Pirate Cove Cottages - Vacation Rentals in Surfside

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant! From US $1,713
         

Sail Away Cottage From US $1,326
         

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8.5 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Harborview Nantucket From US $670
         

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9.8 (16 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Charming cottage, close to lower Main Street. From US $972
         

10.0 (128 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Surfside

Over 1049+ Luxury Places to Stay in or Near Surfside
LUXURIOUS NEW Harbor View Home From US $7,446
         

New
House
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  • Pet Friendly
Stunning Surfside 6 bedroom Estate With Pool and Cabana From US $6,554
         

9.8 (7 Reviews)
House
  • Pool
  • Balcony/Terrace
  • Security/Safety
5 bedroom, 7 bathroom From US $5,669
         

New
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Surfside

Over 272+ Top-Rated Vacation Rentals with a Pool in or Near Surfside
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything! From US $1,634
         

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches From US $949
         

Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything! From US $1,908
         

LUXURIOUS NEW Harbor View Home with Hinckley Yacht! From US $1,927
         

10.0 (68 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Surfside

Over 223+ Pet-Friendly Vacation Rentals in or Near Surfside
The Bungalow From US $1,930
         

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9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Renovated Cottage off Main Street- Great Location From US $586
         

10.0 (166 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautifully Renovated Main Street Cottage- Great Location From US $638
         

10.0 (126 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Surfside on PetFriendly.io

Large Vacation Homes & Villas in Surfside

Over 367+ Large Vacation Homes & Villas in or Near Surfside
Recently Remodeled - Walk to Everything! From US $1,196
         

10.0 (76 Reviews)
Apartment
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  • TV
52 Union From US $2,150
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • View
Nantucket Main Street Charm From US $2,383
         

10.0 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Surfside

Over 14+ Wheelchair Accessible Vacation Homes in or Near Surfside
Nantucket Periwinkle From US $129
         

8.4 (103 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
White Elephant Hotel From US $783
         

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9.6 (341 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
White Elephant Hotel From US $1,628
         

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9.2 (96 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Greydon House From US $320
         

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9.4 (194 Reviews)
Hotel
  • Air Conditioner
  • TV
  • View

Surfside Vacation Rentals and Airbnb Places to Stay Under $200

Over 10+ Surfside Vacation Rentals and Airbnb Places to Stay Under $200
Private Modern Bedroom In a Central Location From US $180
         

9.2 (30 Reviews)
Apartment
  • Air Conditioner
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  • TV
Brass Lantern Inn From US $175
         

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9.3 (29 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Periwinkle Inn From US $175
         

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8.8 (182 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • View
4-Bedroom House, Mid-Island Nantucket From US $182
         

10.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Cliff Lodge From US $138
         

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8.5 (226 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Languedoc Inn & 3 Hussey St Guest House From US $145
         

Centerboard From US $135
         

9.8 (105 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Surfside

Over 259+ Instantly Bookable Vacation Homes in or Near Surfside
BEAUTIFUL BUNGALOW on ORANGE ST, WALK TO TOWN! From US $1,075
         

Private Modern Bedroom In a Central Location From US $497
         

9.6 (23 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
SUNNY second floor 2BD, 2BT From US $916
         

9.6 (15 Reviews)
Apartment
  • Air Conditioner
  • TV
  • View
BRIGHT and STYLISH 2BD,1BT with deck and BBQ From US $1,128
         

9.8 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Designer House on Lily Street in Town! A/C! From US $1,676
         

About Surfside Vacation Rentals

With more than 77 Surfside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Piratecovecottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Surfside.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Surfside, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Surfside. Places to stay near Surfside are 641.42 ft² on average, with prices averaging US $1,119 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Surfside with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Surfside

Type Count
Cottages 75
Hotels 1
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Surfside

Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Surfside.

Weather in Surfside

View the weather forecast for Surfside before booking your Surfside Vacation Rentals to confirm your best time to go.

December - February
High 45°F       Low 24°F
March - May
High 66°F       Low 27°F
June - August
High 81°F       Low 59°F
September - November
High 77°F       Low 35°F

Surfside Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Surfside?
How many vacation rentals are available in Surfside?

Currently, the total number of properties listed in 2026 is over 77 in the Surfside area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Surfside.