Southside Holiday Homes
2050 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $962/Night
For 7 Nights US $6,736
1194.79 ft²
5 Guests
2 Bedrooms
1 Bathroom
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $372/Night
For 7 Nights US $2,602
3000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $642/Night
For 7 Nights US $4,491
1001 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $704/Night
For 7 Nights US $4,929
2303.48 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $773/Night
For 7 Nights US $5,412
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $321/Night
For 7 Nights US $2,244
US $428/Night
For 7 Nights US $2,994
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $139/Night
For 7 Nights US $972
8 Guests
4 Bedrooms
4 Bathrooms
House
- Fireplace/Heating
- Pool
- View
US $650/Night
For 7 Nights US $4,550
850 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $289/Night
For 7 Nights US $2,020
3853.48 ft²
13 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- View
US $1,494/Night
For 7 Nights US $10,458
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- View
US $323/Night
For 7 Nights US $2,264
Why Choose Rent By Owner for your Southside Holiday Homes?
What makes our Holiday Homes special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Southside
How to Book Your Southside Holiday Homes
What's our booking process?
Our platform allows you to browse a curated selection of holiday homes. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Southside
Common Holiday Homes Amenities
What amenities can you expect?
Our Holiday Homes are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Southside, FL
Bel Air
South Olive Park
Southside Holiday Homes Frequently Asked Questions
1. What are the top Holiday Homes in Southside?
There are a lot of options in Southside. If you plan on staying in the Southside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Holiday Homes in Southside:
- 3-Story I Fully Stocked I Designer Interior
- Cozy Fireplace I Heated Pool I Fully Stocked
- New! Resort-style home & heated pool Newly renovated-Great location in SoSo WPB!
- Luxury retreat w/pool & game room
- Boho Bungalow in the Heart of SoSo
- Custom Designed Luxurious Home with Pool in WPB. 5 min from the Beach!
- Palm Beach - Newly Designed come relax, shop, enjoy!
- Stylish - Minutes From Beach, Bars & Eateries
- Home w/heated pool, casita near waterway
- The Sapphire Villa I By Hotel Home Stays
2. How many Holiday Homes are available in Southside?
Currently, the total number of properties listed by RBO in 2026 is over 224 in the Southside area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Southside.
More Rentals You May Like Near Southside
796.53 ft²
16 Guests
8 Bedrooms
4 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $179/Night
For 7 Nights US $1,255
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $204/Night
For 7 Nights US $1,430
1 Guest
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $643/Night
For 7 Nights US $4,500
1600 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $319/Night
For 7 Nights US $2,231
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $363/Night
For 7 Nights US $2,539
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $242/Night
For 7 Nights US $1,694
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
US $118/Night
For 7 Nights US $827
650 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Oceanfront
- Hot Tub
US $216/Night
For 7 Nights US $1,510
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $143/Night
For 7 Nights US $998
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- View
- Pet Friendly
US $152/Night
For 7 Nights US $1,067
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $142/Night
For 7 Nights US $995
470 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Oceanfront
- Hot Tub
US $186/Night
For 7 Nights US $1,299
