Holiday rentals in Southend Chalkwell Beach

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Top-rated holiday rentals in Southend Chalkwell Beach

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Top guest favourite
Guest house in Kent
4.92 out of 5 average rating, 118 reviews

'The Hideaway ' Sole Street, Cobham, Kent.

The Hideaway is situated in the heart of Kent in the rural village of Sole Street, Parish of Cobham & Luddesdown. We are walking distance to Sole Street Station on the Victoria line to London. Ebbsfleet & Meopham are a driving distance away so St Pancras and Victoria can be reached in 17 - 35 minutes. The location is great for people who love long walks & nature as we are surrounded by ancient unspoilt woodlands and rolling hills. We have a choice of three Forestry Commission Parks to visit.

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, 112 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, 306 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
A comfortable living area features a gray sectional sofa accented with yellow cushions, paired with a blue dining set. A glass dining table is centered in the space, and a wall-mounted television overlooks a modern wooden shelf. Natural light filters through large windows adorned with white blinds.
Flat in Southend-on-Sea
4.9 out of 5 average rating, 114 reviews

The Alvaros Apartment

The Alvaros apartment is completely refurbished to a high standard and is based just a ten minute walk to Westcliff seafront where you can stroll along to towards Southend Pier and other attractions. The apartment is close to Westcliff Train Station and Hamlet Court Road where you will find shops, bars and restaurants. The apartment is connected to Alvaros Fine Dining Portuguese Restaurant where guests staying can enjoy a 10% discount on meals and drinks (open Tuesday to Sunday evenings).

Top guest favourite
A modern living area features a deep blue accent wall with a mounted television and a stylish electric fireplace. A small dining table with chairs is set alongside a vibrant piece of wall art. Sunflowers are arranged in a vase, adding a touch of color.
Apartment in Southend-on-Sea
4.97 out of 5 average rating, 62 reviews

Sunflower - Westcliff Apartments

Stunning, newly refurbished to a high standard, this ground floor Westcliff Apartments flat is situated a stones throw from the Cliffs Pavillion, estuary gardens and views, the esplanade, the renowned 'arches' cafes, train station, restaurants and a park. Within walking distance of Southend amenities, pier, beach and shops, and a short drive to old Leigh. Quiet location but close enough to everything the area has to offer. Especially great for the theatre or walks along the sea front.

Top 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, 359 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, 407 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.

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, 101 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 spacious bedroom features a king size bed with neutral bedding, flanked by bedside tables and lamps. French doors open to a private patio, bringing in natural light and garden views. The herringbone-patterned floor adds warmth to the inviting space.
Flat in Southend-on-Sea
4.99 out of 5 average rating, 167 reviews

Spacious g/f one bedroom annexe - Leigh on Sea

This spacious ground floor one bedroom annexe is situated in the charming town of Leigh-on-Sea. The annexe is joined to the main building by a locked acoustic door. A two minute walk to Bonchurch Park and a short walk to Belfairs Nature Reserve. Plenty of local shops within a 5-15 minute walk and a 20-30 minute walk to Leigh broadway, Old Leigh/beach and Leigh station. EV charger available. A small south-facing patio available for guest use. Off-road parking space.

Guest favourite
The lounge/diner features a cozy sofa and a leather seating area, complemented by a dining table set for six. Natural light fills the space through large windows, and decorative pieces are displayed on the walls. A warm ambiance is created by the overhead chandelier.
Flat in Southend-on-Sea
4.87 out of 5 average rating, 119 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.

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
4.89 out of 5 average rating, 193 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, 176 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.

Popular amenities for Southend Chalkwell Beach holiday rentals