Holiday rentals in Southend Chalkwell Beach

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Top-rated holiday rentals in Southend Chalkwell Beach

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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
5 out of 5 average rating, 116 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
Flat in Southend-on-Sea
4.98 out of 5 average rating, 316 reviews

The Lookout - Thorpe Bay beach apartments

The Lookout is situated directly on the sea front between Southend on sea and Thorpe bay. We have stunning sea views and our balcony is the perfect place to watch the sunset over Southend pier. The beach is right outside our front door and a 15 min walk along it will take you to Southend sea front, with its many arcades and Adventure island. The 1 bedroom luxury apartment has a king size bed, south facing balcony, full kitchen, stylish wet room, 50" curved tv, free wifi and a log burner.

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, 367 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!

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.
Apartment in Thorpe Bay
4.99 out of 5 average rating, 415 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
A sandy beach stretches along the shoreline, meeting calm waters under a clear blue sky. A boat is anchored nearby, adding a nautical touch to the tranquil scene. Distant figures can be seen enjoying the beach, emphasizing the area's inviting atmosphere.
Flat in Leigh-on-Sea
4.82 out of 5 average rating, 78 reviews

Seaside and private garden apartment.

One bedroom ground floor flat with very peaceful garden. The property is lovely and cosy and has direct access to your very own garden. If you walk left when you exit the front door you will find yourself right at the beach. If you turn right you will come across an array of independent restaurants, bars and little bespoke shops selling their beautiful items. Please be aware this bathroom is been refurbished and from February will have a walk in shower not a bath.

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, 110 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.

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
4.91 out of 5 average rating, 91 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 self-contained lodge is shown with a decorative privacy panel beside a wooden bench. Flowering plants are placed nearby, and a grassy area extends alongside the path leading to the entrance. A window and door are visible on the lodge's exterior, confirming its inviting design.
Guest suite in Southend-on-Sea
4.88 out of 5 average rating, 208 reviews

Quiet and cosy self-contained garden lodge.

The Hutch is in Leigh-on-Sea, close to parks, Southend Airport (3.9miles), shops (0.5miles for Leigh-on-Sea & 3.9miles for Southend High Street), the Estuary (1.5miles), Cliffs Pavilion (2.3miles) and the hospital (1.5miles). You’ll love my place because of the location, it's privacy as it's a self-contained lodge with its own access, and courtyard as well as off street parking My place is good for couples, solo adventurers, and business travelers.

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.
Flat in Leigh-on-Sea, Southend
4.97 out of 5 average rating, 181 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.

Superhost
A spacious living area is highlighted by a light-toned sectional sofa, a decorative rug, and a dining space for two. Soft lighting is provided by a stylish chandelier, while large windows offer views of the outdoors. A modern kitchen is visible in the background.
Serviced apartment in Southend-on-Sea
4.76 out of 5 average rating, 51 reviews

Two Bedroom Apartment Sea View Westcliff CA12

TWL Properties are delighted to bring to the market this outstanding luxury development, offering 13 stunning 1 & 2 bedroom serviced apartments. Located opposite the Cliffs Pavilion and just moments from Westcliff Beach and Chalkwell Park. Westcliff train station for the C2C train, which provides easy access to London via London Fenchurch Street, is only 0.3 miles away. Southend Airport is under 10 minutes drive.

Guest favourite
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
4.94 out of 5 average rating, 79 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

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, 50 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.

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