Winter Park Villas - Vacation Rentals in South Beach
House
10.0
(
64 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
896 ft²
-
Parking -
Pool -
Balcony/Terrace -
Kitchen
US $478
/Night
7 Nights - $3,349
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1388.54 ft²
-
Balcony/Terrace
-
View -
Air Conditioner -
Internet
US $873
/Night
7 Nights - $6,111
Bed & Breakfast
9.8
(
283 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $363
/Night
7 Nights - $2,539
House
9.8
(
60 Reviews
)
6 Bedrooms
2 Bathrooms
10 Guests
2000 ft²
-
Parking
-
Ocean View -
Balcony/Terrace
-
View
US $766
/Night
7 Nights - $5,360
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
8 Guests
1905.21 ft²
-
Parking
-
Internet
-
Child Friendly -
Sports/Activities
US $514
/Night
7 Nights - $3,600
House
9.4
(
219 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $248
/Night
7 Nights - $1,734
House
10.0
(
51 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $918
/Night
7 Nights - $6,429
Bed & Breakfast
8.9
(
102 Reviews
)
14 Bedrooms
8 Bathrooms
16 Guests
157.42 ft²
-
Oceanfront -
Breakfast
-
Ocean View
-
Balcony/Terrace
US $493
/Night
7 Nights - $3,449
House
10.0
(
26 Reviews
)
6 Bedrooms
5 Bathrooms
12 Guests
4000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $3,299
/Night
7 Nights - $23,092
House
9.8
(
59 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1225 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $925
/Night
7 Nights - $6,474
House
9.8
(
17 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1600 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $564
/Night
7 Nights - $3,948
House
10.0
(
51 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2000 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $906
/Night
7 Nights - $6,341
House
10.0
(
33 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $928
/Night
7 Nights - $6,495
House
10.0
(
17 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
2500 ft²
-
Private Pool -
Oceanfront
-
Hot Tub -
Parking
US $1,478
/Night
7 Nights - $10,345
House
10.0
(
14 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $1,661
/Night
7 Nights - $11,629
House
10.0
(
12 Reviews
)
3 Bedrooms
4 Bathrooms
11 Guests
4000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,143
/Night
7 Nights - $7,998
House
10.0
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1950 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,053
/Night
7 Nights - $7,368
House
10.0
(
10 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $1,240
/Night
7 Nights - $8,683
Cottage
10.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $617
/Night
7 Nights - $4,316
House
10.0
(
8 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,146
/Night
7 Nights - $8,025
House
10.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2648 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $793
/Night
7 Nights - $5,548
House
10.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1700 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $538
/Night
7 Nights - $3,764
House
10.0
(
6 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1344 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $626
/Night
7 Nights - $4,379
Condo
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Ocean View
-
Balcony/Terrace
-
View
-
Kitchen
US $262
/Night
7 Nights - $1,832
★ Pro Tip: Winterparkvillas makes it easy to compare the best listings on Winterparkvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winterparkvillas 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 South Beach.
Weather in South Beach
View the weather forecast for South Beach before booking your South Beach 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
South Beach Vacation Rental Frequently Asked Questions
What are the top vacation rentals in South Beach?
There are a lot of options in South Beach. If you plan on staying in the South Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Beach:
- Luxury Katama 5BR - Pool, Hot Tub, Bocce & Firepit Steps from South Beach
- Edgartown - Vacation Home In A Great Location!
- Captain Morse House Luxury - In Town, Walk to Waterfront, Beach, Pets, 5 stars
- Edgartown Family Getaway! Now Booking 2027!
- Light-Filled Romantic Cottage Close to Village, Beach, Bike Path, Nature Trails
- Perfect Family Home, walk or bike to town
- Edgartown close to beach and town 6BD with Pool and Hot Tub
- 5 minute walk to downtown Edgartown, very close ride to State Beach/South Beach.
- Walk to Village Bike to beach - AC, 4 BdRms 3 Full Baths, Sleeps 8: Immaculate!
- Walk to Edgartown Wharf - Upgraded Vineyard Home with AC and Outdoor Shower
How many vacation rentals are available in South Beach?
Currently, the total number of properties listed in 2026 is over 388 in the South Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Beach.
