Best Vacation Homes in Surfside
House
10.0(129 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
AU $1,044/Night
7 Nights - AU $7,306
Bed & Breakfast
10.0(29 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
AU $1,030/Night
7 Nights - AU $7,213
New
House
10.0(17 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
AU $1,325/Night
7 Nights - AU $9,277
House
9.8(6 Reviews)
2 Bedrooms
3 Baths
6 Guests
1603.82 ft²
Oceanfront- Breakfast
- Parking
Ocean View
AU $2,764/Night
7 Nights - AU $19,350
New
House
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
Child Friendly
AU $4,192/Night
7 Nights - AU $29,346
House
10.0(10 Reviews)
4 Bedrooms
4 Baths
8 Guests
2500 ft²
Private Pool- Oceanfront
- Parking
Pool
AU $2,375/Night
7 Nights - AU $16,626
New
Condo
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $1,120/Night
7 Nights - AU $7,839
Surfside Luxury Rentals
House
2 Bedrooms
3 Baths
4 Guests
4500 ft²
Hot Tub- Parking
- Pool
- Ocean View
AU $12,324/Night
7 Nights - AU $86,267
New
House
10.0(1 Review)
6 Bedrooms
7 Baths
13 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
AU $10,823/Night
7 Nights - AU $75,758
House
9.8(7 Reviews)
6 Bedrooms
7 Baths
12 Guests
- Pool
- Balcony/Terrace
- Child Friendly
Security/Safety
AU $9,387/Night
7 Nights - AU $65,710
House
10.0(53 Reviews)
8 Bedrooms
9 Baths
23 Guests
8300 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
AU $8,903/Night
7 Nights - AU $62,319
House
8 Bedrooms
7 Baths
16 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
AU $8,165/Night
7 Nights - AU $57,154
AU $8,039/Night
7 Nights - AU $56,272
House
10.0(4 Reviews)
4 Bedrooms
4 Baths
10 Guests
4070 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $7,486/Night
7 Nights - AU $52,404
New
House
6 Bedrooms
5 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $7,290/Night
7 Nights - AU $51,028
Surfside Pet Friendly Vacation Rentals
House
10.0(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $2,176/Night
7 Nights - AU $15,231
Bed & Breakfast
9.5(31 Reviews)
4 Bedrooms
4 Baths
10 Guests
360.59 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $865/Night
7 Nights - AU $6,053
House
9.8(51 Reviews)
5 Bedrooms
4 Baths
12 Guests
3500 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
AU $3,884/Night
7 Nights - AU $27,192
House
8.5(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1776.05 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
AU $1,899/Night
7 Nights - AU $13,294
New
Apartment
2 Bedrooms
1 Bath
3 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
AU $2,436/Night
7 Nights - AU $17,053
Cottage
10.0(299 Reviews)
1 Bedroom
1 Bath
4 Guests
920 ft²
- Oceanfront
- Parking
- Pool
Spa
AU $875/Night
7 Nights - AU $6,126
House
10.0(187 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Spa
AU $1,217/Night
7 Nights - AU $8,516
Cottage
10.0(130 Reviews)
1 Bedroom
1 Bath
2 Guests
1025 ft²
- Oceanfront
- Parking
- Pool
- Spa
AU $923/Night
7 Nights - AU $6,462
Surfside Large Vacation Homes
House
10.0(92 Reviews)
5 Bedrooms
2 Baths
11 Guests
1798 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $2,467/Night
7 Nights - AU $17,269
Bed & Breakfast
9.7(53 Reviews)
13 Bedrooms
13 Baths
26 Guests
231.84 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
AU $1,259/Night
7 Nights - AU $8,813
House
10.0(78 Reviews)
5 Bedrooms
5 Baths
14 Guests
4500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $3,303/Night
7 Nights - AU $23,119
Cabin
9.5(22 Reviews)
13 Bedrooms
13 Baths
28 Guests
245.91 ft²
- Oceanfront
- Breakfast
- Ocean View
- Balcony/Terrace
AU $600/Night
7 Nights - AU $4,201
House
10.0(77 Reviews)
4 Bedrooms
4 Baths
12 Guests
3326 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $2,010/Night
7 Nights - AU $14,072
Apartment
10.0(76 Reviews)
3 Bedrooms
1 Bath
10 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- View
AU $1,645/Night
7 Nights - AU $11,513
House
10.0(66 Reviews)
5 Bedrooms
8 Baths
14 Guests
5100 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $4,033/Night
7 Nights - AU $28,229
House
10.0(62 Reviews)
5 Bedrooms
5 Baths
10 Guests
4000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $3,758/Night
7 Nights - AU $26,307
Why Choose Rent By Owner for your Surfside Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Surfside
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when the area offers pleasant weather and fewer crowds, allowing you to fully enjoy this charming destination in Nantucket, Massachusetts.
Peak Season Highlights
Late Spring to Early Summer (May - June)
During this period, you can enjoy pleasant weather and fewer crowds, making it an ideal time for exploring the scenic coastal area with your vacation rentals.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Mid to Late Summer (July - August)
This is the busiest season when the area is vibrant with visitors, perfect for experiencing lively local events while staying in comfortable vacation rentals.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Off-Season Highlights
Early Fall (September - October)
The region offers cooler temperatures and tranquil surroundings, making it a great time to enjoy your vacation rental without the summer crowds.
Average Temperature Daytime: 60-70°F - Nighttime: 45-55°F
Late Winter to Early Spring (February - March)
Experience quieter beaches and serene landscapes during this time, ideal for those seeking a peaceful retreat in cozy vacation rentals.
Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
Weekly Weather Forecast for Surfside
How to Book Your Surfside Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Surfside
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas with picnic tables or grills for alfresco meals under the sun.
- Relax in landscaped gardens or lush lawns that offer peaceful outdoor spaces to unwind.
- Experience private or shared patios and decks perfect for entertaining or simply basking in the sunshine.
- Take advantage of outdoor showers or bathing areas, ideal for rinsing off after a day at the beach.
- Make use of spacious yards or open-air spaces for outdoor activities and family games.
- Benefit from access to nearby beaches or waterfronts, just steps from your rental to enjoy the region’s scenic coastlines.
- Utilize outdoor parking facilities to conveniently come and go during your stay in the area.
Top Attractions Around Surfside
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities such as relaxing on pristine beaches, exploring scenic walking trails, and engaging in watersports, all within close proximity to your ideal vacation rentals.
Family Activities
- Beach Day at Surfside Beach: Spend quality time with your family relaxing and playing on the sandy shores of Surfside Beach, a favorite destination for beach-loving visitors to Nantucket.
- Nantucket Historical Museum: Explore local history through engaging exhibits that offer insightful stories about the region’s rich maritime heritage, perfect for curious young minds and adults alike.
- Cliff Walks and Scenic Trails: Enjoy scenic walks along coastal trails with breathtaking views, providing a memorable experience for families seeking outdoor adventure in this area.
- Whale Watching Tours: Embark on an exciting whale watching excursion that brings families closer to the region’s famous marine wildlife, making for an unforgettable activity during your stay.
Adult Activities
- Beachcombing and Sunset Walks: Explore the pristine sands and enjoy spectacular sunsets along the shoreline, perfect for a relaxing evening in this coastal area.
- Fishing Charters and Water Activities: Embark on guided fishing excursions or try paddleboarding in the calm waters that surround this popular seaside destination.
- Dining at Local Seafood Restaurants: Indulge in fresh, locally-sourced seafood at nearby establishments known for their authentic flavors and oceanfront views.
- Exploring Nature Trails and Conservation Land: Discover scenic hiking and biking paths that wind through protected land, offering a peaceful escape into the region’s natural beauty.
Other Places to Stay in Surfside, MA
Surfside Beach
Nobadeer Beach
Surfside Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Peak Season: Book your Nantucket vacation rental in advance to secure the best options and rates during the busy summer months.
- Explore Local Beaches: Take advantage of the region's pristine beaches by visiting nearby surf spots and sandy shores to enjoy relaxing days by the water.
- Discover Authentic Dining: Savor the local cuisine at area restaurants that showcase fresh seafood and regional flavors unique to this coastal destination.
- Utilize Nearby Transportation: Make use of available bike rentals or shuttles within the area to easily explore the town and maximize your time here.
Transportation Options
- Ferries: You can easily reach this coastal area by ferry, offering scenic crossings from the mainland to Nantucket with stunning views of the region.
- Rental Cars: Renting a car provides flexibility for exploring locally and navigating the scenic roads surrounding Surfside in comfort and convenience.
- Taxi Services: Taxis are readily available here, providing quick and reliable transportation to nearby beaches, restaurants, and attractions on the island.
- Bicycle Rentals: Biking is a popular way to enjoy the area's natural beauty, with many rental shops offering bikes to explore the charming surroundings at your own pace.
Local Customs Options
- Respect for the Local Environment: Here, maintaining the pristine beauty of Nantucket's beaches and natural landscapes is a common courtesy among residents and visitors alike.
- Beach Etiquette: When enjoying the shore, it’s customary to leave no trace, ensuring that the scenic surroundings remain unspoiled for others to appreciate.
- Preserving Maritime Traditions: Engaging in or observing local maritime customs, such as traditional boat handling, reflects the area's deep-rooted seafaring heritage.
- Community Celebrations: Participating in local events like seasonal festivals showcases the region's friendly spirit and respect for its cultural traditions.
Frequently Asked Questions About Surfside?
1. What are the top vacation rentals in Surfside?
There are a lot of options in Surfside. If you plan on staying in the Surfside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Surfside:
- Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
- LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
- BEAUTIFUL COTTAGE on ORANGE ST, WALK TO MAIN STREET!
- Charming cottage, close to lower Main Street.
- Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
- Beautifully Renovated Main Street Cottage- Great Location
- A Literary Oasis In The Heart Of Nantucket Town
- Ten min. walk to Downtown. Perfect for families/groups. Aug. 22-29 available.
- In-Town Walk to Beaches Charming Cottage Private Patio & Easy Parking
- Historic 2 bedroom cottage in the heart of old town Nantucket
2. How many vacation rentals have private pools in Surfside?
There are 149 vacation rentals with private pools near Surfside. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Surfside are best for families?
If you are looking for a family-friendly vacation home in Surfside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Surfside:
4. How many Rentbyowner vacation rentals are available in Surfside?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1033 in the Surfside area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Surfside.
5. What is the cancellation policy for vacation rentals in Surfside, Nantucket?
Cancellation policies vary by property, so you should review the specific listing details or contact the property owner directly for the most accurate information related to cancellations and potential fees.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, security deposits, or service charges are detailed in each listing. It's advisable to read the full description or reach out to the owner for clarification before confirming your reservation.
7. How do I ensure my booking is secure and reliable when selecting a vacation rental in Nantucket?
Choosing listings with verified reviews, clear host information, and secure payment options helps ensure a trustworthy booking experience. Always communicate through the platform to protect your personal and payment details.
8. What amenities are typically available in vacation rentals in this destination?
Most properties offer essential amenities like Wi-Fi, kitchen facilities, and linens. However, specific features such as outdoor spaces or entertainment systems can vary, so check the individual listing to confirm what’s included.
9. How close are vacation rentals in this area to local attractions and beaches?
Many rentals are conveniently located near popular beaches and attractions, but proximity varies by property. Review the location details on each listing or contact the owner for precise distance information.
Surfside Top Rated Vacation Rentals
House
10.0(74 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $1,825/Night
7 Nights - AU $12,779
House
10.0(64 Reviews)
4 Bedrooms
3 Baths
8 Guests
2200 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $2,484/Night
7 Nights - AU $17,389
House
10.0(58 Reviews)
4 Bedrooms
5 Baths
12 Guests
4000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
AU $2,869/Night
7 Nights - AU $20,084
House
10.0(47 Reviews)
5 Bedrooms
4 Baths
11 Guests
3000 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $1,760/Night
7 Nights - AU $12,318
House
10.0(43 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
AU $3,339/Night
7 Nights - AU $23,372
House
10.0(42 Reviews)
4 Bedrooms
5 Baths
22 Guests
4400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
AU $2,242/Night
7 Nights - AU $15,694
House
10.0(40 Reviews)
5 Bedrooms
5 Baths
16 Guests
2542 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
AU $1,806/Night
7 Nights - AU $12,644
