Estia Villas - Vacation Rentals in Winona
Apartment
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
15 Guests
-
Balcony/Terrace -
Parking -
Air Conditioner -
Internet
US $540
/Night
7 Nights - $3,780
Hotel
8.0
(
501 Reviews
)
1 Bathroom
-
Pool -
Balcony/Terrace
-
Breakfast -
Kitchen
US $108
/Night
7 Nights - $755
House
10.0
(
43 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
-
Fireplace/Heating -
Pet Friendly -
Kitchen
-
Air Conditioner
US $235
/Night
7 Nights - $1,648
House
10.0
(
34 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1100 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $167
/Night
7 Nights - $1,171
Cabin
10.0
(
15 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $241
/Night
7 Nights - $1,685
Apartment
10.0
(
14 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
400 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $103
/Night
7 Nights - $722
Cabin
10.0
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
3000 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $233
/Night
7 Nights - $1,630
House
10.0
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1600 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $181
/Night
7 Nights - $1,267
See More Winona Vacation Rentals
Luxury Places to Stay in Winona
Over 127+
Luxury Places to Stay in or Near Winona
US $3,745
/Night
7 Nights - $26,215
US $3,318
/Night
7 Nights - $23,225
House
9.4
(
3 Reviews
)
4 Bedrooms
3 Bathrooms
14 Guests
-
Pet Friendly
-
Child Friendly -
Security/Safety
US $608
/Night
7 Nights - $4,258
3 Bedrooms
2 Bathrooms
8 Guests
1905.21 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View -
Pet Friendly
US $440
/Night
7 Nights - $3,080
House
8.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Child Friendly
-
Laundry
US $436
/Night
7 Nights - $3,052
House
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Internet
-
Child Friendly
US $431
/Night
7 Nights - $3,019
House
3 Bedrooms
2 Bathrooms
8 Guests
1900 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $405
/Night
7 Nights - $2,836
New
House
3 Bedrooms
4 Bathrooms
8 Guests
4200 ft²
-
Fireplace/Heating
-
Air Conditioner
-
Internet
-
Child Friendly
US $386
/Night
7 Nights - $2,700
See More Winona Luxury Vacation Rentals
Find More Winona Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Winona
Over 25+
Top-Rated Vacation Rentals with a Pool in or Near Winona
Cabin
9.6
(
148 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2500 ft²
-
Private Pool -
Hot Tub -
Spa -
Fireplace/Heating
US $277
/Night
7 Nights - $1,940
8.5
(
216 Reviews
)
1 Bathroom
355.21 ft²
-
Oceanfront -
Fireplace/Heating
-
Pool
-
Ocean View
US $136
/Night
7 Nights - $949
8.5
(
153 Reviews
)
1 Bathroom
305.7 ft²
-
Oceanfront
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $207
/Night
7 Nights - $1,449
US $93
/Night
7 Nights - $651
Hotel
8.0
(
1 Review
)
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Parking
US $73
/Night
7 Nights - $512
Hotel
7.7
(
142 Reviews
)
8 Bathrooms
-
Fireplace/Heating
-
Pool
-
Breakfast
-
Pet Friendly
US $125
/Night
7 Nights - $875
7.5
(
106 Reviews
)
1 Bathroom
322.92 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Parking
US $146
/Night
7 Nights - $1,019
7.4
(
115 Reviews
)
1 Bathroom
-
Pool
-
Parking
-
Air Conditioner
-
Internet
US $136
/Night
7 Nights - $952
See More Winona Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Winona
Over 35+
Pet-Friendly Vacation Rentals in or Near Winona
9.5
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1819.1 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Parking
US $300
/Night
7 Nights - $2,102
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Pet Friendly
-
Air Conditioner
-
Child Friendly
-
Laundry
US $135
/Night
7 Nights - $945
Cabin
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
240 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
US $318
/Night
7 Nights - $2,225
Cabin
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $201
/Night
7 Nights - $1,410
Cabin
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $108
/Night
7 Nights - $756
Cabin
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $152
/Night
7 Nights - $1,064
Cabin
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Pet Friendly
-
Child Friendly
-
Laundry
-
Security/Safety
US $108
/Night
7 Nights - $756
Cabin
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $108
/Night
7 Nights - $756
See More Pet-Friendly Vacation Rentals in Winona on PetFriendly.io
Large Vacation Homes & Villas in Winona
Over 4+
Large Vacation Homes & Villas in or Near Winona
Cabin
9.4
(
52 Reviews
)
3 Bedrooms
2 Bathrooms
100 Guests
1815 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View
-
Kitchen
US $280
/Night
7 Nights - $1,958
House
8.4
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1250 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
US $229
/Night
7 Nights - $1,603
House
10.0
(
4 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Pet Friendly
US $589
/Night
7 Nights - $4,120
House
4 Bedrooms
3 Bathrooms
10 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Air Conditioner
-
Internet
US $115
/Night
7 Nights - $802
See More Family Vacation Rentals in Winona on FVR
Wheelchair Accessible Vacation Homes in Winona
Over 7+
Wheelchair Accessible Vacation Homes in or Near Winona
7.7
(
316 Reviews
)
10 Bathrooms
356.29 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
-
Parking
US $132
/Night
7 Nights - $924
Hotel
8.6
(
596 Reviews
)
1 Bathroom
-
Pool
-
Breakfast
-
Kitchen
-
Parking
US $163
/Night
7 Nights - $1,140
7.7
(
126 Reviews
)
5 Bathrooms
204.51 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $70
/Night
7 Nights - $490
US $161
/Night
7 Nights - $1,124
Hotel
8.0
(
825 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Breakfast
-
Kitchen
-
Parking
US $166
/Night
7 Nights - $1,163
Hotel
4.8
(
163 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Breakfast
US $499
/Night
7 Nights - $3,493
Hotel
4.6
(
103 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Balcony/Terrace
-
Breakfast
-
Kitchen
US $78
/Night
7 Nights - $546
Winona Vacation Rentals and Airbnb Places to Stay Under $200
Over 67+
Winona Vacation Rentals and Airbnb Places to Stay Under $200
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
6 Guests
1302.43 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Parking
-
Air Conditioner
US $140
/Night
7 Nights - $980
Hotel
6.8
(
148 Reviews
)
1 Bathroom
-
Kitchen
-
Air Conditioner
-
Child Friendly
-
Laundry
US $66
/Night
7 Nights - $462
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1600 ft²
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Air Conditioner
US $177
/Night
7 Nights - $1,242
Apartment
10.0
(
5 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
400 ft²
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $116
/Night
7 Nights - $812
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Kitchen
-
Air Conditioner
-
Child Friendly
US $186
/Night
7 Nights - $1,305
Cabin
9.8
(
48 Reviews
)
1 Bedroom
1 Bathroom
9 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $146
/Night
7 Nights - $1,024
Apartment
9.8
(
10 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1900 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $191
/Night
7 Nights - $1,338
Cabin
9.6
(
17 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $183
/Night
7 Nights - $1,283
See More Winona Vacation Rental Deals
Instantly Bookable Vacation Homes in Winona
Over 35+
Instantly Bookable Vacation Homes in or Near Winona
House
10.0
(
3 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $325
/Night
7 Nights - $2,276
Cabin
10.0
(
1 Review
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Child Friendly
-
Laundry
US $311
/Night
7 Nights - $2,175
Cottage
9.8
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Air Conditioner
US $367
/Night
7 Nights - $2,569
Apartment
9.8
(
9 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
2400 ft²
-
Fireplace/Heating
-
Breakfast
-
Kitchen
-
Parking
US $241
/Night
7 Nights - $1,685
Cabin
9.4
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
-
Parking
US $108
/Night
7 Nights - $756
House
9.2
(
9 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $212
/Night
7 Nights - $1,483
Cabin
8.4
(
5 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $182
/Night
7 Nights - $1,275
Cabin
2 Bedrooms
1 Bathroom
4 Guests
-
Hot Tub
-
Fireplace/Heating
-
Balcony/Terrace
-
Pet Friendly
US $258
/Night
7 Nights - $1,806
See More Winona Short-Term Vacation Rentals
About Winona Vacation Rentals
With more than 136 Winona vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas 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 Winona.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Winona, 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 Winona. Places to stay near Winona are 398.26 ft² on average, with prices averaging US $257 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Winona 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 Winona
| Type | Count |
|---|---|
| Hotels | 42 |
| Vacation Homes | 39 |
| Cabin Rentals | 33 |
| Holiday Apartments | 15 |
| Cottages | 4 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Winona
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas 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 Winona.
Weather in Winona
View the weather forecast for Winona before booking your Winona 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
Top Attractions Around Winona, MS
Estiavillas offers a large selection of top attractions around Winona. Research things to do on your vacation before you visit Winona.
Winona Country Club
Middleton Cemetery
Montgomery County Performing Arts Center
Grenada Lake
Grenada Country Club
French Camp Academy
Bledsoe Park
Whites Creek Lake Park
Dogwoods Golf Course
The Mississippi Gift Company
Museum of the Mississippi Delta
Back in the Day Museum
University of Mississippi Medical Center - Grenada
Hugh White State Park
Other Places to Stay Near Winona, MS
Winona Vacation Rental Frequently Asked Questions
Which vacation homes in Winona are best for families?
If you are looking for a family-friendly vacation home in Winona, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winona:
How many vacation rentals are available in Winona?
Currently, the total number of properties listed in 2026 is over 136 in the Winona area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winona.
