Southport holiday lettings

We found 311 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Southport that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the amenities that you expect and more, such as Wi-Fi and cable TV. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Southport

Showing deals for:21 Nov - 28 Nov
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Southport

Find out more about Southport

Why visit Southport

  • Charming Beaches: Southport Beach offers sandy shores ideal for family outings or romantic strolls.
  • Outdoor Activities: Enjoy a variety of family-friendly outdoor adventures in urban parks and natural areas.
  • Welcoming Atmosphere: Experience the friendly local culture and pleasant weather throughout your visit.
  • Diverse Accommodation: Choose from private holiday homes, apartments, and cottages to suit your preferences.
  • Rich Local Culture: Immerse yourself in the unique charm and attractions of Southport's vibrant community.

Popular types of accommodation in Southport

If you're pondering the ideal accommodation for your getaway in Southport, look no further. Our most sought-after options include Houses, Apartments, and Cottages, ensuring there's something to suit every taste. Whether you're in search of holiday rentals, holiday lettings, or a charming holiday home rental, you'll find a variety of choices to make your stay memorable. Enjoy the comfort and convenience of our holiday accommodation options tailored just for you.

  • Houses: The top choice for visitors in Southport, offering spacious and comfortable living for families and groups.
  • Apartments: A popular option for those seeking a convenient and self-contained space during their stay.
  • Cottages: Charming and quaint, these rentals provide a homely feel, perfect for a relaxing getaway.
  • Condos: Ideal for those looking for modern amenities in a community setting.
  • Villas: Luxurious accommodations that offer privacy and upscale features for an indulgent holiday experience.**

Top attractions near Southport

Southport, Connecticut, is ideal for family-friendly outdoor holidays, offering a delightful mix of beach, urban parks, and modern college campuses. Visitors can immerse themselves in the local culture while enjoying various attractions that cater to outdoor enthusiasts and families alike. With its charming atmosphere, Southport promises a memorable experience for all types of travellers.

  • Fairfield University: A vibrant modern university just 1.2km from Southport, offering a lively atmosphere with beautiful campus architecture and a strong sense of community.
  • Jennings Beach: Located 1.2km away, this lovely beach features sandy shores and a relaxing vibe, perfect for sunbathing, swimming, or enjoying a leisurely stroll along the coastline.
  • Total Mortgage Arena: Situated 3.7km from Southport, this entertainment venue provides a fantastic family-friendly atmosphere, hosting a variety of events from concerts to sports.

Things to do recommended for couples

For a romantic getaway in Southport, don't miss a concert at Levitt Pavilion, just 2.5km away, or indulge in a wine tasting at Harmony Vineyards, 10.6km away. For adventure, try water sports at Waterski Connecticut, also 10.6km away. Enjoy your couple's retreat!

Things to do recommended for families

Families visiting Southport can enjoy an exciting day at the Hartford HealthCare Amphitheater, just 3.7km away, or relax at Seaside Park, 3.1km away. The Rolnick Observatory, 1.9km from Southport, offers a fascinating planetarium experience that the whole family will love.

Things to do recommended for groups

Groups visiting Southport can enjoy a captivating performance at the Fairfield Theater Company, indulge in a round of golf at the Pine Creek Par 3 Golf Course, or challenge themselves at the Fairchild Wheeler Golf Course, all while soaking up the local outdoor and cultural vibes.

What do I need to keep in mind when booking a vacation in 'Southport

If you're planning a trip with a group, your family, or even pets, or if you're interested in extended stays, be sure to refine your search based on your key preferences. Here are some helpful Vrbo booking suggestions for you.

  • Traveling to Southport with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for all these options and more on Vrbo.
  • Traveling to Southport with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, alongside providing suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Southport: For many, a family holiday wouldn’t feel complete without their furry companion. If you can relate to this, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Southport: If you’re seeking holiday rentals with discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Southport

Your holiday to Southport, Connecticut promises a delightful blend of outdoor adventures and city charm. Enjoy Southport Beach's sandy shores, perfect for family-friendly outings or a romantic stroll. Explore the surrounding areas, where friendly locals and sunny weather create a welcoming atmosphere for every traveller. Whether you're seeking a short-term holiday or an extended getaway, Southport and its nearby attractions offer a memorable experience for all types of visitors.

  • Stamford: Stamford is a vibrant city located 8.7km from Southport, offering a delightful blend of urban sophistication and family-friendly activities. Visitors can immerse themselves in a bustling shopping area, enjoy performances at local theatres, and explore educational venues. The city is known for its modern square and tourist precinct, providing a lively atmosphere for both residents and tourists alike. Outdoor enthusiasts will appreciate the parks and recreational spaces that invite leisurely strolls and picnics, making Stamford a well-rounded destination for all types of travellers.
  • Fairfield: just 1.6km from Southport, Fairfield is a charming city that caters to those seeking a mix of culture and outdoor enjoyment. With a strong emphasis on education, visitors can explore local colleges and universities while also taking advantage of its beautiful beaches. The family-friendly beach areas offer a perfect spot for relaxation and recreation, complemented by nearby shopping precincts. Fairfield's blend of city life and coastal charm makes it an ideal destination for families and culture enthusiasts alike.
  • Norwalk: Located 4.3km from Southport, Norwalk is a lively city that boasts a family-oriented atmosphere, outdoor activities, and a rich urban experience. Visitors can indulge in shopping, educational pursuits, and even winter sports like skiing. The city's attractions include beautiful beaches and historic sites that provide a glimpse into its past. Norwalk's diverse offerings ensure there's something for everyone, making it a must-visit for families and those looking to explore the best of Connecticut.

Best time to go to Southport

If you're planning a trip to Southport, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like October and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.6°F (-0.2°C)Light RainMostly SunnySlightly LowSlightly Low
February32.9°F (0.5°C)Light RainMostly SunnyAverageSlightly Low
March39.2°F (4.0°C)Light RainMostly SunnyAverageSlightly Low
April49.3°F (9.6°C)Light RainMostly SunnyAverageAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
June68.2°F (20.1°C)Light RainMostly SunnySlightly HighSlightly High
July75.4°F (24.1°C)Light RainMostly SunnySlightly HighSlightly High
August74.1°F (23.4°C)Light RainMostly SunnyAverageSlightly High
September67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
October57.6°F (14.2°C)Light RainMostly SunnySlightly LowAverage
November46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
December38.3°F (3.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay often results in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels, pick up where you last paused, or manage and organise your itineraries. You can easily access properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The lively city of Southport awaits you

The area's temples and opera are just some of the reasons to come on holiday to Southport. Renowned for its hockey games, beaches and restaurants, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Southport

Do you want to discover top things to see and do in the area? Venture out of your holiday home and experience everything that makes Southport a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Norwalk Maritime Aquarium (7.4 mi / 11.9 km)
  • Beardsley Zoo (7.4 mi / 11.9 km)
  • Chelsea Piers (13.4 mi / 21.5 km)
  • Great River Golf Club (14.2 mi / 22.8 km)
  • Del Vino Vineyards (15.6 mi / 25.2 km)
  • Country Club of Fairfield (0.8 mi / 1.3 km)

Exploring the natural features in Southport

Whether you're an active traveller or just want to spend some time taking in the scenery, Southport is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Southport Beach (1.1 mi / 1.7 km)
  • South Pine Creek Beach (1.3 mi / 2.2 km)
  • Fairfield Beach (1.8 mi / 2.8 km)
  • Penfield Beach (2.2 mi / 3.6 km)
  • Jennings Beach (2.4 mi / 3.9 km)
  • Compo Beach (4.3 mi / 6.9 km)

How to get to and around Southport

Fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), the closest airport, located 8.1 mi (13 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 19.4 mi (31.2 km) away.

If you're travelling by train, you can make your way to Southport Station.

Frequently asked questions

What is the best area to stay in Southport when booking a holiday rental?
When considering a holiday rental in Southport, Connecticut, a popular area to stay is the charming village of Southport itself. This picturesque neighbourhood boasts stunning views of the Long Island Sound and is known for its historic character, featuring beautiful historic architecture and quaint streets. A highlight of staying in Southport is the proximity to the Southport Beach, where visitors can enjoy sunbathing, swimming, or simply relaxing by the water.

Another attraction worth exploring is the Southport Harbor, which offers a delightful setting for leisurely walks and offers a glimpse into the maritime history of the area. The local shops and restaurants provide a lovely selection of dining options, great for enjoying a meal after a day of sightseeing.
How much does it cost to rent a holiday home in Southport?
Prices for holiday rentals in Southport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Southport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Southport holiday house rentals?
You can find great discounts on house rentals in Southport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Southport?
For renting a beach house in Southport, Connecticut, travellers should consider the picturesque waterfront along Southport Beach, which offers a serene setting with beautiful views of the Long Island Sound. Properties in this area often feature amenities such as spacious decks for outdoor dining, private gardens, and easy access to the sandy beach, making them superb for families looking to enjoy a relaxing seaside holiday.

Just a short stroll from the beach, the charming village centre of Southport provides a delightful mix of local shops and eateries, ideal for those who enjoy exploring quaint boutiques and sampling regional cuisine. Many holiday rentals in this neighbourhood come with modern conveniences like fully equipped kitchens, laundry facilities, and ample living space, ensuring a comfortable stay.
What is the most popular type of holiday rental accomodation in Southport?
In Southport, holiday houses and cottages are the most popular types of rental accommodations, with several available throughout the picturesque area. These properties often feature spacious living areas, fully equipped kitchens, and outdoor spaces such as gardens or patios, ideal for enjoying the pleasant coastal atmosphere. Many of the rentals are situated near the charming Southport Village, providing easy access to local shops, dining options, and the scenic waterfront.
Are there any family house rentals in Southport?
In Southport, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for families looking to enjoy a coastal getaway. This charming town features lovely properties that often include spacious living areas, well-equipped kitchens, and outdoor spaces where children can play safely. Many homes come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all.
Can I find long-stay holiday rentals in Southport?
A long-stay holiday rental in Southport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Southport?
In Southport, there are several pet-friendly house rentals available, offering a delightful mix of comfort and convenience for travellers with furry companions. Many of these holiday homes come equipped with modern amenities such as spacious kitchens, comfortable living areas, and outdoor spaces where pets can enjoy fresh air.
Are there any remote work holiday rentals in Southport?
In Southport, Connecticut, there are several holiday rentals available that cater to remote work needs. These properties often come equipped with essential amenities such as reliable Wi-Fi and dedicated workspaces, including desks, allowing for comfortable productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Southport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Southport with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Southport?
In Southport, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals with ease. Many rentals also feature coffee makers for a convenient morning brew, along with cookware, dishware, and utensils to cater to all dining needs. Additionally, dishwashers are commonly available, making clean-up after meals a straightforward experience.
When is the best time to visit Southport for a holiday rental?
The best time to book a holiday rental in Southport is during the peak season, which runs from July to September. This vibrant period draws beach lovers and families eager to soak up the sun on the sandy shores of Long Island Sound. With warm temperatures typically ranging from the mid-teens to low 30s Celsius, visitors can indulge in a variety of outdoor activities, from sailing to beach volleyball, all while enjoying the picturesque coastal scenery.

July is particularly popular, as it offers a lively atmosphere filled with events and bustling local markets. You'll find plenty of opportunities for sightseeing, such as visiting the beautiful Southport Beach or exploring the charming downtown area with its boutique shops and delightful eateries.

If you're looking for a more budget-friendly option, consider planning your visit in December. While this month is quieter, it brings a unique charm to Southport with festive decorations and holiday events, making it a lovely time for those who appreciate seasonal celebrations.
How early should I book a Southport holiday rental?
Book your Southport holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Southport?
In Southport, visitors can enjoy a charming coastal experience with several key attractions. The picturesque Southport Village is a delightful area to explore, featuring historic homes and scenic waterfront views. The Southport Harbor offers opportunities for boating and fishing, while the nearby Southport Beach is superb for a relaxing day by the sea.
Can I change or cancel my Southport home rental booking on Vrbo?
To find Southport holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Southport holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

More Holiday Rentals ideas

People also search for