Pirate Cove Cottages - Vacation Rentals in Surfside

Little Miss Cottages - 68 East Grand Luxury Condo From US $628
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • View
Little Miss Cottages From US $507
         

8.4 (83 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1 Bedroom Cabin From US $228
         

8.0 (2 Reviews)
Cottage
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  • Pet Friendly
Nautical View From US $408
         

10.0 (19 Reviews)
Cottage
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  • TV
Updated Cottage - Steps to Pine Point Beach! From US $223
         

10.0 (17 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Surfside

Over 1434+ Luxury Places to Stay in or Near Surfside
Bliss Street Beach House by Bayley Vacation Rental From US $3,028
         

Bliss Street Beach House From US $3,027
         

New
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5 BR 3 Bath Waterfront Beach Home From US $2,180
         

9.6 (28 Reviews)
House
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Family Tides by Bayley Vacation Rentals From US $1,556
         

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New
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Top-Rated Vacation Rentals with a Pool in Surfside

Over 256+ Top-Rated Vacation Rentals with a Pool in or Near Surfside
Renting September 2025 to June 1, 2026 From US $124
         

10.0 (15 Reviews)
Condo
  • Air Conditioner
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  • Pet Friendly
Ocean Park Meadows Unit #4, Beautiful Condo From US $251
         

10.0 (13 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Oceanfront, 2 Bedroom Condo, 1 Mile From The Pier From US $325
         

Pet-Friendly Vacation Rentals in Surfside

Over 348+ Pet-Friendly Vacation Rentals in or Near Surfside
Grand Beach Inn From US $162
         

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7.2 (1003 Reviews)
Hotel
  • Air Conditioner
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  • Pet Friendly
Beach House ∆ Prime Location ∆ Steps to the Ocean From US $383
         

10.0 (56 Reviews)
House
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  • Pet Friendly
Quiet Ocean Breeze Cottage From US $394
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Surfside on PetFriendly.io

Large Vacation Homes & Villas in Surfside

Over 238+ Large Vacation Homes & Villas in or Near Surfside
Spacious Family Suite Steps to the Beach (444) From US $886
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • View
  • Security/Safety
Walking Distance To Beach And Downtown! From US $894
         

4 Bdr Vacation Rental - Walk to Beach From US $681
         

9.2 (17 Reviews)
House
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  • Parking
  • TV
Blue Doors By The Sea by Bayley Vacation Rentals From US $882
         

Wheelchair Accessible Vacation Homes in Surfside

Over 108+ Wheelchair Accessible Vacation Homes in or Near Surfside
Waves Oceanfront Resort From US $930
         

7.7 (444 Reviews)
Resort
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  • Pool
Black Point Inn From US $577
         

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9.2 (62 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Condo Room 207 Ocean view next to the pier From US $307
         

Adorable 1 bedroom cabin only 50 ft from beach#1 From US $206
         

10.0 (3 Reviews)
Cottage
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  • Pet Friendly
Cheerful 1 bedroom cottage only 50ft from beach From US $227
         

10.0 (2 Reviews)
Cottage
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  • Parking
  • Pet Friendly
Seawatch Oceanfront Unit 602 From US $460
         

10.0 (1 Review)
Condo
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  • Pool
Grand Victorian ocean view, Unit 409 From US $456
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool

Surfside Varoom and Airbnb Places to Stay Under $200

Over 204+ Surfside Varoom and Airbnb Places to Stay Under $200
Sea Shell From US $146
         

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10.0 (4 Reviews)
House
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  • View
Old Orchard Beach Inn From US $119
         

8.2 (1000 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Cozy 1 BR Condo Steps From The Beach From US $162
         

9.8 (42 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beachy retreat! From US $196
         

9.8 (6 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Surfside

Over 872+ Instantly Bookable Vacation Homes in or Near Surfside
Pine Point Beach - Private, quaint, charming space From US $322
         

10.0 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Perfect Location & Best Prices! 5th house from the Beach From US $222
         

3 Bdr Vacation Rental - Walk To The Beach From US $409
         

9.6 (22 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Atlantic Ocean Suites - Sand Castle Suite 7 From US $516
         

About Surfside Vacation Rentals

With more than 148 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 904.71 ft² on average, with prices averaging $382 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 132
Vacation Homes 13
Hotels with Suites 2
Holiday Apartments 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 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F