Winter Park Villas - Vacation Rentals in Osprey Point Golf Course
Cottage
9.8
(
132 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1300 ft²
-
Oceanfront -
Parking -
Pool -
Ocean View
US $552
/Night
7 Nights - $3,864
Villa
8.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
828.82 ft²
-
Parking
-
Balcony/Terrace -
Air Conditioner -
Internet
US $100
/Night
7 Nights - $700
House
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1300 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $427
/Night
7 Nights - $2,991
House
10.0
(
76 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
2100 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,152
/Night
7 Nights - $8,066
House
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
2314.24 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $194
/Night
7 Nights - $1,358
Condo
9.4
(
3 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1251 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $297
/Night
7 Nights - $2,077
House
9.8
(
78 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
2700 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $1,007
/Night
7 Nights - $7,048
House
3 Bedrooms
5 Bathrooms
8 Guests
3304.52 ft²
-
Private Beach -
Parking
-
Ocean View
-
Balcony/Terrace
US $399
/Night
7 Nights - $2,793
House
9.6
(
106 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $670
/Night
7 Nights - $4,689
House
9.6
(
125 Reviews
)
6 Bedrooms
6 Bathrooms
14 Guests
4240 ft²
-
Private Pool -
Oceanfront
-
Parking
-
Pool
US $2,044
/Night
7 Nights - $14,307
Condo
9.6
(
63 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1356 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $741
/Night
7 Nights - $5,186
House
9.2
(
37 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2107 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $674
/Night
7 Nights - $4,715
House
9.6
(
125 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $510
/Night
7 Nights - $3,567
Cottage
10.0
(
154 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1380 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $502
/Night
7 Nights - $3,513
Condo
9.8
(
152 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
800 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $705
/Night
7 Nights - $4,936
Condo
9.8
(
120 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1157 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $891
/Night
7 Nights - $6,236
House
9.8
(
119 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
3186 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $621
/Night
7 Nights - $4,346
Condo
9.8
(
111 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1348 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $995
/Night
7 Nights - $6,964
Villa
9.8
(
101 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $836
/Night
7 Nights - $5,855
Villa
9.8
(
57 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1250 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $994
/Night
7 Nights - $6,957
House
9.6
(
125 Reviews
)
6 Bedrooms
5 Bathrooms
14 Guests
6352 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $3,299
/Night
7 Nights - $23,092
Condo
9.2
(
48 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1617 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $996
/Night
7 Nights - $6,970
House
8.6
(
50 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
3000 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $720
/Night
7 Nights - $5,039
House
10.0
(
36 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $413
/Night
7 Nights - $2,893
★ 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 Osprey Point Golf Course.
Weather in Osprey Point Golf Course
View the weather forecast for Osprey Point Golf Course before booking your Osprey Point Golf Course 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
Osprey Point Golf Course Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Osprey Point Golf Course?
There are a lot of options in Osprey Point Golf Course. If you plan on staying in the Osprey Point Golf Course area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Osprey Point Golf Course:
- Villa Overlooking Roy Barth Tennis Courts- 5 Minute Walk to Beach
- Sunroom with lagoon views to enjoy nature! Discounts for long, off-season stays!
- Tranquil villa just steps from the beach!
- Private 3 Bdrm Oceanwoods home short walk to the beach wifi deck and grill.
- 2 Min.Walk to Beach. Charming, spacious 3bd;3ba home. Hear the Ocean from Porch
- Oceanwoods 3bd/2bth w/Enlarged Screen Porch, WiFi, updated!
- Kiawah Island, 5 Bdrs, 4 Bath, 3054 sf, golf course view, walk/bike to beach
- Romantic Oceanfront Escape for Couples
- Private, Unique Home w/Large 8 Foot Deep Pool, Walk to Beach, Water View
- 10 Min Walk To Beach Dog Friendly Renovated Villa With Custom, High End Finishes & Lagoon Views
How many vacation rentals are available in Osprey Point Golf Course?
Currently, the total number of properties listed in 2026 is over 1411 in the Osprey Point Golf Course area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osprey Point Golf Course.
