Vacation rentals in Southend-on-Sea

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Top-rated vacation rentals in Southend-on-Sea

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Top guest favorite
A well-maintained garden is framed by lush greenery, showcasing vibrant flower beds and neatly trimmed hedges. Beyond the garden, expansive views of rolling hills and the Darent Valley can be seen under a partly cloudy sky.
Condo in Otford
4.99 out of 5 average rating, 141 reviews

Stunning Views over Garden & Valley

Wake up & lift the automatic blinds directly from your SUPER KING SIZE BED & be captivated by the VIEW of the beautiful Darent Valley unfolding before you through the picture windows. SNUGGLE in a cosy armchair with a book, listen to your favourite music or EXPLORE many footpaths along the valley. Stroll through the fields to Otford & Shoreham villages, visit HISTORIC HOUSES & vineyards or simply stay at home & enjoy a spacious studio apartment whilst staring at the sunset with a glass of wine

Top guest favorite
A comfortable double bed is featured with crisp white linens and a decorative cushion. Natural light filters in through patio doors, revealing a garden view filled with colorful flowers and greenery.
Guest suite in Southend-on-Sea
4.92 out of 5 average rating, 581 reviews

Quiet & Cosy Annex, Garden Outlook

Clean & bright 'Ground Floor Annex'; double room & separate en-suite area, 'The Annex' has a lovely garden outlook & its own entrance. Guests have the privacy of 'The Annex' (Adjoined - Guest Suite) with its own entrance to come-&-go as and when they please. A short distance to Southend Airport & Railway links to London. Explore the area - Southend Seafront, Pier & Town; Garons Festivals & Sports; Southends Events & Theatres . Early 'Check in' on request for Events, Weddings etc Relax & Enjoy !

Guest favorite
A light-filled living area contains two minimalist chairs with green cushions positioned around a glass table. Soft, flowing curtains frame the windows, and a small television is placed on a wooden console. Framed artwork rests nearby, contributing to a cozy ambiance.
Condo in Southend-on-Sea
4.93 out of 5 average rating, 30 reviews

Flat-on-Sea

Perfect location for convenience. The Flat is situated just moments from Airport, Hospital, Roots Hall Stadium and Priory Park. Prittlewell Station is just a 22-minute walk away, and with the A127 nearby, you're well-connected to the rest of Southend and beyond. There are plenty of food shops and restaurants nearby, offering everything from quick bites to sit-down meals. Whether you're visiting for business, leisure, or a quick stopover, our space combines comfort with unbeatable convenience.

Guest favorite
An open living space is showcased with light yellow walls and wood accents. A skylight above offers natural illumination. A comfortable chair and small desk are positioned near the window, while a cozy sleeping area with a quilted bedspread is visible in the background.
Guest suite in Southend-on-Sea
4.89 out of 5 average rating, 246 reviews

Light and Airy. En-suite with own private access.

Quiet open plan living space, one double bed. Separate shower room. Internet and SkyTV. Walking distance or 5 mins by car from train station into London via Southend Central station, bus route into town. 20 mins to Airport by car. Interesting country walks along Essex creeks and shore. Good food outlets and supermarket 3 mins away. Mini kitchen. Sitting area in garden. Well controlled pet welcome. Ideal for business trips and quiet getaways. Unrestricted free parking in the street.

Top guest favorite
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, 392 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.

Top guest favorite
A contemporary living space features a light green accent wall, complemented by dark furniture. A round table with wooden chairs is positioned next to a cozy seating area. Access to the outdoor space is provided through glass doors, enhancing the airy feel of the room.
Guesthouse in Essex
4.93 out of 5 average rating, 169 reviews

The secret hideaway (SS6)

Check-in is from 4pm. Check-out is by 10.00am. Early check in available for supplement as is check out. The Secret Hideaway is a self contained living space. Make use of the cooker to prepare a meal or relax watching your latest TV series. The bathroom is fully equipped with a power shower and is stylishly decorated with light grey tiles and white brickettes. Enjoy the comfort of a double bedroom equipped with bedside stylish cabinets and a clothes rail. Close to the A127.

Top guest favorite
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.
Apartment in Southend-on-Sea
4.99 out of 5 average rating, 145 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.

Top guest favorite
Condo in Southend-on-Sea
4.99 out of 5 average rating, 260 reviews

Thorpe bay beach deluxe apartment

Seashells is a beautiful seafront apartment with amazing views over the Estuary. Sit back and watch the ships sail past or cross the road and you are on the beach. We are a short stroll from the main strip on Southend seafront but far enough away to avoid the crowds. There are plenty of bars and restaurants within walking distance. The 1 bedroom apartment has a king size bed, south facing balcony, full kitchen, modern shower room, 50" tv and free wifi.

Top guest favorite
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
4.9 out of 5 average rating, 178 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.

Guest favorite
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
4.87 out of 5 average rating, 92 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 favorite
A spacious corner sofa with plush cushions is positioned in the living room, featuring a mix of grey and turquoise tones. The light wooden flooring complements the minimalist decor. A framed landscape photograph is mounted on the wall, adding a touch of visual interest.
Condo in Southend-on-Sea
4.74 out of 5 average rating, 259 reviews

Spacious 1 Bed flat. 5 min walk to beach & town.

Newly decorated ,Spacious 1 bed apartment. Less than 5 minute walk to sea-front and town centre. Brand new fitted kitchen and Electric Shower. Dog friendly with green space, ideal for dog walking, on the corner of the road and Southchurch Hall Gardens less than a 10 minute walk. I live above so any issues can be dealt with quickly. Free parking available both off road and permit parking. A perfect base for a seafront holiday.

Guest favorite
Home in Southend-on-Sea
4.9 out of 5 average rating, 124 reviews

Elegant Luxury Wedge Shaped Beach House

Make some memories in this unique and family-friendly house. The wedge is a unique house set over 3 floors in the shape of a wedge! A modern and fully renovated property offering a stylish luxury home away from home. An excellent location only 30 seconds walk from the beach, 2 minutes from Adventure Island theme park and surrounded by many lovely restaurants. 2 double bedrooms and a double sofa bed allows up to 6 guests.

Popular amenities for Southend-on-Sea vacation rentals

When is the best time to visit Southend-on-Sea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,206 GYDG$24,669 GYDG$25,506 GYDG$27,387 GYDG$28,432 GYDG$28,223 GYDG$27,596 GYDG$28,851 GYDG$26,133 GYDG$25,087 GYDG$24,251 GYDG$25,087 GYD
Avg. temp5°C5°C7°C9°C12°C16°C18°C18°C15°C12°C8°C6°C

Frequently Asked Questions

  • How is the weather in Southend-on-Sea?

    Southend-on-Sea experiences a temperate maritime climate. Summers are typically warm and dry with temperatures averaging around 66°F (19°C), while winters are cooler and often see temperatures drop to around 39°F (4°C). Rainfall is relatively evenly distributed throughout the year.

  • What are some of the best things to do in Southend-on-Sea?

    In Southend-on-Sea, popular activities include strolling along the Southend Pier, exploring the Southend Central Museum and Planetarium, visiting the bountiful seafront gardens, or enjoying the thrill rides at Adventure Island. The town also boasts beautiful beaches perfect for a relaxing day by the sea.

  • What is the best time of year to visit Southend-on-Sea?

    Summer is the most popular time to visit Southend-on-Sea, particularly from June to August. During this period, the town hosts numerous events such as the Southend Carnival and the Village Green Arts & Music Festival, drawing visitors for their vibrant displays and performances.

  • What are the best places to stay in Southend-on-Sea?

    Popular areas to stay in Southend-on-Sea include the central City Centre, known for its lively atmosphere and proximity to attractions, and the tranquil Thorpe Bay, admired for its grand houses and beautiful beachfront. Westcliff-on-Sea is also a favoured spot, with its mix of culture, dining, and shopping.

  • What are the best places to visit in Southend-on-Sea?

    Visitors to Southend-on-Sea often enjoy the Southend Pier, the world's longest pleasure pier, the vibrant Sea-Life Adventure aquarium, and the beautiful Prittlewell Priory, a historic house set in picturesque gardens. The Beecroft Art Gallery and Southchurch Hall are also frequently suggested locations.

  • What are some hiking trails in Southend-on-Sea?

    Southend-on-Sea is home to several scenic hiking trails. The Thames Estuary Path, which takes you along the estuary's edge, and the Prittle Brook Greenway, with its lush greenery and water views, are frequently suggested for their natural beauty.

  • What are some family activities to do in Southend-on-Sea?

    Southend-on-Sea has many family-friendly activities. Explore the educational Adventure Island theme park, enjoy marine life at Sea-Life Adventure, visit the Southend Pier Museum, or have a relaxing day at one of the sandy beaches such as Jubilee Beach or Three Shells Beach.

  • What are some of the best day trip ideas in Southend-on-Sea?

    Day trips from Southend-on-Sea can include visiting the historic town of Colchester 50 miles (80 km) away, exploring the lively seaside resort of Clacton-on-Sea 40 miles (64 km) away, or discovering the natural beauty of Epping Forest about 27 miles (43 km) away.

  • Are there family-friendly condo rentals in Southend-on-Sea?

    Southend-on-Sea has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there serviced apartment rentals with a dedicated workspace in Southend-on-Sea?

    Yes! Work meets play with ease at over 10 serviced apartment rentals in Southend-on-Sea featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about vacation rentals in Southend-on-Sea

  • Total vacation rentals

    Explore 480 vacation rentals in Southend-on-Sea

  • Nightly prices starting at

    Southend-on-Sea vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 16,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    170 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

  • Wi-Fi availability

    470 of Southend-on-Sea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Southend-on-Sea rentals

  • 4.7 Average rating

    Southend-on-Sea stays receive an average rating of 4.7 out of 5 from guests

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