143+ Private Villas and Holiday Rentals in Winona |
Winona Holiday Rentals
House
- Mississippi
- ·
- Coffeeville
- 7.00 mi to center
10.0Exceptional
(40 Reviews)
2 Bedrooms
2 Baths
8 Guests
Fireplace/Heating
Pet Friendly
Kitchen
Air Conditioner
د.إ.1,348/Night
7 Nights - د.إ.9,435
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
15 Guests
Balcony/Terrace
Parking- Air Conditioner
Internet
د.إ.1,983/Night
7 Nights - د.إ.13,882
Hotel
- Mississippi
- ·
- Grenada
- 0.85 mi to center
9.0Exceptional
(689 Reviews)
1 Bath
Pool
Breakfast- Kitchen
- Parking
د.إ.543/Night
7 Nights - د.إ.3,797
House
- Mississippi
- ·
- Scobey
- 4.49 mi to center
10.0Exceptional
(33 Reviews)
4 Bedrooms
2 Baths
8 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.634/Night
7 Nights - د.إ.4,436
House
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
7 Guests
1248.61 ft²
Spa- Fireplace/Heating
- Parking
- Internet
د.إ.739/Night
7 Nights - د.إ.5,171
Apartment
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.356/Night
7 Nights - د.إ.2,490
House
- Mississippi
- ·
- Tie Plant
- 1.03 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
7 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.665/Night
7 Nights - د.إ.4,653
Cabin
- Mississippi
- ·
- Elliott
- 7.59 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
7 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.876/Night
7 Nights - د.إ.6,133
Cabin
- Mississippi
- ·
- Coffeeville
- 5.99 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.888/Night
7 Nights - د.إ.6,218
Luxury Holiday Rentals in Winona
Over 134+ Luxury Holiday Rentals in or Near Winona
Apartment
- Mississippi
- ·
- Grenada
- 0.62 mi to center
3 Bedrooms
2 Baths
7 Guests
Child Friendly
Security/Safety
د.إ.13,754/Night
7 Nights - د.إ.96,275
Apartment
- Mississippi
- ·
- Kosciusko
- 4.79 mi to center
3 Bedrooms
2 Baths
7 Guests
- Child Friendly
- Security/Safety
د.إ.12,185/Night
7 Nights - د.إ.85,294
House
- Mississippi
- ·
- Coffeeville
- 4.60 mi to center
9.4Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
14 Guests
- Pet Friendly
- Child Friendly
- Security/Safety
د.إ.2,222/Night
7 Nights - د.إ.15,553
House
- Mississippi
- ·
- Elliott
- 5.13 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
د.إ.1,718/Night
7 Nights - د.إ.12,027
House
- Mississippi
- ·
- Coila
- 18.58 mi to center
3 Bedrooms
2 Baths
8 Guests
1905.21 ft²
- Fireplace/Heating
View- Pet Friendly
- Parking
د.إ.1,616/Night
7 Nights - د.إ.11,311
House
8.0Excellent
(2 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
د.إ.1,601/Night
7 Nights - د.إ.11,208
New
House
3 Bedrooms
4 Baths
8 Guests
4200 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
د.إ.1,507/Night
7 Nights - د.إ.10,547
House
- Mississippi
- ·
- Lexington
- 0.66 mi to center
3 Bedrooms
2 Baths
8 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,488/Night
7 Nights - د.إ.10,415
House
- Mississippi
- ·
- Grenada
- 1.10 mi to center
9.4Exceptional
(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,387/Night
7 Nights - د.إ.9,710
Top-Rated Holiday Rentals with a Pool in Winona
Over 26+ The Best Private Villas and Holiday Rentals in Winona with a Pool
Cabin
- Mississippi
- ·
- Tie Plant
- 2.76 mi to center
9.6Exceptional
(146 Reviews)
3 Bedrooms
3 Baths
8 Guests
2500 ft²
Private Pool
Hot Tub- Spa
- Fireplace/Heating
د.إ.978/Night
7 Nights - د.إ.6,849
Hotel
- Mississippi
- ·
- Grenada
- 0.89 mi to center
8.6Fabulous
(586 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
د.إ.586/Night
7 Nights - د.إ.4,102
Hotel
- Mississippi
- ·
- Grenada
- 0.85 mi to center
8.5Fabulous
(153 Reviews)
1 Bath
305.7 ft²
Oceanfront- Hot Tub
- Fireplace/Heating
- Pool
د.إ.760/Night
7 Nights - د.إ.5,321
Hotel
8.4Excellent
(531 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
د.إ.639/Night
7 Nights - د.إ.4,469
Hotel
8.3Excellent
(223 Reviews)
2 Baths
355.21 ft²
- Oceanfront
- Fireplace/Heating
- Pool
Ocean View
د.إ.498/Night
7 Nights - د.إ.3,485
Hotel
8.2Excellent
(713 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
د.إ.521/Night
7 Nights - د.إ.3,647
Hotel
8.2Excellent
(694 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
د.إ.516/Night
7 Nights - د.إ.3,614
Hotel
8.2Excellent
(519 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.590/Night
7 Nights - د.إ.4,128
Hotel
8.0Excellent
(468 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.396/Night
7 Nights - د.إ.2,773
Pet-Friendly Holiday Rentals in Winona
Over 39+ Pet-Friendly Holiday Rentals in or Near Winona
Cabin
- Mississippi
- ·
- Tie Plant
- 4.19 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
240 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.770/Night
7 Nights - د.إ.5,391
House
- Mississippi
- ·
- Coffeeville
- 2.75 mi to center
9.5Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1819.1 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
د.إ.1,103/Night
7 Nights - د.إ.7,720
Hotel
- Mississippi
- ·
- Durant
- 4.03 mi to center
6.0Good
(8 Reviews)
1 Bath
- Breakfast
- Pet Friendly
- Kitchen
- Parking
د.إ.275/Night
7 Nights - د.إ.1,924
Cabin
- Mississippi
- ·
- Coffeeville
- 4.76 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.574/Night
7 Nights - د.إ.4,018
House
2 Bedrooms
2 Baths
4 Guests
204.51 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.463/Night
7 Nights - د.إ.3,239
Cabin
- Mississippi
- ·
- Tie Plant
- 4.26 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,301/Night
7 Nights - د.إ.9,108
Cabin
- Mississippi
- ·
- Coffeeville
- 4.61 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Child Friendly
- Laundry
- Security/Safety
د.إ.574/Night
7 Nights - د.إ.4,018
Cabin
- Mississippi
- ·
- Avalon
- 7.72 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.530/Night
7 Nights - د.إ.3,713
Cabin
- Mississippi
- ·
- Coffeeville
- 4.97 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.574/Night
7 Nights - د.إ.4,018
Large Holiday Rentals and Private Villas in Winona
Over 6+ Large Holiday Rentals and Private Villas in or Near Winona
Cabin
- Mississippi
- ·
- Coffeeville
- 2.75 mi to center
9.4Exceptional
(51 Reviews)
3 Bedrooms
2 Baths
100 Guests
1815 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
د.إ.1,013/Night
7 Nights - د.إ.7,088
Cabin
- Mississippi
- ·
- Grenada
- 0.95 mi to center
5.6Average
(12 Reviews)
63 Bedrooms
1 Bath
20 Guests
301.39 ft²
- Pool
- Parking
- Air Conditioner
- Internet
د.إ.318/Night
7 Nights - د.إ.2,229
House
- Mississippi
- ·
- Grenada
- 2.92 mi to center
8.4Excellent
(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.831/Night
7 Nights - د.إ.5,817
House
1 Bedroom
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
د.إ.567/Night
7 Nights - د.إ.3,970
House
- Mississippi
- ·
- Coffeeville
- 6.81 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
د.إ.2,161/Night
7 Nights - د.إ.15,131
House
- Mississippi
- ·
- Durant
- 4.98 mi to center
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
د.إ.421/Night
7 Nights - د.إ.2,945
Wheelchair Accessible Holiday Homes in Winona
Over 7+ Wheelchair Accessible Holiday Homes in or Near Winona
Hotel
8.1Excellent
(354 Reviews)
10 Baths
356.29 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
د.إ.485/Night
7 Nights - د.إ.3,393
Hotel
- Mississippi
- ·
- Grenada
- 1.49 mi to center
8.0Excellent
(813 Reviews)
1 Bath
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
د.إ.499/Night
7 Nights - د.إ.3,493
Hotel
7.7Very Good
(142 Reviews)
8 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Pet Friendly
د.إ.459/Night
7 Nights - د.إ.3,213
Hotel
4.6Average
(103 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.287/Night
7 Nights - د.إ.2,005
Hotel
7.7Very Good
(126 Reviews)
5 Baths
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.257/Night
7 Nights - د.إ.1,800
Hotel
- Mississippi
- ·
- Grenada
- 1.23 mi to center
4.8Average
(163 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
د.إ.1,833/Night
7 Nights - د.إ.12,828
Hotel
7.5Very Good
(106 Reviews)
1 Bath
322.92 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Parking
د.إ.534/Night
7 Nights - د.إ.3,742
Winona Private Villas and Holiday Homes Under $200
Over 69+ Winona Private Villas and Holiday Homes Under $200
House
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1600 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
د.إ.652/Night
7 Nights - د.إ.4,561
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
172.22 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
د.إ.569/Night
7 Nights - د.إ.3,981
Hotel
- Mississippi
- ·
- Grenada
- 0.96 mi to center
8.0Excellent
(238 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
د.إ.331/Night
7 Nights - د.إ.2,317
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
3 Guests
400 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.423/Night
7 Nights - د.إ.2,960
House
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
د.إ.514/Night
7 Nights - د.إ.3,599
Cabin
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Child Friendly
د.إ.685/Night
7 Nights - د.إ.4,793
Cabin
- Mississippi
- ·
- Coffeeville
- 4.65 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.574/Night
7 Nights - د.إ.4,018
Cabin
- Mississippi
- ·
- Coffeeville
- 2.18 mi to center
9.8Exceptional
(48 Reviews)
1 Bedroom
1 Bath
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.537/Night
7 Nights - د.إ.3,761
Apartment
9.8Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.621/Night
7 Nights - د.إ.4,348
Instantly Bookable Holiday Homes in Winona
Over 41+ Instantly Bookable Holiday Homes in or Near Winona
Cabin
- Mississippi
- ·
- Elliott
- 9.77 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
د.إ.912/Night
7 Nights - د.إ.6,383
Cabin
- Mississippi
- ·
- Tie Plant
- 4.44 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pet Friendly
- Air Conditioner
- Child Friendly
- Laundry
د.إ.496/Night
7 Nights - د.إ.3,471
Cabin
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
- Laundry
د.إ.1,141/Night
7 Nights - د.إ.7,988
House
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,106/Night
7 Nights - د.إ.7,742
Cottage
- Mississippi
- ·
- Grenada
- 2.76 mi to center
9.8Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
د.إ.1,348/Night
7 Nights - د.إ.9,435
Apartment
- Mississippi
- ·
- Grenada
- 1.23 mi to center
9.8Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
2400 ft²
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
د.إ.884/Night
7 Nights - د.إ.6,188
Cabin
- Mississippi
- ·
- Tie Plant
- 4.29 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.669/Night
7 Nights - د.إ.4,682
Cabin
- Mississippi
- ·
- Tie Plant
- 4.26 mi to center
9.6Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.1,026/Night
7 Nights - د.إ.7,180
Cabin
- Mississippi
- ·
- Coffeeville
- 4.57 mi to center
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.912/Night
7 Nights - د.إ.6,383
Book a Last Minute Place to Stay in Winona
About Casai's Private Villas and Holiday Rentals in Winona
Discover more than 143 vacation rentals available in Winona. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winona.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winona, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winona. On average, places to stay near Winona offer 403.12 ft², with nightly prices averaging د.إ.939.
With Casai, finding and comparing holiday rentals in Winona is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Winona
| Type | Count |
|---|---|
| Vacation Homes | 45 |
| Holiday Apartments | 15 |
| Cottages | 4 |
Use these Quick Filters to Find a Holiday Rental in Winona
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winona.
Weather in Winona, MS
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
Casai offers a large selection of top attractions around Winona . Research things to do on your vacation before you visit Winona.
Other Places to Stay in Winona, MS
Frequently Asked Questions About Winona?
What are the top holiday rentals in Winona?
With numerous options available in Winona, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winona:
- BIG OAKS LODGE New Lodge! 3 bedroom, 3 1/2 baths, full kitchen and laundry.
- Cabin in the woods overlooking Grenada lake.
- Bougie Residence in a Country Setting near Enid and Grenada Lake
- Fishing, Family, Ballgames, Work or Vacation! Cozy Cottage near Grenada Lake
- Modern Greenwood Studio < 1 Mi to Downtown!
- Lida's Place - 3 BR 2 BA Ranch House - 7.6 miles to Grenada Lake
- 5 min. from Grenada Lake! 3 bed room/Outside pavilion/Family size/fire pit
- Minutes away from one of the greatest crappie fishing lakes in the world
- 2bedroom cabin with AC,Heat,WiFi in Gore Springs just 2.6 miles to Grenada lake
- The most unique getaway experience in North Mississippi!
Which holiday homes in Winona are best for families?
If you're searching for a family-friendly holiday home in Winona, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winona:
How many Casai.ae holiday rentals are available in Winona?
As of 2026, Casai boasts over 143 properties listed in the Winona area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winona.
People Also Ask
Finding the best prices in Winona
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