House
10.0(350 Reviews)
2 Bedrooms
8 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
US $198/Night
7 Nights - US $1,389
Port Bolivar Winter Rentals & Holiday Homes
Discover winter rentals Port Bolivar - We found 1377 exact matches
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Compare Winter Rental in Port Bolivar
10.0
House
10.0(12 Reviews)
4 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $412/Night
7 Nights - US $2,883
Cottage
10.0(1 Review)
1 Bedroom
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $623/Night
7 Nights - US $4,363
House
10.0(66 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
Hot Tub- Parking
- Ocean View
US $319/Night
7 Nights - US $2,232
House
10.0(10 Reviews)
3 Bedrooms
12 Guests
- Parking
View- Air Conditioner
Internet
US $492/Night
7 Nights - US $3,442
House
10.0(48 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $432/Night
7 Nights - US $3,021
House
10.0(7 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
Pool- Ocean View
US $330/Night
7 Nights - US $2,308
House
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $433/Night
7 Nights - US $3,031
US $771/Night
7 Nights - US $5,398
House
10.0(21 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $264/Night
7 Nights - US $1,848
House
10.0(4 Reviews)
3 Bedrooms
14 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $169/Night
7 Nights - US $1,180
House
10.0(17 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $314/Night
7 Nights - US $2,201
House
10.0(4 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $364/Night
7 Nights - US $2,546
House
10.0(13 Reviews)
1 Bedroom
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $290/Night
7 Nights - US $2,030
House
10.0(13 Reviews)
2 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $272/Night
7 Nights - US $1,903
House
10.0(9 Reviews)
2 Bedrooms
7 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $320/Night
7 Nights - US $2,239
Cabin
10.0(7 Reviews)
2 Bedrooms
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $451/Night
7 Nights - US $3,157
House
10.0(6 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $425/Night
7 Nights - US $2,978
Cabin
10.0(5 Reviews)
2 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $321/Night
7 Nights - US $2,244
House
10.0(5 Reviews)
2 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $320/Night
7 Nights - US $2,238
House
10.0(4 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $272/Night
7 Nights - US $1,904
Cabin
10.0(4 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $225/Night
7 Nights - US $1,572
House
10.0(2 Reviews)
1 Bedroom
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $548/Night
7 Nights - US $3,838
House
10.0(2 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $299/Night
7 Nights - US $2,092
About Port Bolivar Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 1377 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 Port Bolivar Winter Rentals
What are the top rated Winter Rentals in Port Bolivar?
There are a lot of options in Port Bolivar. If you plan on staying in the Port Bolivar area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Port Bolivar:
- Dramatic Ocean Views*Seconds to Beach*3 bdrm House*Sleeps 12
- FABULOUS BEACHFRONT! Pets OK-Huge Deck! Lots of space below! Steps to beach
- Splash Spacious 3BD 3bath Beachfront! Steps to Beach!
- 2nd Row Beach House with Beautiful Ocean View and Easy Beach Access
- Beachfront | Hot Tub, Game Room, Mini Golf & More
- "Shore Beats Work" Stunning Home w/Ocean View, Near Beach - 3BR/2BA
- Beachfront | Game Room, Hot Tub & Ocean Views
- Everything Beachy! Beautiful home Close to the Beach
- NEW! Experienced Premier Host! Summer Lovin! Spectacular Views! 3/3 Sleeps 12!
- Beachfront | Decks, Cargo Lift & Ocean Views
How much does it cost to rent a place to stay near Port Bolivar in the wintertime?
The average cost for winter rentals in Port Bolivar is $483 per night. Casai has a wide list of great winter places to stay near Port Bolivar that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Port Bolivar that allow pets?
Yes, here are the top cottage/chalet rentals in Port Bolivar that allow you to bring your pet or dog:
- Sandy Blue Heaven– Beach Getaway with Huge Deck great for families! Pet friendly
- BEACHFRONT with DECK Hot Tub and View and Cargo Lift Sleeps 14
- Retreat w/Hot Tub & Fenced Yard: Walk to Beach
- Newly Enlarged Cozy Cottage-5 Min. walk to the beach. Great Gulf Views!
See all pet-friendly vacation rentals in Port Bolivar on Casai.com
Do you have any winter rentals in Port Bolivar that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Port Bolivar to find what works for you.
Are there winter accommodations in Port Bolivar that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 1377 private swimming pools or indoor pools accommodations near Port Bolivar along with other great amenities.
Do any winter holiday rentals in Port Bolivar have hot tubs?
About 1377 holiday rentals in Port Bolivar boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Port Bolivar?
Yes, there are many luxury places to stay in Port Bolivar for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Port Bolivar with all the best amenities for your next trip.
