Winter Park Villas - Vacation Rentals in Calusa Beach
House
10.0
(
15 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
2500 ft²
-
Private Pool -
Oceanfront -
Parking -
Pool
US $595
/Night
7 Nights - $4,163
House
8.9
(
20 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
290.63 ft²
-
Parking
-
Pool
-
Ocean View -
Balcony/Terrace
US $238
/Night
7 Nights - $1,666
House
8.8
(
180 Reviews
)
1 Bedroom
1 Bathroom
-
Pool
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $343
/Night
7 Nights - $2,402
House
10.0
(
34 Reviews
)
3 Bedrooms
4 Bathrooms
8 Guests
2000 ft²
-
Private Pool
-
Pool
-
Balcony/Terrace
-
View
US $1,066
/Night
7 Nights - $7,460
Apartment
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Air Conditioner
US $7,000
/Night
7 Nights - $49,000
Cottage
8.6
(
374 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $250
/Night
7 Nights - $1,752
House
10.0
(
10 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1200 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $510
/Night
7 Nights - $3,567
Bed & Breakfast
9.8
(
5 Reviews
)
4 Bedrooms
4 Bathrooms
6 Guests
145.31 ft²
-
Private Beach -
Oceanfront
-
Hot Tub -
Breakfast
US $495
/Night
7 Nights - $3,465
House
10.0
(
9 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2882 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $406
/Night
7 Nights - $2,842
House
10.0
(
8 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $648
/Night
7 Nights - $4,539
House
10.0
(
8 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1500 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $592
/Night
7 Nights - $4,145
House
10.0
(
7 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $270
/Night
7 Nights - $1,892
House
10.0
(
7 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
889 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $191
/Night
7 Nights - $1,336
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
960 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $283
/Night
7 Nights - $1,981
House
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1700 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $243
/Night
7 Nights - $1,702
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $228
/Night
7 Nights - $1,594
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $596
/Night
7 Nights - $4,175
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $557
/Night
7 Nights - $3,899
House
10.0
(
3 Reviews
)
2 Bedrooms
3 Bathrooms
4 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $323
/Night
7 Nights - $2,264
House
10.0
(
2 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
2592 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,277
/Night
7 Nights - $8,941
House
10.0
(
2 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
2467 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Balcony/Terrace
US $472
/Night
7 Nights - $3,307
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
8 Guests
1600 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $448
/Night
7 Nights - $3,133
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $385
/Night
7 Nights - $2,693
US $249
/Night
7 Nights - $1,746
โ 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 Calusa Beach.
Weather in Calusa Beach
View the weather forecast for Calusa Beach before booking your Calusa Beach Vacation Rentals to confirm your best time to go.
December - February
High 81ยฐF Low 67ยฐF
March - May
High 87ยฐF Low 70ยฐF
June - August
High 91ยฐF Low 80ยฐF
September - November
High 90ยฐF Low 73ยฐF
Calusa Beach Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Calusa Beach?
There are a lot of options in Calusa Beach. If you plan on staying in the Calusa 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 Calusa Beach:
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
- Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
- BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL BIG PINE KEY FL
- Gorgeous Beachfront Home with a pool. Water views from every direction.
- Excellent boating location-65 ft frontage on deep canal
- Charming 2-bedroom 2- bath home located in the middle of The Key Deer Refuge.
- Pool house with open water and sunset in the Florida Keys
- Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage!
How many vacation rentals are available in Calusa Beach?
Currently, the total number of properties listed in 2026 is over 235 in the Calusa Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Calusa Beach.
