractions, this studio offers convenience and comfort in one.

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Top Guest favourite
A serene outdoor space is presented, featuring two loungers on a green lawn beside a tranquil pond. Lush vegetation surrounds the water, and a stone barbecue is visible in the background, framed by a clear blue sky with scattered clouds.
Guesthouse in Essex
4.99 out of 5 average rating, 192 reviews

Meadow water view peaceful countryside with ducks

Private Cosy getaway in the English countryside Whether you want to take advantage of the many local coastal & woodland walks or stroll to the local country pub Or just have some time to yourself & cosy up in the lodge or relax in the garden & feed our ducks You will have the entire lodge to yourself so you will not be disturbed it has its own private entrance as outlined in green on the photos Contactless check in No smoking in the lodge No parties Maldon high street is a 10 min drive

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Top Guest favourite
A spacious living area features plush green sofas arranged around a central coffee table. A large decorative mirror reflects light, while a modern chandelier hangs above. Natural light pours in through large windows, dressed with elegant shades.
Home in Southend-on-Sea
4.99 out of 5 average rating, 134 reviews

Amazing house with sea views in Leigh-on-Sea

Amazing character 3 storey house dating from 1860’s with sea views, modernised and expanded in 2009 to provide 3 king size luxury bedrooms, (2 with en-suite) 1 large dressing room, 1 large family bathroom with bath, sink, large walk on shower and double sinks and large open plan ground floor set over two levels with large luxury sitting room, stepping down to open plan dining area, kitchen with central island unit and rear seating area with bi-fold doors opening onto a luxury garden area.

LocationFamilyGetting around

Guest favourite
An elegantly designed bedroom features a spacious super king bed adorned with soft linens and stacked towels. A freestanding bath is positioned nearby, complemented by wooden wall accents. A cozy robe hangs in the background, while soft lighting contributes to a serene atmosphere.
Farm stay in Essex
4.98 out of 5 average rating, 391 reviews

Exclusive retreat on a private lake

Enjoy a truly unique stay in this exclusive lodge. Situated on its own private lake, you will have everything you need to enjoy a blissful retreat with award winning country pubs such as The Dog & Pickle only a walk away. Please note: 1. We are strictly a minimum of two night stays. 2. We can only accept infants under 6 months old. 3. There is no swimming or paddle boarding allowed in the lake. NEW FOR 2026 - The Wellness Deck Sauna, Cold Plunge & outdoor shower, ready for use now!

FamilyValueHot tub

Top Guest favourite
A balcony view is captured through bi-fold glass doors, featuring a small round table and two folding chairs. A decorative pumpkin sits at the center, with panoramic sea views of the estuary and boats in the distance, framed by a serene sunset.
Condo in Thorpe Bay
4.99 out of 5 average rating, 436 reviews

Estuary Views Penthouse with Private Parking

A Beachfront Coastal Retreat with private driveway parking & situated in the sort after area Thorpe Bay. Boasting unspoilt Panoramic Sea Views. Central to Blue Flag Beaches, 2 mins from award winning restaurants, superb location for coastal walks, watching the seabirds & a short walk to the longest Pier in the world. Re-Designed with Bi-Folding Glass doors, bringing the Outside Inside. Intricately Designed embracing tiny details that define our property for a Luxury & cosy stay.

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Superhost
An open living area features a modern gray sofa, sleek cabinetry, and a wall-mounted television. Large windows offer views of the surrounding landscape. The wooden flooring, designed in a herringbone pattern, complements the light wood paneling and cabinetry throughout the space.
Barn in Kent
4.86 out of 5 average rating, 123 reviews

Oak Lodge @ The Oaks Retreat

This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Oak Lodge offers 2 king size bedrooms fully customized with high-end finishes which to need to be seen in person to be fully appreciated. Our Wellness area is equipped with a log burning sauna, a cold plunge and outdoor shower.

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Guest favourite
A cozy bedroom features a spacious bed with neutral bedding and decorative pillows. Two bedside lamps provide soft lighting, and framed artwork is displayed above the bed. Light-colored walls and wooden flooring contribute to a fresh and clean ambiance.
Apartment in Southend-on-Sea
4.88 out of 5 average rating, 99 reviews

Cozy brand new serviced apartment

A beautifully designed one bedroom apartment, recently refurbished to a high standard. Dream Yard is situated in the heart of the vibrant Hamlet Court Road with immediate access to cafes, restaurants and shops. Less than five minutes to the Westcliff train station and less than 10 min to the beach. The flat is self catered comprising bedroom, shower, kitchen and living room with access to the Chéri’s Cafe. Guests enjoy 10% discount on food.

FamilyValueLong stay

Top Guest favourite
A cozy bedroom is presented with a double bed featuring an ornate headboard. Two cushions in navy blue rest on the crisp white linens. A piece of wall art depicting vibrant lips adds a pop of color. A flat-screen TV is mounted on the wall opposite the bed.
Apartment in Leigh-on-Sea, Southend
4.97 out of 5 average rating, 203 reviews

Lovely studio for two in central Leigh on Sea

This is a very calm space decorated in F&B elephants breath paint with contrasting furnishings. A double bed + a sofa bed + travel cot. Cooking facilities, dining table table & 2 chairs. A microwave is situated in the utility room on the landing outside the studio door. Very nice shower room It’s ideal as a compact living space to use when visiting relatives or just on a break in lovely Leigh on Sea. No outside space is available.

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Superhost
A spacious living area is highlighted by soft green walls and extensive windows, allowing natural light to fill the room. Two plush green sofas and a wooden coffee table complement the décor. A dining area in the background offers views of the marina through large windows.
Houseboat in Southend-on-Sea
4.9 out of 5 average rating, 99 reviews

The Pontoon | Beautiful Leigh Marina

Escape to The Pontoon - Your Floating Retreat at Leigh Marina Welcome to The Pontoon, an exquisite houseboat moored at the picturesque Leigh Marina. This stunning floating property offers an unparalleled blend of comfort and adventure, perfect for families, friends, or couples seeking a unique getaway. This stunning home offers fast Wi-Fi and free parking. Professionally managed by Pass The Keys

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Top Guest favourite
An open-plan kitchen and dining area is visible through bifold doors, creating a seamless connection to the outdoor courtyard. Tall bar stools align a light wood dining table, with soft seating arranged around a low table adorned with snacks and glasses. Potted greenery enhances the inviting space.
Home in Southend-on-Sea
4.96 out of 5 average rating, 56 reviews

Stunning house in the heart of Leigh-On-Sea

Beautifully restored 3 bedroom detached house in the very heart of the vibrant and trendy Leigh on Sea Broadway moments from the bars, boutiques, galleries and coffee shops and just a short walk to the sea. A collaboration between Mother and Daughter, Interior Designer, Nathalie Brandajs and Artist, Caron Brandajs, who transformed and beautifully styled this period property.

LocationFamilyParking

Popular amenities for Southend Chalkwell Beach holiday rentals