House
10.0(17 Reviews)
2 Bedrooms
13 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $344/Night
7 Nights - US $2,405
Okeechobee Winter Rentals & Holiday Homes
Discover winter rentals Okeechobee - We found 91 exact matches
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Compare Winter Rental in Okeechobee
10.0
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
View- Air Conditioner
US $313/Night
7 Nights - US $2,190
US $200/Night
7 Nights - US $1,400
House
10.0(5 Reviews)
2 Bedrooms
4 Guests
Hot Tub- Parking
Pool
Ocean View
US $463/Night
7 Nights - US $3,240
House
7.7(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
Internet
Child Friendly
US $187/Night
7 Nights - US $1,309
Cabin
10.0(1 Review)
1 Bedroom
2 Guests
- Internet
Pet Friendly- Child Friendly
Bedding/Linens
US $498/Night
7 Nights - US $3,483
House
7.5(2 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- View
- Air Conditioner
US $529/Night
7 Nights - US $3,702
Cabin
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $299/Night
7 Nights - US $2,096
House
7.1(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Internet
- Pet Friendly
US $174/Night
7 Nights - US $1,218
Cabin
9.8(93 Reviews)
2 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $267/Night
7 Nights - US $1,870
House
1.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Internet
US $229/Night
7 Nights - US $1,603
Cabin
9.8(6 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $229/Night
7 Nights - US $1,603
House
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Internet
US $648/Night
7 Nights - US $4,538
Cabin
9.6(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $323/Night
7 Nights - US $2,260
Cabin
9.4(56 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $294/Night
7 Nights - US $2,057
Cabin
9.4(17 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $234/Night
7 Nights - US $1,635
Cabin
9.2(26 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $212/Night
7 Nights - US $1,482
Cabin
8.8(10 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $270/Night
7 Nights - US $1,893
Cabin
8.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $254/Night
7 Nights - US $1,776
Cabin
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $264/Night
7 Nights - US $1,851
Cabin
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,832
Cabin
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $262/Night
7 Nights - US $1,832
Cabin
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $188/Night
7 Nights - US $1,317
US $156/Night
7 Nights - US $1,093
About Okeechobee Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 91 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Okeechobee Winter Rentals
What are the top rated Winter Rentals in Okeechobee?
There are a lot of options in Okeechobee. If you plan on staying in the Okeechobee area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Okeechobee:
- Pool, Hot tub, Kid & Pet Friendly! Near Lake, CLEAN
- Pet friendly, fenced acres, oak hammock, and lake. Star gazing. Peaceful.
- NEW! Cozy and Relaxing Fishing Retreat
- The Ultimate Lake Okeechobee Fishing Retreat
- Private Hot Tub! Home < 1 Mi to Lake Okeechobee
- Walk to Scenic Trails: Waterfront Okeechobee Oasis
- Redneck Riviera ,fishing relaxing paradise On canal , very close to locks
- The Fish House Fl vacation home
- Boat Dock & Yard: Waterfront Okeechobee Retreat
- Pet Friendly 3 Bed 2 bath Family Home on the Water
How much does it cost to rent a place to stay near Okeechobee in the wintertime?
The average cost for winter rentals in Okeechobee is $315 per night. Casai has a wide list of great winter places to stay near Okeechobee that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Okeechobee that allow pets?
Yes, here are the top cottage/chalet rentals in Okeechobee that allow you to bring your pet or dog:
- Cozy cottage on 8 acres near state park and atv trails. Pet Friendly!
- Twins Red Cabin Escape
- Twin Palms Resort
- Beautiful 2/2 townhome across from world class Lake Okeechobee Bass fishing !
See all pet-friendly vacation rentals in Okeechobee on Casai.com
Do you have any winter rentals in Okeechobee that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Okeechobee to find what works for you.
Are there winter accommodations in Okeechobee that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 91 private swimming pools or indoor pools accommodations near Okeechobee along with other great amenities.
Do any winter holiday rentals in Okeechobee have hot tubs?
About 91 holiday rentals in Okeechobee boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Okeechobee?
Yes, there are many luxury places to stay in Okeechobee for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Okeechobee with all the best amenities for your next trip.
