A Gothic-style church with a tall steeple, large arched windows, and a clock tower.

Southport holiday rentals

We found 318 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Southport to find one that's 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.

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Find the best place to stay - Southport

Premier Host

Westport "Gold Coast" across from Southport beach

Sleeps 3 · 1 bedroom · 1 bathroom

4 BR Classic Country House in CT

Sleeps 8 · 4 bedrooms · 4+ bathrooms

Premier Host

Stareway to Heaven Su

Sleeps 8 · 4 bedrooms · 3+ bathrooms

Southport Shoreline Charm: Elegant Coastal Escape

Sleeps 7 · 3 bedrooms · 2 bathrooms

Southport Charm! Steps away from town!

Sleeps 6 · 4 bedrooms · 3 bathrooms

DUNE Fairfield Beach

Sleeps 3 · 1 bedroom

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Enjoy full kitchens, laundry, pools, gardens and more
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Why visit Southport

Charming Beaches: Southport Beach offers sunlit days and serene coastal views, perfect for relaxation and family outings.
Scenic Waterfront Walks: Explore picturesque waterfront paths that showcase the area's natural beauty and maritime heritage.
Cultural Attractions: Engage with local history and art at various museums and cultural sites throughout the town.
Gold Coast Allure: Discover the unique charm of Southport's affluent neighbourhoods and their stunning architecture.
Family-Friendly Atmosphere: Southport provides a welcoming environment for families, ensuring enjoyable experiences for all ages.

Popular types of accommodation in Southport

If you are unsure what type of accommodation you can expect in Southport, we have you covered. These are the most popular types of accommodation here, including Private Holiday Homes, Apartments and Cottages. Southport, Connecticut, offers a charming coastal experience with a rich maritime history, beautiful beaches, and scenic waterfront walks. Explore local attractions, landmarks and cultural experiences that make Southport a delightful destination for your next holiday rental adventure.

Private Holiday Homes: Enjoy the charm of secluded, self-catered retreats perfect for a peaceful stay in Southport.
Apartments: Experience city-style living in modern, fully-equipped urban flats ideal for short breaks.
Cottages: Delight in cosy, characterful dwellings offering a traditional escape in a quintessential setting.
Condos: Indulge in contemporary comfort with stylish, well-appointed units suited for relaxed getaways.
Villas: Revel in the spacious luxury of elegant, private residences perfect for a leisurely holiday in Southport.**

Top attractions near Southport

Southport, Connecticut, offers a delightful mix of outdoor and urban experiences. Visitors can explore its charming beaches, expansive urban parks, and engaging museums, all providing a taste of local culture and history. Ideal for families and culture enthusiasts alike, this picturesque city promises a blend of scenic beauty and cultural richness, ensuring a memorable holiday experience.

Fairfield Beach: Bask in the beach vibes of this relaxing shore, located 3km away, offering sandy stretches and refreshing sea air for a tranquil coastal experience.
Bridgeport Downtown South Historic District: Immerse yourself in the rich cultural tapestry of this historic village, located 10km away, where heritage and art blend to create a unique urban charm.
Silver Sands State Park: Enjoy outdoor adventures in this scenic national state park, located 19km away, offering picturesque landscapes and ample opportunities for active pursuits.

Things to do recommended for couples

Southport offers a charming seaside escape for couples. Enjoy a leisurely stroll along the picturesque beach or indulge in a romantic dinner at a waterfront restaurant. Don't miss the enchanting sunsets that paint the sky, creating the perfect backdrop for a memorable evening together.

Things to do recommended for families

Families will delight in exploring the scenic Southport Beach with its sandy shores and calm waters, perfect for swimming and picnicking. The charming Southport Village offers quaint shops and eateries, while the nearby Pequot Library hosts engaging children's programmes and events throughout the year.

Things to do recommended for groups

Experience thrills at The Adventure Park at Discovery Museum, a zipline and ropes course located 10km from Southport. Enjoy the fresh air and outdoor vibes as you tackle exciting challenges with your group, making unforgettable memories together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're planning a trip with a group, family, pets, or are seeking extended stays, it's essential to refine your search based on your specific needs. Here are some helpful booking tips for using Stayz.

Traveling to Southport with a group: Consider how many bedrooms you require, along with features such as a fully equipped kitchen or an outdoor area for group gatherings. Luckily, you can refine your search for these, and many other specifications, on Stayz.
Traveling to Southport with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, alongside 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 isn't truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
Planning for a long term stay visiting Southport: If you're in search of holiday rentals that offer discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Southport

Southport offers a delightful blend of outdoor and city charms. Enjoy sunlit days at Southport Beach, explore the Gold Coast’s allure, and savour the unique vibe of the Southport Campus. The region’s family-friendly and business atmospheres create a captivating backdrop for a memorable getaway, enriched by the unmistakable charm of Southport.

Fairfield: Fairfield is a vibrant city located 2km from Southport. It offers a dynamic mix of urban charm and outdoor leisure, where visitors enjoy a blend of city-themed and culture-themed experiences. The area boasts educational institutions, a well-maintained golf course, and expansive recreational areas. Notable attractions include a modern college university, a pristine beach and a family-friendly beach, making this locale an appealing destination for a well-rounded holiday.
Stamford: Stamford is a bustling city situated 23km from Southport. It is renowned for its family-friendly atmosphere and city-themed experiences, complemented by outdoor adventures. Travellers can explore a variety of shopping areas, enjoy theatrical performances and visit educational venues. Prominent local landmarks include a vibrant tourist precinct, a charming square and a modern square, ensuring that visitors have a diverse range of attractions to explore.
Norwalk: Norwalk, located 11km from Southport, is celebrated for its family-friendly and city-themed charm, paired with outdoor leisure options. The city offers access to educational facilities, shopping areas and a golf course, making it a versatile destination. Among its local highlights are a delightful beach, a modern college university and another family beach, providing a rich array of experiences for those keen to explore the area.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	31.6°F (-0.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	32.9°F (0.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	39.2°F (4.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	49.3°F (9.6°C)	Light Rain	Mostly Sunny	Average	Average
May	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Average
June	68.2°F (20.1°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	75.4°F (24.1°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	74.1°F (23.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	57.6°F (14.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	46.2°F (7.9°C)	Light Rain	Mostly Sunny	Average	Average
December	38.3°F (3.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Booking with Stayz is a breeze

Searching for ways to cut costs on your upcoming journey? Embracing flexibility with your travel dates might prove beneficial, as fares often fluctuate. Additionally, you can achieve considerable savings by opting for an extended stay. To find a Stayz property that meets your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides a dedicated space to initiate new journeys, continue your travel plans, or review and organise your bookings. Properties you have saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.stayz.com.au/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:

Country Club of Fairfield (0.8 mi / 1.3 km)
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)
Hand & Stone Massage and Facial Spa (14.5 mi / 23.4 km)
Del Vino Vineyards (15.6 mi / 25.2 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:

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)
Seaside Beach (4.5 mi / 7.2 km)
Seaside Park (4.8 mi / 7.7 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, the charming neighbourhood of Southport Beach stands out as an excellent choice. This picturesque area boasts a beautiful sandy beach, great for sunbathing and leisurely strolls along the shoreline. Visitors can enjoy stunning views of Long Island Sound and take advantage of the nearby Southport Harbour, which is a lovely spot for boating and sailing enthusiasts.Another appealing area is the historic district, where you'll find quaint streets lined with lovely historic-style homes and vibrant local shops. This area is home to the iconic Southport Congregational Church, which adds to the neighbourhood's charm. In addition, the picturesque landscapes of the Southport Golf Club provide a serene backdrop for those who appreciate a bit of greenery.In terms of holiday rentals, Southport offers a diverse selection of properties ranging from cosy cottages to elegant waterfront homes, suiting a variety of preferences.

Where are the best areas for renting a beach house in Southport?

For renting a beach house in Southport, travellers should consider the picturesque areas along the Long Island Sound. The neighbourhoods of Southport and nearby Fairfield offer charming coastal homes with easy access to sandy beaches and scenic waterfront views. Many properties in this vicinity come equipped with amenities such as private decks, outdoor grilling areas, and spacious gardens, making them ideal for families or groups eager to enjoy outdoor living by the sea.The Southport Beach area is particularly popular, where rentals often feature easy access to the beach and stunning sunsets over the water. Properties here frequently include modern kitchens, comfortable living spaces, and some even provide bicycles for exploring the nearby coastal paths.In addition, the nearby Fairfield town offers additional options, with its vibrant downtown area and local shops and restaurants adding convenience for visitors. Rentals in this area tend to be well-appointed, with many featuring amenities like air conditioning, Wi-Fi, and laundry facilities, ensuring a comfortable stay.

What is the most popular type of holiday rental accomodation in Southport?

In Southport, holiday houses are the most popular type of holiday rental, with around 12 available throughout the area. These homes are typically situated in charming neighbourhoods, offering a spacious environment ideal for families or groups. Most holiday houses come with fully equipped kitchens, comfortable living areas, and outdoor spaces for relaxation. In addition to these, there are several cottages that provide a cozier, more intimate setting, often featuring rustic decor and gardens.

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 groups seeking a coastal retreat. The area is known for its charming neighbourhoods and proximity to picturesque beaches. Properties often feature spacious living rooms, fully equipped kitchens for family meals, and outdoor areas where children can play or relax.Visitors can explore nearby attractions such as the scenic Southport Beach, great for sunny days, and the beautiful Southport Historic District, where local shops and eateries can be found. Additionally, many rentals come with amenities like Wi-Fi and air conditioning, ensuring a comfortable stay for families.

Are there pet-friendly house rentals in Southport?

In Southport, there are several pet-friendly house rentals available, great for travellers looking to enjoy a charming coastal community. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.The neighbourhood itself offers a picturesque setting with easy access to local parks and the stunning waterfront. Nearby, the beautiful Southport Beach provides a lovely spot for walks with your furry companions. Additionally, the area features pet-friendly cafes and shops that welcome four-legged visitors, enhancing the overall experience for pet owners.

Are there any remote work holiday rentals in Southport?

In Southport, Connecticut, there are several holiday rentals suitable for remote work, with around 12 options available. This charming coastal town offers a serene atmosphere, making it an ideal setting for those looking to balance work and leisure. Many of these properties feature essential amenities such as high-speed Wi-Fi, comfortable workspaces, and inviting living areas that allow for productivity during your stay.Travellers can expect to find a mix of charming cottages and more spacious homes, often equipped with full kitchens for convenient meal preparation and outdoor spaces for relaxation after a long day of work. Southport's picturesque surroundings, including its lovely beaches and quaint shops, provide plenty of opportunities for breaks and exploration. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.

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, and air conditioning for comfort during warmer months. Many properties are also pet-friendly, making it easier for travellers to bring their furry companions along. Additional amenities often found in these rentals include blenders for making smoothies or cocktails, and coffee and tea makers to enjoy a warm beverage upon waking.

When is the best time to visit Southport for a holiday rental?

The best time to visit Southport for a holiday rental is during the peak season from July to September. This vibrant period is great for those seeking a quintessential New England summer experience, with warm temperatures averaging between 20 to 30 degrees Celsius. Visitors can indulge in outdoor activities such as sailing, beach days, and strolling along the scenic coastline, all while enjoying the charming atmosphere of this picturesque seaside town.July stands out as the most popular month, attracting families and leisure travellers eager to soak up the sun and engage in local festivals and events. The lively streets come alive with music, art, and delicious offerings from nearby restaurants, making it an excellent time for socialising and exploring.For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, averaging around 0 to 5 degrees Celsius, Southport's winter charm is undeniable. This quieter month allows for a peaceful retreat, great for enjoying cozy local cafes and festive holiday decorations without the summer crowds.

What are the top attractions in Southport?

In Southport, visitors can enjoy a blend of natural beauty and historic charm. The picturesque Southport Beach offers sandy shores and scenic views of Long Island Sound, making it a lovely spot for relaxation and seaside strolls. The nearby Pequot Library is a great cultural institution, renowned for its distinctive architecture and extensive collection of books and art, often hosting community events and exhibitions.For a taste of local history, the Southport Historic District features charming 19th-century buildings and the iconic Southport Railway Station, which adds to the area's quaint atmosphere. Additionally, the nearby Connecticut Audubon Society offers opportunities for birdwatching and enjoying nature trails, appealing to outdoor enthusiasts.

Are all fees included in the Southport holiday homes prices shown on Stayz?

Stayz 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.

Are there any Southport holiday homes with parking?

Stayz offers a wide selection of holiday homes 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 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.

Are there any discounts for Southport holiday homes?

You can find great discounts on holiday homes in Southport on Stayz, 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.

Can I change or cancel my Southport holiday home booking on Stayz?

To find Southport holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.

Can I find long-stay holiday homes in Southport?

A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Can I plan a group trip on Stayz?

Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.

How early should I book a Southport holiday home?

Book your Southport holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.

How much does it cost to rent a holiday home in Southport?

Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Southport to more spacious homes.

What can I expect from Stayz customer service and StayzCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

What is StayzCare™ and how does it work?

Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

Why should I join Stayz as a host?

Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.