Surfside vacation rentals

We found 900 vacation rentals — enter your dates for availability

Discover a selection of 19 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:May 1 - May 8

Image gallery for LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Exterior detail
10 out of 10, Exceptional, (178 reviews)
Exceptional
(178 reviews)

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Nantucket

8% off
Price is $598
$4,186 for 7 nights
All fees included
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

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Find out more about Surfside

Why visit Surfside

  • Beautiful Beaches: Surfside boasts stunning sandy beaches perfect for sunbathing, swimming, and relaxation.
  • Outdoor Activities: Enjoy a variety of outdoor adventures, from beachcombing to hiking in nearby trails.
  • Cultural Experiences: Visit local museums and libraries to immerse yourself in the rich cultural heritage of the area.
  • Charming Accommodations: Choose from cozy beach houses, cottages, and condos with breathtaking ocean views.
  • Local Cuisine: Don't miss the Surfside taco stand for delicious local treats during your stay.

Popular types of accommodation in Surfside

Surfside offers a variety of vacation rentals perfect for your getaway. Whether you’re looking for a cozy private vacation home, a charming cottage, or a modern condo, you'll find the ideal spot to unwind. Popular choices among travelers include Surfside beach houses that provide stunning ocean views. Don't forget to check out the local Surfside taco stand for a delicious treat during your stay. Choose your perfect Surfside rental and start making unforgettable memories.

  • Houses: The top choice for visitors to Surfside, offering spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A delightful option for those seeking a cozy and charming atmosphere, perfect for a romantic getaway or family retreat.
  • Condos: A popular selection that provides modern amenities and often stunning views, great for a convenient stay.
  • Apartments: A versatile choice for travelers, offering the comfort of home in a convenient location.
  • Cabins: A unique option for those wanting a rustic experience, surrounded by nature and tranquility.**

Top attractions in and around Surfside

Surfside, Massachusetts, is perfect for those seeking a beach getaway filled with stunning scenery and outdoor activities. Visitors can enjoy a mix of cultural experiences at local museums and libraries, while the beautiful beaches offer a relaxing escape. Whether you're traveling solo, with family, or as a couple, Surfside promises a delightful vacation rich in culture and coastal charm.

  • Surfside Beach: A picturesque beach known for its soft sand and inviting waves, perfect for sunbathing, swimming, and beachcombing. Enjoy the laid-back atmosphere, making it an ideal spot for families and relaxation.
  • Nantucket Atheneum: A charming library located 3 miles from Surfside, offering a rich collection of books and a cultural hub for families. Attend events and enjoy the beautiful architecture while exploring local history.
  • Whaling Museum: Situated 3 miles away, this museum immerses visitors in Nantucket's whaling history through engaging exhibits and artifacts, showcasing the island's maritime heritage and culture.

Things to do recommended for couples

Ready for a romantic getaway in Surfside? Enjoy a sailing adventure with Nantucket Community Sailing or hop on the Friendship Sloop Endeavor for a memorable day on the water. Both experiences are just 3 miles away, perfect for couples seeking outdoor excitement and togetherness.

Things to do recommended for families

Families visiting Surfside will love exploring the Vestal St Observatory and Loines Observatory, both just 3 miles away. These planetarium observatories offer exciting family-friendly experiences that combine education and entertainment, perfect for a fun day out with the kids.

Things to do recommended for groups

In Surfside, groups can enjoy a round of golf at Miacomet Golf Course, savor craft brews at Cisco Brewers, and catch a show at White Heron Theatre. Each venue offers a unique blend of outdoor fun, entertainment, and cultural experiences, perfect for an unforgettable group getaway.

*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 Surfside

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences in the search. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Surfside with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Surfside with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Surfside: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If you can relate, take a look at Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Surfside: If you’re in search of vacation rentals offering discounts for stays of a month or more, you’ve come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Surfside

Surfside, Massachusetts, is a charming village perfect for beach enthusiasts and outdoor adventurers. With its stunning sandy beaches and beautiful shorelines, visitors can enjoy serene surroundings while soaking up the sun. Nearby cities and neighborhoods offer exciting excursions, allowing travelers to immerse themselves in the local atmosphere. Whether you’re looking for relaxation or adventure, Surfside provides the ideal backdrop for an unforgettable vacation experience.

  • Nantucket: Nantucket is a picturesque island city that offers an idyllic blend of natural beauty and charming coastal culture. Located in the Atlantic Ocean, Surfside is situated within Nantucket, making it a perfect starting point for beach lovers and outdoor enthusiasts. Travelers flock to Nantucket for its stunning beaches, scenic landscapes, and opportunities for golfing. With local landmarks such as the family-friendly beaches and the breathtaking Cape, visitors can enjoy activities that range from relaxing on the sand to hitting the golf course. The island’s serene atmosphere and vibrant scenery make it a prime destination for a memorable vacation.
  • Nantucket Town: Just 3 miles from Surfside, Nantucket Town is a lively neighborhood brimming with charm and history. Visitors come here to experience the same beautiful beaches and outdoor scenery that Nantucket is famous for, while also enjoying a vibrant town atmosphere. The area features an array of popular activities, including golf and skiing, ensuring there's something for everyone. The picturesque beaches and family-friendly spots are perfect for a day out, while the local shops and dining options add to the town’s appeal. Nantucket Town truly embodies the spirit of coastal New England, making it a must-visit on your trip.
  • Naushop: Located 2 miles from Surfside, Naushop is a delightful neighborhood ideal for families and culture enthusiasts. This charming area offers a unique blend of outdoor experiences and cultural attractions, including theaters and local museums. Visitors can enjoy the beautiful beaches nearby, perfect for a day of sun and surf, or explore the local arts scene. Naushop’s family-friendly environment makes it a great destination for travelers looking to engage in wholesome activities while soaking in the rich culture of Nantucket. With its inviting atmosphere and proximity to Surfside, Naushop is a fantastic addition to your itinerary.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 some money on your upcoming trip? Being flexible with your travel dates can often lead to better prices, as they tend to vary. Additionally, if you book a longer stay, you might enjoy significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer truly has its perks. Enroll in our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the benefits.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for planning your travels, allowing you to start new trips, keep your existing plans on track, and manage your reservations effectively. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, simply visit: https://www.vrbo.com/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)
  • Jetties Beach (3.7 mi / 5.9 km)
  • Tom Nevers 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 best area to stay in Surfside when booking a vacation rental?
When planning a vacation in Surfside, Massachusetts, one of the best areas to consider for your rental is the charming neighborhood of Surfside Beach. This area offers a wonderful blend of serenity and accessibility, making it ideal for families and couples alike. The proximity to Surfside Beach itself is a major draw, as it boasts soft sands and gentle waves, superb for sunbathing, swimming, and beachcombing. Additionally, the nearby Nantucket Bike Path provides a scenic route for biking or walking, allowing you to explore the surrounding natural beauty.

Another appealing option is the area closer to the Nantucket town center. Staying here places you within easy reach of vibrant local shops, restaurants, and cultural attractions. You can stroll to the Whaling Museum, which showcases the rich maritime history of the area, or enjoy a meal at one of the many delightful eateries featuring fresh seafood.
How much does it cost to rent a vacation home in Surfside?
Prices for vacation rentals in Surfside 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 Surfside 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 Surfside vacation house rentals?
You can find great discounts on house rentals in Surfside 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.
Can I find long-stay vacation rentals in Surfside?
A long-stay vacation rental in Surfside is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Surfside vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Surfside with parking available—perfect for families or travelers 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.
How early should I book a Surfside vacation rental?
Book your Surfside vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Surfside?
In Surfside, Massachusetts, visitors can enjoy the beautiful beaches and serene atmosphere that the area offers. The nearby Surfside Beach is a top attraction, known for its soft sands and family-friendly environment, superb for swimming and sunbathing. Vacation rentals in this area often provide easy access to the beach, allowing for a relaxing seaside experience.

Additionally, the scenic bike paths and walking trails make it an ideal spot for outdoor enthusiasts. The proximity to the charming town of Nantucket, with its historic sites, shops, and restaurants, adds to the appeal.
Can I change or cancel my Surfside home rental booking on Vrbo?
To find Surfside vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Surfside vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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