Apartment
9.8(43 Reviews)
3 Bedrooms
6 Guests
Oceanfront
Hot Tub
Parking
Pool
US $160/Night
7 Nights - US $1,122
Side Harbor Winter Rentals & Holiday Homes
Discover winter rentals Side Harbor - We found 151 exact matches
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Compare Winter Rental in Side Harbor
9.8
US $559/Night
7 Nights - US $3,911
Apartment
6.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Pool
Spa
Ocean View
US $179/Night
7 Nights - US $1,255
Apartment
9.7(7 Reviews)
2 Bedrooms
6 Guests
Balcony/Terrace
View
Air Conditioner
Internet
US $94/Night
7 Nights - US $661
Apartment
10.0(6 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $62/Night
7 Nights - US $431
Resort
9.5(650 Reviews)
27 Guests
Private Pool- Oceanfront
- Hot Tub
Breakfast
US $324/Night
7 Nights - US $2,265
Apartment
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $90/Night
7 Nights - US $629
Apartment
9.5(349 Reviews)
14 Bedrooms
32 Guests
Private Beach- Oceanfront
- Breakfast
- Parking
US $62/Night
7 Nights - US $435
Apartment
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Spa
US $95/Night
7 Nights - US $666
Apartment
9.5(15 Reviews)
3 Bedrooms
10 Guests
- Private Beach
- Oceanfront
- Hot Tub
- Breakfast
US $34/Night
7 Nights - US $238
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Spa
US $84/Night
7 Nights - US $591
US $164/Night
7 Nights - US $1,147
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Breakfast
- Parking
- Pool
- Ocean View
US $54/Night
7 Nights - US $378
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Spa
US $125/Night
7 Nights - US $874
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $100/Night
7 Nights - US $702
Apartment
10.0(1 Review)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $86/Night
7 Nights - US $603
Apartment
9.8(47 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $91/Night
7 Nights - US $637
Apartment
9.8(16 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $87/Night
7 Nights - US $610
Apartment
9.8(10 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $74/Night
7 Nights - US $517
Villa
9.6(17 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $146/Night
7 Nights - US $1,020
Apartment
8.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $97/Night
7 Nights - US $677
Apartment
7.4(6 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $125/Night
7 Nights - US $873
Villa
6.0(1 Review)
5 Bedrooms
10 Guests
- Hot Tub
- Pool
- Spa
- Ocean View
US $176/Night
7 Nights - US $1,231
About Side Harbor Winter Rental on Casai.nz
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 151 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.
Frequently Asked Questions About Side Harbor Winter Rentals
What are the top rated Winter Rentals in Side Harbor?
There are a lot of options in Side Harbor. If you plan on staying in the Side Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Side Harbor:
- Akra Sorgun Tui Blue Sensatori - All Inclusive
- Akra Sorgun Tui Blue Sensatori - Ultra All Inclusive
- TUI Blue Barut Andız - All Inclusive - Adults Only
- Nephos Beach Hotel
- Arum Barut Collection - Ultra All Inclusive
- 6 Rooms By Zula
- Calimera Side Resort - All inclusive
- Sueno Hotels Beach Side
- Melas Resort Hotel
- Voyage Sorgun
How much does it cost to rent a place to stay near Side Harbor in the wintertime?
The average cost for winter rentals in Side Harbor is $224 per night. Casai has a wide list of great winter places to stay near Side Harbor that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Side Harbor that allow pets?
Yes, here are the top cottage/chalet rentals in Side Harbor that allow you to bring your pet or dog:
- LUXURY APARTMENT | SIDE | CLOSE TO SEA | JACCUZI ON TERRACE | CHILD FRIENDLY |
- BIJAL
- Barut Hemera - Ultra All Inclusive
- TROPICANA G 2, 2 bed ground floor home on corner position in a 5 star community
See all pet-friendly vacation rentals in Side Harbor on Casai.nz
Do you have any winter rentals in Side Harbor that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Side Harbor to find what works for you.
Are there winter accommodations in Side Harbor that have indoor swimming pools?
As of 2026, the data from Casai.nz shows that there are over 151 private swimming pools or indoor pools accommodations near Side Harbor along with other great amenities.
Do any winter holiday rentals in Side Harbor have hot tubs?
About 151 holiday rentals in Side Harbor boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Side Harbor?
Yes, there are many luxury places to stay in Side Harbor for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Side Harbor with all the best amenities for your next trip.
