Surfside vacation rentals

We found 724 vacation rentals — enter your dates for availability

Discover a selection of 25 homes and other vacation rentals in Surfside that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the amenities you need and want, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Surfside

Showing deals for:Nov 7 - Nov 14
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Find out more about Surfside

Find out more about Surfside

Why visit Surfside

  1. Stunning Beaches: Enjoy the breathtaking views and relaxation at Surfside Beach, ideal for sunbathing and swimming.
  2. Outdoor Adventures: Engage in various activities like surfing, hiking, and exploring the beautiful coastline.
  3. Charming Local Culture: Discover the vibrant community through local museums, churches, and quaint shops.
  4. Variety of Accommodations: Choose from beachfront rentals, cozy cottages, or modern condos for a memorable stay.
  5. Scenic Neighborhoods: Explore surrounding areas to immerse yourself in the local atmosphere and lifestyle.

Popular types of accommodation in Surfside

If you’re exploring vacation rentals in Surfside, you're in for a treat! Our most popular choices include Houses, charming Cottages, and modern Condos. Whether you’re looking for Surfside beach rentals or a cozy Surfside lodge, we provide transparent information to help you make the best choice. Trust us to connect you with the ideal Surfside realty for your getaway!

  • Houses: The top choice for visitors in Surfside, offering spacious and comfortable options for families, friends, or couples seeking a home-like atmosphere.
  • Cottages: A charming and cozy option, perfect for those wanting a quaint retreat close to the beach.
  • Condos: Ideal for those who appreciate modern amenities and a central location, making it easy to explore Surfside.
  • Apartments: A practical choice for solo travellers or couples, providing convenience and flexibility for your stay.
  • Cabins: A rustic option for nature lovers looking to immerse themselves in Surfside’s serene surroundings.**

Top attractions in Surfside

Surfside, Massachusetts, is perfect for a beach getaway, offering stunning scenery and outdoor adventures. Visitors can explore local attractions like the beach, museums, and churches, catering to those seeking culture, romance, and relaxation. For a memorable stay, consider beachfront rentals and joining a surf club. Make the most of your vacation by enjoying Surfside's beautiful coastline and vibrant community.

  1. Surfside Beach: This beautiful beach offers stunning ocean views and a relaxed vibe, perfect for sunbathing, swimming, and beachcombing. Enjoy the soft sand and gentle waves, making it an ideal spot for families and friends to unwind.
  2. Whaling Museum: Located 4.8km from Surfside, this fascinating museum showcases the rich history and culture of whaling in the region. Explore engaging exhibits that bring to life the maritime heritage of Nantucket.
  3. Nantucket Atheneum: Also 4.8km away, this charming library is a cultural hub, offering a welcoming environment for families. Enjoy a diverse collection of books and participate in community events that celebrate local arts and history.

Things to do recommended for couples

Planning a romantic getaway in Surfside? Enjoy a thrilling sailing experience with Nantucket Community Sailing or the Friendship Sloop Endeavor, both just 4.8km away. For a touch of luxury, visit the Sankaty Head Golf Club, located 11.3km from Surfside, perfect for a memorable couples' day out.

Things to do recommended for families

Families visiting Surfside can explore the fascinating Vestal St Observatory and Loines Observatory, both located 4.8km away. These planetariums offer engaging experiences with a family-friendly atmosphere, perfect for curious minds eager to learn about the stars and space.

Things to do recommended for groups

Enjoy a round of golf at Miacomet Golf Course, just 3.2km from Surfside. Experience local brews at Cisco Brewers, 4.8km away, perfect for relaxation. Don’t miss a show at White Heron Theatre, also 4.8km away, offering a delightful mix of culture and entertainment for the whole group.

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

When planning your travel, whether you're with a group, family, bringing along your pets, or seeking extended stays, it's important to use filters that align with your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Surfside with a group: Think about how many bedrooms you will require, as well as features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Surfside with young kids: Traveling with young children can present its own set of challenges. It’s important to prioritize their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, thinking about your closeness to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Surfside: For many families, a getaway isn’t truly fulfilling without their furry companion by their side. If you can relate, explore the Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Surfside: If you're seeking vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Surfside

Surfside, Massachusetts, offers a delightful beach getaway with its stunning Surfside Beach and oceanfront vacation spots. This charming village is perfect for those seeking scenic views and outdoor adventures. Explore the nearby neighborhoods to immerse yourself in the local atmosphere, making the most of your beachfront location. Whether you're lounging on the sand or embarking on excursions, Surfside promises an unforgettable experience for every traveller.

  • Nantucket Town: Located 4.8km from Surfside, Nantucket Town is a charming neighborhood that captivates visitors with its beautiful beaches and scenic outdoor spaces. Known for its rich maritime history, this area offers a delightful mix of activities, including golfing and skiing in nearby fields. Explore the stunning local landmarks, such as the family-friendly beaches and picturesque Cape Cod scenery, perfect for a relaxing day in the sun or a leisurely stroll along the shore.
  • West of Town: Also situated 4.8km away from Surfside, West of Town is a quaint village that shares a similar allure with its beach and outdoor experiences. This area is ideal for golf enthusiasts and offers access to a planetarium observatory for those curious about the stars. Visitors can enjoy the local beaches, including family-oriented spots, while taking in the breathtaking coastal views that make this region a must-see destination.
  • Naushop: Just 3.2km from Surfside, Naushop is a neighbourhood that focuses on outdoor activities, family fun, and cultural experiences. This vibrant area features a theatre and golf course, providing entertainment for all ages. Nearby attractions such as beaches and museums add to Naushop's appeal, making it a wonderful place to immerse yourself in local culture and create memorable family moments.

Best time to go to Surfside

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January36.9°F (2.7°C)Light RainMostly CloudyLowModerately Low
February36.5°F (2.5°C)Light RainMostly CloudyLowModerately Low
March39.2°F (4.0°C)Light RainMostly SunnyLowModerately Low
April45.9°F (7.7°C)Light RainMostly SunnyAverageAverage
May53.1°F (11.7°C)Light RainMostly SunnyAverageAverage
June61.3°F (16.3°C)Light RainMostly SunnyHighModerately High
July69.4°F (20.8°C)Light RainMostly SunnyHighModerately High
August70.7°F (21.5°C)Light RainMostly SunnyHighModerately High
September66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
October59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnyAverageAverage
December43.0°F (6.1°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Flexibility with your travel dates can often lead to significant savings, as prices can vary. Additionally, opting for a longer stay typically allows for greater discounts. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow your search by price, location, and type of vacation rental. We're here to help you find the best options for your travel needs.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides you with a convenient platform to plan new trips, refine your existing itineraries, or manage your bookings. Your saved or reserved properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Surfside getaway

Learn about the unique charm of Surfside with a stay in a private vacation home. This city has something for everyone. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Surfside

Are you hoping to find things to do while you're in the area? Venture out of your vacation home and experience everything that makes Surfside a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Miacomet Golf Course (2 mi / 3.2 km)
  • Siasconset Golf Course (5.7 mi / 9.2 km)
  • Nantucket Golf Club (5.6 mi / 9 km)

Exploring the natural landscape of Surfside

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Surfside is a great place to get out in nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Surfside Beach (0.3 mi / 0.4 km)
  • Nobadeer Beach (0.4 mi / 0.7 km)
  • Children's Beach (3 mi / 4.8 km)
  • Cisco Beach (3.4 mi / 5.4 km)
  • Hummock Pond (3.4 mi / 5.5 km)
  • Jetties Beach (3.7 mi / 5.9 km)

Transportation options to and around Surfside

Fly into Nantucket, MA (ACK-Nantucket Memorial), the closest airport, located 1.5 mi (2.4 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Vineyard Haven, MA (MVY-Martha's Vineyard), which is 29 mi (46.6 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Surfside?
Houses are the most popular kind of vacation rental in Surfside, according to our data. Even if you've got something bigger or smaller in mind, Vrbo has properties in a variety of sizes and shapes. Compare our options to find your perfect fit.
How much does it cost to rent a vacation rental in Surfside?
Length of stay, property type and season are among the factors that can influence the price of a vacation home. Simply add your dates of travel to find your perfect match. From comfy cottages to plush villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Surfside?
Prices for beach houses in Surfside will vary depending on the size and style of the property and time of year you're traveling. Simply enter your dates of travel into Vrbo and how many guests to see your rental options and prices. From there you can use our filter tool to refine your search by nearby activities, ratings, amenities and more.
Are there pet-friendly vacation rentals in Surfside?
With 25 vacation rentals that welcome pets, your little buddy can also come along on your Surfside getaway. Use our filter tool to search our pet-friendly vacation rentals and find a stay that's pawfect on Vrbo.
Can I rent a house with a pool in Surfside?
Grab your swimwear and pool noodle, because there are 10 houses with a private pool in Surfside. Stay at one of these sought-after vacation homes and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Surfside?
When it comes to rental amenities that guests are on the lookout for in Surfside, a firepit, a nearby waterfront and a garden are at the top of the list. With Vrbo vacation rentals, you'll enjoy options to match your style and taste, whether you're traveling with family members, friends or even pets.
Are there large group vacation rentals in Surfside?
Surfside has 10 vacation homes that can host 10 or more people. These stays come with all the space you need to share good times with friends and family.
Are there vacation rentals in Surfside that welcome kids?
Surfside has 25 family-friendly vacation homes to choose from. And finding a stay that welcomes kiddos is a cinch with our "Properties good for families" filter. Besides having the entire place to yourselves, you can also look forward to amenities and perks such as multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Surfside?
Keeping the kids amused during your vacation in Surfside is child's play with these cool family-friendly attractions:

  • Surfside Beach
  • Cisco Beach
  • Jetties Beach

Are there vacation rentals with WiFi in Surfside?
Surfside has nine vacation rentals with WiFi, so you'll be able to stay connected while traveling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to scrolling social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Surfside?
You'll have a choice of 19 vacation rentals with air conditioning in Surfside giving you that gentle, cool breeze and extra level of comfort. Simply enter your chosen travel dates and then use our handy filters to help you locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Surfside?
The minimum age allowed can differ between properties on Vrbo, so be sure to look at the rules of the vacation home in Surfside you want to book. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Surfside for?
The amount of time you can rent a Surfside vacation home for varies depending on the property. Just tap in your preferred travel dates to see available options that offer long-term stays. They come with everything you need to make your extended trip more comfortable and convenient, such as kitchens and laundries. Some vacation homes may also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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