Wine Country Villas - Vacation Rentals in Surfside

Beautiful and Spacious Ocean Front Spanish Villa Mansion From US $1,106
         

Seaview Beach House From US $712
         

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7.0 (2 Reviews)
Villa
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  • Pet Friendly

Luxury Places to Stay in Surfside

Over 1438+ Luxury Places to Stay in or Near Surfside
Bliss Street Beach House From US $3,028
         

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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)
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Family Tides Home for the Holidays From US $1,556
         

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New
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Top-Rated Vacation Rentals with a Pool in Surfside

Over 258+ Top-Rated Vacation Rentals with a Pool in or Near Surfside
Renting September 2025 to June 1, 2026 From US $130
         

10.0 (15 Reviews)
Condo
  • Air Conditioner
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  • Pet Friendly
Ocean Park Meadows Unit #4, Beautiful Condo From US $236
         

10.0 (13 Reviews)
Condo
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  • Pool
Oceanfront, 2 Bedroom Condo, 1 Mile From The Pier From US $324
         

Pet-Friendly Vacation Rentals in Surfside

Over 342+ 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
Cozy 1 Bedroom Cabin From US $301
         

8.0 (2 Reviews)
Cottage
  • Air Conditioner
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  • Pet Friendly
Beach House ∆ Prime Location ∆ Steps to the Ocean From US $485
         

10.0 (55 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Surfside on PetFriendly.io

Large Vacation Homes & Villas in Surfside

Over 235+ Large Vacation Homes & Villas in or Near Surfside
Spacious Family Suite Steps to the Beach (444) From US $886
         

10.0 (2 Reviews)
Apartment
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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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Blue Doors By The Sea by Bayley Vacation Rentals From US $885
         

Wheelchair Accessible Vacation Homes in Surfside

Over 109+ Wheelchair Accessible Vacation Homes in or Near Surfside
Waves Oceanfront Resort From US $930
         

7.5 (457 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
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Condo Room 207 Ocean view next to the pier From US $304
         

Adorable 1 bedroom cabin only 50 ft from beach#1 From US $197
         

10.0 (3 Reviews)
Cottage
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Cheerful 1 bedroom cottage only 50ft from beach From US $197
         

10.0 (2 Reviews)
Cottage
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Seawatch Oceanfront Unit 602 From US $460
         

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

Surfside Varoom and Airbnb Places to Stay Under $200

Over 199+ 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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Old Orchard Beach Inn From US $95
         

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

9.8 (42 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Surfside

Over 875+ Instantly Bookable Vacation Homes in or Near Surfside
Pine Point Beach - Private, quaint, charming space From US $322
         

10.0 (17 Reviews)
Apartment
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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
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  • TV

About Surfside Vacation Rentals

With more than 2 Surfside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Winecountryvillas 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 Winecountryvillas 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 2998.78 ft² on average, with prices averaging $909 a night.

Winecountryvillas 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
Villas 2

Use these Quick Filters to Find a Vacation Rental in Surfside

Pro Tip: Winecountryvillas makes it easy to compare the best listings on Winecountryvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winecountryvillas 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