Surfside Holiday Rentals
- Nantucket
- ·
- Nantucket Town
- 0.28 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Nantucket
- ·
- Nantucket Town
- 0.50 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.19 mi to center
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
- Nantucket
- ·
- Nantucket Town
- 0.62 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Nantucket
- ·
- Nantucket Town
- 0.35 mi to center
- Oceanfront
- Breakfast
- Parking
- Ocean View
- Nantucket
- ·
- Nantucket Town
- 0.28 mi to center
- Child Friendly
- Nantucket
- ·
- Nantucket Town
- 1.38 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Massachusetts
- ·
- Nantucket
- 2.24 mi to center
- Parking
- Pool
- Balcony/Terrace
- Kitchen
- Nantucket
- ·
- Nantucket Town
- 0.48 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
Luxury Holiday Rentals in Surfside
- Nantucket
- ·
- Nantucket Town
- 0.56 mi to center
- Hot Tub
- Parking
- Pool
- Ocean View
- Massachusetts
- ·
- Nantucket
- 3.20 mi to center
- Air Conditioner
- Internet
- Child Friendly
- Laundry
- Pool
- Balcony/Terrace
- Child Friendly
- Security/Safety
- Nantucket
- ·
- Nantucket Town
- 0.37 mi to center
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
- Massachusetts
- ·
- Nantucket
- 1.96 mi to center
- Air Conditioner
- Internet
- Child Friendly
- Laundry
- Nantucket
- ·
- Nantucket Town
- 0.42 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Massachusetts
- ·
- Nantucket
- 1.78 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Massachusetts
- ·
- Nantucket
- 2.98 mi to center
- Private Pool
- Hot Tub
- Parking
- Pool
- Nantucket
- ·
- Nantucket Town
- 0.31 mi to center
- Private Pool
- Parking
- Pool
- Ocean View
Top-Rated Holiday Rentals with a Pool in Surfside
- Nantucket
- ·
- Nantucket Town
- 0.52 mi to center
- Oceanfront
- Parking
- Pool
- Spa
- Nantucket
- ·
- Nantucket Town
- 0.03 mi to center
- Oceanfront
- Parking
- Pool
- Spa
- Nantucket
- ·
- Nantucket Town
- 0.47 mi to center
- Oceanfront
- Parking
- Pool
- Spa
- Nantucket
- ·
- West of Town
- 0.33 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Massachusetts
- ·
- Nantucket
- 1.40 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Nantucket
- ·
- Nantucket Town
- 0.44 mi to center
- Oceanfront
- Hot Tub
- Parking
- Pool
- Nantucket
- ·
- Nantucket Town
- 0.32 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Massachusetts
- ·
- Nantucket
- 1.41 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Nantucket
- ·
- Brant Point
- 0.24 mi to center
- Breakfast
- Pool
- Ocean View
- View
Pet-Friendly Holiday Rentals in Surfside
- Nantucket
- ·
- Nantucket Town
- 0.44 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Nantucket
- ·
- Nantucket Town
- 0.19 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.43 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- West of Town
- 0.40 mi to center
- Parking
- Balcony/Terrace
- View
- Air Conditioner
- Nantucket
- ·
- Nantucket Town
- 0.58 mi to center
- Parking
- Air Conditioner
- Internet
- Pet Friendly
- Nantucket
- ·
- Nantucket Town
- 0.30 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 1.03 mi to center
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
- Nantucket
- ·
- Nantucket Town
- 0.10 mi to center
- Breakfast
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.19 mi to center
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
Large Holiday Rentals and Private Villas in Surfside
- Nantucket
- ·
- Nantucket Town
- 0.39 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.31 mi to center
- Breakfast
- Parking
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.27 mi to center
- Oceanfront
- Parking
- Ocean View
- View
- Nantucket
- ·
- Nantucket Town
- 0.40 mi to center
- Oceanfront
- Breakfast
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.34 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Massachusetts
- ·
- Nantucket
- 2.49 mi to center
- Private Pool
- Parking
- Pool
- Ocean View
- Nantucket
- ·
- Nantucket Town
- 0.31 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.42 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.03 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
Wheelchair Accessible Holiday Homes in Surfside
- Nantucket
- ·
- Nantucket Town
- 0.31 mi to center
- Oceanfront
- Hot Tub
- Parking
- Pool
- Nantucket
- ·
- Nantucket Town
- 0.59 mi to center
- Breakfast
- Parking
- Spa
- Balcony/Terrace
- Nantucket
- ·
- Brant Point
- 0.31 mi to center
- Breakfast
- Parking
- Pool
- Spa
- Nantucket
- ·
- Nantucket Town
- 0.34 mi to center
- Private Pool
- Hot Tub
- Parking
- Pool
- Nantucket
- ·
- Nantucket Town
- 0.36 mi to center
- Balcony/Terrace
- View
- Air Conditioner
- Internet
- Nantucket
- ·
- Nantucket Town
- 0.45 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Nantucket
- ·
- West of Town
- 0.42 mi to center
- Private Pool
- Oceanfront
- Parking
- Pool
- Nantucket
- ·
- Nantucket Town
- 0.31 mi to center
- Private Pool
- Breakfast
- Parking
- Pool
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
Surfside Private Villas and Holiday Homes Under $200
- Nantucket
- ·
- Nantucket Town
- 1.04 mi to center
- Internet
- Laundry
- Bedding/Linens
- Wellness Facilities
- Nantucket
- ·
- Brant Point
- 0.28 mi to center
- Parking
- Balcony/Terrace
- View
- Air Conditioner
- Nantucket
- ·
- Nantucket Town
- 0.30 mi to center
- Ocean View
- Balcony/Terrace
- View
- Kitchen
- Nantucket
- ·
- West of Town
- 0.70 mi to center
- Internet
- Child Friendly
- Laundry
- Bedding/Linens
- Massachusetts
- ·
- Nantucket
- 2.19 mi to center
- Child Friendly
Instantly Bookable Holiday Homes in Surfside
- Nantucket
- ·
- Nantucket Town
- 0.35 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.99 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.34 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.07 mi to center
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.59 mi to center
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- Nantucket Town
- 0.42 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.46 mi to center
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
- Nantucket
- ·
- West of Town
- 0.36 mi to center
- Parking
- Ocean View
- Balcony/Terrace
- View
- Nantucket
- ·
- Nantucket Town
- 0.37 mi to center
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
Book a Last Minute Place to Stay in Surfside
About Casai's Private Villas and Holiday Rentals in Surfside
Discover more than 1033 vacation rentals available in Surfside. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Surfside.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Surfside, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Surfside. On average, places to stay near Surfside offer 860.37 ft², with nightly prices averaging R28,784.
With Casai, finding and comparing holiday rentals in Surfside is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Surfside
| Type | Count |
|---|---|
| Vacation Homes | 824 |
| Cottages | 66 |
| Holiday Apartments | 61 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Surfside
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Surfside.
Weather in Surfside, MA
View the weather forecast for Surfside before booking your Surfside Vacation Rentals to confirm your best time to go.
Top Attractions Around Surfside, MA
Casai offers a large selection of top attractions around Surfside . Research things to do on your vacation before you visit Surfside.
Frequently Asked Questions About Surfside?
What are the top holiday rentals in Surfside?
With numerous options available in Surfside, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
How many holiday rentals have private pools in Surfside?
Discover a selection of holiday rentals with private pools near Surfside with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Private Poolside Nantucket Retreat Near the Beach and Conservation
- Nantucket Inn
- 2 bedroom, 2.5 bathroom
- Pool, Outdoor Kitchen, Bocce court, 2 game rooms about 1.5mi from Surfside Beach
Which holiday homes in Surfside are best for families?
If you're searching for a family-friendly holiday home in Surfside, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Surfside:
How many Casai.co.za holiday rentals are available in Surfside?
As of 2026, Casai boasts over 1033 properties listed in the Surfside area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Surfside.



































































