Holiday houses in Southend Chalkwell Beach

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Southend Chalkwell Beach

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

1 of 1 pages1 / 1
Guest favourite
Condo in Southend-on-Sea
4.95 out of 5 average rating, 19 reviews

Apartment heart of Leigh on Sea. 2 double bedrooms

A stunning 2 double bed flat in the centre of Leigh. Up to 4 guests. In heart of the shops, cafes, music bars & amazing restaurants. Everything else is a couple of minutes walk! From the beach, bus stop outside train station & The Broadway. 9 mins to the airport. 2 modern double bedrooms, sleek, clean & modern bathroom & kitchen as well as spacious living area to enjoy. Situated above a designer shop overlooking the fabulous bars, eateries & shops of Leigh. No stags/hens no pets no smoking

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 Southend-on-Sea
4.87 out of 5 average rating, 103 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.

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, 136 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.

Top Guest favourite
A two-story white building features large glass panels on the front, allowing natural light to illuminate the interior. The entrance is accentuated by decorative stone columns on either side. A paved area with gravel is visible in the foreground.
Guest suite in North Benfleet
4.97 out of 5 average rating, 464 reviews

Adorable 4 bedroom annex with hot tub

Welcome to 'The Annex' a super hidden gem, tucked away in a rural location but only 11 miles to Southend seaside with 'Adventure Island', 8 miles to Leigh-on-sea and only 33 miles from London. Nestled between the A13 and A127. 'The Annex' is the perfect setting for special occasions, birthdays, families, contractors, hens, stags, holidays, treat yourself time. Take time to relax in the bubbly hot tub. It's important to look at 'other details to note' for rules on events and celebrations.

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 Southend-on-Sea
4.99 out of 5 average rating, 439 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.

Guest favourite
Apartment in Southend-on-Sea
4.86 out of 5 average rating, 160 reviews

Spacious homely seaside maisonette with balcony

This charming two-floor flat offers comfort and convenience. You’re ideally located minutes from the Cliffs Pavilion, cliff gardens, and seafront. The station is a 4-minute walk for quick links to London. Leigh on sea with its vibrant cafes and boutique shops is 2 stops away and the airport is a 10-minute drive. Enjoy the games room including table football, darts, and a PS4. With nearby restaurants, shops, and Adventure Island, there is something for everyone.

Top Guest favourite
A patio area features a round table set for two, accompanied by metal chairs. A tray holds glasses and a bottle, with a view of the estuary visible in the background. The surrounding greenery complements the outdoor ambience.
Cottage in Southend-on-Sea
4.92 out of 5 average rating, 99 reviews

Bright modernised cottage with Estuary views

A fisherman's cottage set in a tucked away corner of Old Leigh with its many pubs and restaurants, just a short walk up the hill to the Broadway with its bustle of shops and coffee bars. Double bedroom, shower room, fully equipped kitchen with oven, hob, Smeg fridge, dishwasher and washing machine. Comfortable lounge, couch and 42" smart TV. A large patio with table and benches, steps leading to lawn. Estuary view from shower room, kitchen and sitting room.

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, 100 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.

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 Southend-on-Sea
4.97 out of 5 average rating, 208 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.

Top Guest favourite
Apartment in Southend-on-Sea
5.0 out of 5 average rating, 16 reviews

Spacious 3BR Flat - Heart of Leigh Dining Scene

Stylish 3-bedroom flat in the heart of Leigh-on-Sea, set on its vibrant restaurant street. Enjoy top dining, bars, and cafés right on your doorstep, with the seafront just a short stroll away. Perfect for families, groups, or business stays, offering comfort, space, and unbeatable access to everything this lively coastal town has to offer. Free parking available in the neighbourhood for added convenience.

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, 103 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

Superhost
Home in Southend-on-Sea
4.68 out of 5 average rating, 22 reviews

10% Off |7 Nights |Family lSleep 9 |Parking |WiFi

A spacious 5-bedroom home just minutes from Westcliff Beach, perfect for families or groups. Enjoy a fully equipped kitchen, large garden, games room, and cosy lounge. With shops, transport links, and the seafront on your doorstep, it’s the ideal base for exploring Southend-on-Sea. Sleeps up to 9 guests with free parking, fresh linens, and everything you need for a comfortable stay.

Popular amenities for Southend Chalkwell Beach holiday rentals