Estia Villas - Vacation Rentals in Winona
Apartment
10.0
(
67 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
269 ft²
-
Kitchen -
Air Conditioner -
Internet -
Child Friendly
US $71
/Night
7 Nights - $498
Apartment
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
15 Guests
-
Parking -
Balcony/Terrace -
Air Conditioner
-
Internet
US $540
/Night
7 Nights - $3,780
US $141
/Night
7 Nights - $985
Apartment
10.0
(
64 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
280 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
TV
US $120
/Night
7 Nights - $839
Apartment
10.0
(
57 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
280 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $110
/Night
7 Nights - $769
Apartment
10.0
(
52 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
280 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $120
/Night
7 Nights - $839
Apartment
10.0
(
48 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
280 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $110
/Night
7 Nights - $769
House
10.0
(
43 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
-
Kitchen
-
Air Conditioner
-
Pet Friendly -
Laundry
US $367
/Night
7 Nights - $2,569
See More Winona Vacation Rentals
Luxury Places to Stay in Winona
Over 131+
Luxury Places to Stay in or Near Winona
US $2,255
/Night
7 Nights - $15,783
US $1,381
/Night
7 Nights - $9,667
House
8.6
(
4 Reviews
)
4 Bedrooms
3 Bathrooms
14 Guests
-
Pet Friendly
-
Child Friendly
-
Security/Safety
US $604
/Night
7 Nights - $4,228
House
8.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $436
/Night
7 Nights - $3,052
Cabin
1 Bedroom
1 Bathroom
4 Guests
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $431
/Night
7 Nights - $3,017
House
10.0
(
52 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $424
/Night
7 Nights - $2,966
Cabin
2 Bedrooms
1 Bathroom
4 Guests
240 ft²
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
US $385
/Night
7 Nights - $2,697
New
House
2 Bedrooms
2 Bathrooms
7 Guests
2300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $373
/Night
7 Nights - $2,614
See More Winona Luxury Vacation Rentals
Find More Winona Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Winona
Over 23+
Top-Rated Vacation Rentals with a Pool in or Near Winona
Hotel
8.6
(
602 Reviews
)
-
Breakfast -
Parking
-
Pool -
Kitchen
US $173
/Night
7 Nights - $1,209
US $184
/Night
7 Nights - $1,285
Hotel
8.4
(
561 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $179
/Night
7 Nights - $1,255
Hotel
8.4
(
206 Reviews
)
355.21 ft²
-
Oceanfront -
Parking
-
Pool
-
Ocean View
US $136
/Night
7 Nights - $949
Hotel
8.2
(
768 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
US $142
/Night
7 Nights - $993
Hotel
8.2
(
736 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $124
/Night
7 Nights - $870
US $159
/Night
7 Nights - $1,110
US $108
/Night
7 Nights - $755
See More Winona Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Winona
Over 34+
Pet-Friendly Vacation Rentals in or Near Winona
Cabin
10.0
(
13 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $312
/Night
7 Nights - $2,187
House
9.5
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1819.1 ft²
-
Parking
-
Balcony/Terrace
-
Internet
-
Pet Friendly
US $300
/Night
7 Nights - $2,102
US $75
/Night
7 Nights - $524
Cabin
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $353
/Night
7 Nights - $2,472
Cabin
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
240 ft²
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
US $319
/Night
7 Nights - $2,232
Cabin
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $137
/Night
7 Nights - $959
Cabin
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Pet Friendly
-
Child Friendly
-
Laundry
-
Security/Safety
US $156
/Night
7 Nights - $1,094
Cabin
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Pet Friendly
-
Laundry
US $156
/Night
7 Nights - $1,094
See More Pet-Friendly Vacation Rentals in Winona on PetFriendly.io
Large Vacation Homes & Villas in Winona
Over 5+
Large Vacation Homes & Villas in or Near Winona
House
9.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1250 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $311
/Night
7 Nights - $2,180
Cabin
5.9
(
13 Reviews
)
63 Bedrooms
1 Bathroom
20 Guests
301.39 ft²
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $87
/Night
7 Nights - $607
House
10.0
(
4 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
-
Hot Tub
-
Parking
-
Pool
-
Kitchen
US $589
/Night
7 Nights - $4,120
Cabin
9.4
(
52 Reviews
)
3 Bedrooms
2 Bathrooms
100 Guests
1815 ft²
-
Parking
-
Balcony/Terrace
-
View -
Kitchen
US $280
/Night
7 Nights - $1,958
House
4 Bedrooms
3 Bathrooms
10 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Laundry
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
Hotel
7.7
(
316 Reviews
)
356.29 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $143
/Night
7 Nights - $998
US $139
/Night
7 Nights - $975
Hotel
7.7
(
142 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Air Conditioner
US $103
/Night
7 Nights - $719
Hotel
4.6
(
105 Reviews
)
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $78
/Night
7 Nights - $546
Hotel
7.7
(
126 Reviews
)
204.51 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
US $70
/Night
7 Nights - $490
US $499
/Night
7 Nights - $3,493
Hotel
7.5
(
106 Reviews
)
322.92 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Air Conditioner
US $151
/Night
7 Nights - $1,056
Winona Vacation Rentals and Airbnb Places to Stay Under $200
Over 57+
Winona Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
14 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
400 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $161
/Night
7 Nights - $1,127
House
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
6 Guests
1302.43 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $140
/Night
7 Nights - $980
US $80
/Night
7 Nights - $560
Apartment
10.0
(
5 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
400 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $174
/Night
7 Nights - $1,217
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $186
/Night
7 Nights - $1,305
Cabin
9.8
(
7 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Pet Friendly
-
Laundry
US $156
/Night
7 Nights - $1,094
Cabin
9.6
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Pet Friendly
-
Child Friendly
US $156
/Night
7 Nights - $1,094
Apartment
1 Bedroom
1 Bathroom
2 Guests
190 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $123
/Night
7 Nights - $858
See More Winona Vacation Rental Deals
Instantly Bookable Vacation Homes in Winona
Over 42+
Instantly Bookable Vacation Homes in or Near Winona
House
10.0
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $337
/Night
7 Nights - $2,359
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Air Conditioner
-
Pet Friendly
-
Child Friendly
-
Laundry
US $135
/Night
7 Nights - $945
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $360
/Night
7 Nights - $2,520
New
Cabin
10.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $308
/Night
7 Nights - $2,159
House
9.8
(
35 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $241
/Night
7 Nights - $1,689
Apartment
9.8
(
10 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $246
/Night
7 Nights - $1,719
Cabin
9.6
(
18 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $284
/Night
7 Nights - $1,985
Cabin
9.6
(
5 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $251
/Night
7 Nights - $1,760
See More Winona Short-Term Vacation Rentals
About Winona Vacation Rentals
With more than 140 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 373.37 ft² on average, with prices averaging US $245 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 | 41 |
| Vacation Homes | 40 |
| Cabin Rentals | 31 |
| Holiday Apartments | 21 |
| 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 140 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.
