Long Island holiday lettings

We found 544 holiday rentals — enter your dates for availability

Discover a selection of 7 homes and other holiday rentals in Long Island that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a TV. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Long Island

Showing deals for:24 Apr - 1 May

Image gallery for Sunny Spot with Private Parking.

Living area
9.8 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)

Sunny Spot with Private Parking.

South Portland

8% off
Price is £833
for 7 nights, 1 apartment
£119 per night
includes taxes & fees
Sunny Spot with Private Parking.

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Why visit Long Island

  • Pristine Beaches: Long Island boasts beautiful beaches, perfect for sunbathing and relaxation.
  • Historic Lighthouses: Explore charming lighthouses that reflect the island's maritime heritage.
  • Scenic Accommodations: Enjoy a range of holiday rentals, from quaint cottages to modern condos.
  • Welcoming Community: Experience the warmth of friendly locals and the rich local culture.
  • Outdoor Activities: Engage in various outdoor pursuits, ideal for families and solo adventurers alike.

Popular types of accommodation in Long Island

Planning a getaway to Long Island? The excitement begins with selecting the perfect accommodation. Discover a variety of holiday rentals, from charming cottages and spacious houses to modern condos. Whether you're seeking a tranquil retreat or a vibrant stay by the beach, Long Island offers an array of holiday lettings to suit every traveller's needs. Explore your options for unforgettable holiday homes and enjoy a delightful escape.

  • Houses: The top choice for visitors to Long Island, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: These delightful, quaint dwellings provide a charming atmosphere for a peaceful getaway.
  • Condos: A practical option that combines modern amenities with convenient locations, perfect for short or extended stays.
  • Apartments: Offering flexibility and independence, these rentals are suitable for couples and solo travellers alike.
  • Cabins: Embrace the great outdoors with a rustic cabin retreat, perfect for those seeking nature and tranquillity.**

Top attractions near Long Island

Long Island, Maine, offers a delightful escape for those keen on outdoor activities and scenic beach holidays. Visitors can explore beautiful beaches, historic lighthouses, and charming houses that reflect the local culture. Ideal for sightseeing, this destination caters to travellers seeking a blend of culture and outdoor experiences. Whether you're with family or exploring solo, Long Island promises a relaxing yet enriching holiday experience.

  • Portland Head Light: A historic lighthouse steeped in maritime culture, the Portland Head Light offers stunning coastal views and a glimpse into the region's rich nautical history. Located 3.1km from Long Island, it's a perfect spot for photography and exploration.
  • East End Beach: Just 2.5km away from Long Island, East End Beach is a picturesque stretch of sand ideal for sunbathing, swimming, and relaxing by the Atlantic. The beach vibes create a serene atmosphere for families and visitors alike.
  • Cross Insurance Arena: This entertainment hub, located 3.1km from Long Island, hosts a variety of events including concerts and sports. The arena is perfect for family outings and enjoying lively performances in a vibrant atmosphere.

Things to do recommended for couples

For a romantic getaway on Long Island, enjoy a concert at Thompson's Point, indulge in luxury at the Portland Club, or embark on an adventurous day with water sports at Capt Lyman Stuart. Each experience offers a unique charm perfect for couples seeking unforgettable moments.

Things to do recommended for families

Families visiting Long Island, Maine, can enjoy a thrilling game at Hadlock Field, explore the stars at Portland Observatory, and unwind at Fort Williams Park, perfect for relaxation and wellness. These attractions offer a delightful mix of sports, entertainment, and outdoor fun for all ages.

Things to do recommended for groups

Explore the Maine Mall for a lively shopping experience, only 5.6km from Long Island. Enjoy a visit to the Lyric Music Theater, just 2.5km away, for a touch of culture and entertainment. Don’t miss the iconic LL Bean Flagship Store, located 7.5km from your base.

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

If you’re travelling with a group, family, pets, or planning an extended stay, it’s essential to apply the appropriate filters to suit your needs. Here are some helpful tips for booking with Vrbo.

  • Traveling to Long Island with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group activities. Thankfully, you can refine your search to include all these options and more on Vrbo.
  • Traveling to Long Island with young kids: Journeying with young children can be quite demanding. It's important to prioritise their comfort and safety, alongside ensuring there are suitable amenities for their age, such as 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 Long Island: For many, a family holiday feels incomplete without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Long Island: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding features such as a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Long Island

Long Island, Maine, offers a delightful blend of tranquil beaches and stunning natural scenery, perfect for a relaxing getaway. Whether you're seeking family-friendly activities, a romantic escape, or a business retreat, the vibrant atmosphere caters to all. Explore charming nearby neighbourhoods, indulge in holiday rentals, or unwind in picturesque villas overlooking Long Island Sound. With friendly locals and a rich culture, your visit promises unforgettable experiences amidst breathtaking coastal beauty.

  • Portland: Located a mere 2.5km from Long Island, Portland is a vibrant city known for its stunning outdoor spaces and family-friendly activities. Visitors can enjoy a variety of experiences, from exploring local theatres to indulging in shopping at the lively mall centre. The city's proximity to beautiful beaches and serene lakes makes it perfect for a day out in nature. Don't miss the chance to stroll along the waterfront, where the scenic views are simply breathtaking.
  • South Portland: Just 3.1km away from Long Island, South Portland offers a delightful mix of family-oriented and urban experiences. The city is home to key shopping centres and educational facilities, catering to both tourists and locals. With its inviting beaches and peaceful lakes, South Portland is ideal for a relaxing day spent with loved ones. Be sure to explore the vibrant local eateries and shops that contribute to the city's unique charm.
  • Peaks Island: Only 1.2km from Long Island, Peaks Island is a picturesque getaway that enchants visitors with its natural beauty and romantic atmosphere. This idyllic island is perfect for outdoor enthusiasts, offering recreational areas and scenic spots for relaxation. Explore the local history museum to learn about the island’s past, or unwind on its tranquil beaches. Peaks Island is a must-visit for anyone looking to escape the hustle and bustle of city life.

Best time to go to Long Island

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.6°F (-3.0°C)Light RainMostly SunnyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostly SunnyAverageSlightly Low
March33.8°F (1.0°C)Light RainMostly SunnyAverageSlightly Low
April43.7°F (6.5°C)Light RainMostly SunnyAverageAverage
May53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
June61.3°F (16.3°C)Light RainMostly SunnyHighSlightly High
July68.2°F (20.1°C)Light RainMostly SunnyHighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
September61.9°F (16.6°C)Light RainMostly SunnyAverageAverage
October52.3°F (11.3°C)Light RainMostly SunnyLowAverage
November41.7°F (5.4°C)Light RainMostly SunnyLowAverage
December33.4°F (0.8°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Moreover, booking a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits 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 dedicated space to plan new adventures, pick up from where you last paused, or manage your travel arrangements. You can easily find properties you've previously saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards feature, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Charming Long Island will entice you

The island views and surrounding scenery provide a peaceful ambience to your holiday home in Long Island. This romantic city attracts visitors thanks to its restaurants and shopping. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Long Island

Are you hoping to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Long Island a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Dunegrass Golf Club (15.7 mi / 25.3 km)
  • Pirate's Cove (15.8 mi / 25.4 km)
  • Land's End Gift Shop (8.8 mi / 14.1 km)
  • Aquaboggan Water Park (15 mi / 24.1 km)
  • Gilsland Farm Audubon Center (3.8 mi / 6.1 km)
  • Riverside Municipal Golf Course (7.3 mi / 11.7 km)

Exploring the natural features in Long Island

Whether you're an active traveller or just want to spend some time taking in the scenery, Long Island is a great place to spend some time outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Sand Beach (2.5 mi / 3.9 km)
  • East End Beach (3.6 mi / 5.8 km)
  • Eastern Promenade (3.7 mi / 6 km)
  • Willard Beach (3.9 mi / 6.3 km)
  • Thompson's Point (6.5 mi / 10.4 km)
  • Casco Bay (8.8 mi / 14.2 km)

How to get to and around Long Island

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 7.4 mi (11.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 25.9 mi (41.6 km) away.

Frequently asked questions

What is the best area to stay in Long Island when booking a holiday rental?
When considering a holiday rental in Long Island, Maine, the best area to stay is near the village centre, where charm and convenience meet. This picturesque area boasts a selection of properties, ranging from quaint cottages to more spacious homes, allowing for a delightful range of options for visitors. Staying here puts you within easy reach of some of the island's top attractions, such as the scenic Long Island Lighthouse, which offers stunning views of the surrounding waters and is a fantastic spot for photography enthusiasts.
How much does it cost to rent a holiday home in Long Island?
Prices for holiday rentals in Long Island 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 Long Island 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 Long Island holiday house rentals?
You can find great discounts on house rentals in Long Island 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 Long Island?
For renting a beach house in Long Island, Maine, consider the picturesque coastline around the southern part of the island, particularly near the vibrant community surrounding the Long Island Town Landing. This area offers a selection of charming beach houses with stunning views of Casco Bay, many featuring amenities such as spacious decks, outdoor dining areas, and private access to the beach. These properties are great for families or groups looking to enjoy sun-soaked days by the water.

Additionally, the area near the Long Island Marina is another great option, where you can find rentals that often include features like fully equipped kitchens, laundry facilities, and sometimes even kayaks or paddleboards for guests to use. The nearby local shops and eateries add convenience for travellers seeking to enjoy fresh seafood and other local delicacies.
What is the most popular type of holiday rental accomodation in Long Island?
In Long Island, holiday houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties typically offer charming, homey interiors, often featuring multiple bedrooms, fully equipped kitchens, and inviting living spaces. Many rentals also provide outdoor amenities such as decks or patios, superb for enjoying the stunning coastal views and fresh sea air. Given the island's serene environment, these types of accommodations are ideal for families or groups seeking a peaceful getaway close to nature and the local attractions.
Are there any family house rentals in Long Island?
On Long Island, Maine, there are several family-friendly holiday rentals available, making it a delightful spot for groups seeking a coastal getaway. Many of these homes are located near the charming village area, where visitors can enjoy easy access to local shops and eateries. Properties typically feature spacious living areas, fully equipped kitchens for preparing family meals, and cosy outdoor spaces superb for gatherings or playtime for children.
Can I find long-stay holiday rentals in Long Island?
A long-stay holiday rental in Long Island 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 Long Island?
In Long Island, Maine, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these rentals are situated near the coastline, offering stunning views of the ocean and easy access to various outdoor activities. Expect amenities such as fully equipped kitchens, spacious living areas, and often outdoor spaces like decks or patios where pets can enjoy the fresh sea air.
Are there any remote work holiday rentals in Long Island?
In Long Island, Maine, there are several holiday rentals well-suited for remote work. These properties typically come equipped with essential amenities such as Wi-Fi and safe workspaces, allowing travellers to maintain productivity while enjoying the serene surroundings. The island's picturesque landscape offers a tranquil environment for those looking to balance work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Long Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Long Island 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 Long Island?
In Long Island, Maine, popular holiday rental amenities typically include kitchens, which are essential for self-catering during your stay. Many properties also feature patios where guests can enjoy the fresh coastal air and scenic views. Additionally, rentals often come equipped with cookware, dishware, and utensils, making it easy to prepare meals. Microwaves and ovens are also commonly available, enhancing the convenience for those looking to cook during their holiday.
When is the best time to visit Long Island for a holiday rental?
The best time to visit Long Island for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period draws travellers, eager to soak in the sun on stunning beaches and partake in various outdoor activities, such as kayaking and cycling along scenic coastal paths.

During the summer months, you can expect warm temperatures averaging in the low 20s Celsius, superb for enjoying beach picnics or exploring local shops and restaurants. The lively atmosphere is complemented by a variety of community events and festivals, making it an excellent choice for those who thrive in bustling environments.

For those who are mindful of their budget, visiting in November presents a wonderful opportunity. During this time, this off-peak month offers a chance to experience the serene beauty of the island with fewer crowds. You can enjoy peaceful walks along the shore and witness the stunning autumn hues as the landscape transitions.
How early should I book a Long Island holiday rental?
Book your Long Island 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 Long Island?
In Long Island, Maine, visitors can enjoy a range of attractions that showcase the area's natural beauty and charm. The picturesque waterfront is a major highlight, with opportunities for boating, fishing, and swimming. The Long Island Historical Society offers insights into the island's rich history, while the scenic trails provide superb spots for hiking and enjoying the coastal landscape.
Can I change or cancel my Long Island home rental booking on Vrbo?
To find Long Island 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Long Island 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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