Guide For Orlando - Vacation Rentals in Surfside

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant! From US $1,396
         

52 Union From US $2,150
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • View
29 India House From US $383
         

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10.0 (28 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Charming cottage, close to lower Main Street. From US $894
         

10.0 (130 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
BEAUTIFUL BUNGALOW on ORANGE ST, WALK TO TOWN! From US $1,098
         

Recently Remodeled - Walk to Everything! From US $1,229
         

10.0 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Surfside

Over 1048+ Luxury Places to Stay in or Near Surfside
LUXURIOUS NEW Harbor View Home From US $8,280
         

New
House
  • Air Conditioner
  • Parking
  • 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 $5,752
         

New
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Surfside

Over 274+ Top-Rated Vacation Rentals with a Pool in or Near Surfside
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything! From US $1,347
         

Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything! From US $1,247
         

LUXURIOUS NEW Harbor View Home with Hinckley Yacht! From US $3,435
         

10.0 (71 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Surfside

Over 220+ 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
New In Town Time & Tide Cottage From US $1,947
         

9.6 (40 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Surfside on PetFriendly.io

Large Vacation Homes & Villas in Surfside

Over 361+ Large Vacation Homes & Villas in or Near Surfside
Union Street Inn From US $879
         

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9.7 (53 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Nantucket Main Street Charm From US $2,308
         

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 $950
         

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9.6 (342 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 $538
         

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9.4 (195 Reviews)
Hotel
  • Air Conditioner
  • TV
  • View

Surfside Vacation Rentals and Airbnb Places to Stay Under $200

Over 7+ 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
  • Parking
  • TV
Brass Lantern Inn From US $175
         

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9.3 (29 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Languedoc Inn & 3 Hussey St Guest House From US $145
         

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
Convenient Mid Island House Nantucket-5 Bedrooms From US $117
         

New
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities

Instantly Bookable Vacation Homes in Surfside

Over 252+ Instantly Bookable Vacation Homes in or Near Surfside
SUNNY second floor 2BD, 2BT From US $911
         

9.6 (15 Reviews)
Apartment
  • Air Conditioner
  • TV
  • View
Private Modern Bedroom In a Central Location From US $497
         

9.6 (23 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
BRIGHT and STYLISH 2BD,1BT with deck and BBQ From US $1,126
         

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 1057 Surfside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Guidefororlando 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 Guidefororlando 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 876.98 ft² on average, with prices averaging US $1,761 a night.

Guidefororlando 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
Vacation Homes 840
Cottages 74
Holiday Apartments 61
Hotels 41
B&B 17
Cabin Rentals 1
Resorts 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Surfside

Pro Tip: Guidefororlando makes it easy to compare the best listings on Guidefororlando homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Guidefororlando 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 1057 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.