Vacation rentals in Southside, Jacksonville

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Top-rated vacation rentals in Southside, Jacksonville

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Superhost

Apartment in Amelia island

4.93 out of 5 average rating, 15 reviews

AIP Resort,LUX Oceanfront,Fully Renovated,

Experience the epitome of coastal luxury in this 2BR, 2BA retreat with panoramic ocean views and high-end finishes. This newly remodeled villa offers a serene beach ambiance with a comfortable oceanfront living room with a smart TV.The gourmet kitchen features a quartz island, stainless steel appliances, and leads to a dining area for four, with a convenient laundry nook. Enjoy a private terrace with ocean breezes and two chic bedrooms, each with plush beds, storage, smart TVs, and private baths

Superhost

An outdoor seating area features a large sectional sofa with blue and white stripes, positioned near a wooden dining table. Lush greenery and sand dunes extend in the background, with a securely fenced area ensuring privacy.

Condo in Beaches

4.83 out of 5 average rating, 107 reviews

Our Hawaiian Bliss just steps from the Beach!

Enjoy this small, gated, oceanfront condo community just steps from the Ocean w/oceanfront pool, oceanfront communal deck with outdoor furniture for you to enjoy w/private beach access. Our 1 BR condo sleeps 5 comfortably w/queen bed & twin trundle bed upstairs, full size sleeper sofa downstairs. 2 full baths, one upstairs w/walk-in shower and one downstairs w/tub/shower. Slight view of the ocean from upstairs balcony & there is a nice downstairs patio area in front of condo for your enjoyment!

Guest favorite

A modern kitchen features white cabinetry, sleek stainless steel appliances, and a large quartz countertop with seating for three. Natural light enters through a window, illuminating the space. A minimalist design is complemented by decorative elements, creating an inviting area for cooking and gathering.

Home in Jacksonville

5 out of 5 average rating, 22 reviews

Updated Home | Stadium | Beaches | Downtown | Zoo

Come unwind and relax in our quite brick home with modern updates. Plenty of parking for boats, RV, trailers N' toys! Gorgeous updated private home in Jacksonville near trout river in a super quiet and tucked away neighborhood. Nice wooded area gives this home a country vibe! Nice size yard for kids to play in. Centrally located with easy access to the interstate. Zoo - 2 mins Downtown - 10 mins Airport - 10 mins Beach - 20-30 mins Amelia Island/Fernandina - 40 mins Saint Augustine - 55 mins

Guest favorite

A modern living room features light grey leather sofas with built-in charging stations. A rectangular coffee table is placed on a textured blue area rug, while a floor lamp provides illumination. A doorway leads to a separate area, adding depth to the space.

Home in Southwest Jacksonville

4.92 out of 5 average rating, 25 reviews

Tasteful 3/2 vacation rental

This modern and beautiful vacation home offers guest space, comfort, and luxury. The home has a 3 bedrooms 2 full bathrooms, master suite offers a private bathroom. Fully equipped kitchen, living room, and separate family room with a Q size pull out sofa. Features also include WiFi and 2 Samsung 65’ inch smart tv’s with surround sound attached to each. We do our best to make this place cozy so you can have a great and comfortable time with your family. Leather sofas include charging station.

Guest favorite

Townhouse in St. Augustine

4.91 out of 5 average rating, 132 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

Come and escape to the Florida sun and beaches at Paradise Retreat! This completely renovated home is only a few minute's walk to the beach with access to miles of tranquil, quiet stretches of beautiful sand, abundant sea seashells and a fantastic blue ocean. It is located in a quiet residential neighborhood, perfect for bike riding and evening walks under the stars. Paradise Retreat is your peaceful getaway only minutes to everything Vilano Beach and historic Saint Augustine has to offer.

Guest favorite

Villa in Jacksonville

4.88 out of 5 average rating, 102 reviews

Country villa pool hot tub game rm pond 2.5 acres

Take it easy at this unique and tranquil getaway. Ask about our couples discount. Our villa includes pond, pool, hot tub, game room, outdoor cooking area with industrial smoker, wood burning pizza oven, and gas grill. Oyster bar, fire pit area wood included. Kitchen has 2 coffee making options, air cooker and all other essentials. Full laundry with soap and dryer sheets. Parking space for your toys and camper. Security gate w/ fence completely surrounding the property.

Top guest favorite

A wooden dock extends over calm waters, framed by lush greenery on both sides. Two bench seating areas, built with natural wood, provide spaces for relaxation while taking in the tranquil surroundings. The scene is complemented by a clear blue sky overhead.

Home in Fernandina Beach

5 out of 5 average rating, 33 reviews

WOW* Beach* Pool* Golf Bungalow!

The perfect island getaway. Located within the Omni resort, and newly remodeled with a bright and airy boho theme, this spacious retreat is a place of pure peace. Within steps of two community pools, on-site golf course, and private beach - which is less than a half a mile away. Completely remodeled and sparkling clean. Beautiful, fully stock kitchen with two bedrooms, two full bathrooms and a warm, comfortable living room with a large TV and electric fireplace.

Guest favorite

A spacious outdoor patio area features a ceiling with wooden beams and overhead fans. Two hanging chairs provide seating, while a stylish seating arrangement is visible. A heated pool is situated in the background, complemented by a manicured turf area and a shaded umbrella.

Home in Beaches

5 out of 5 average rating, 6 reviews

Family Beach Getaway w/ Pool & Sports Playground

Welcome to your Family Tides' perfect coastal escape - managed exclusively by Welcome Home Rentals Jax Beach. Just 6 blocks from the beach, this 4-bedroom, 2-bathroom vacation rental is the perfect escape. It features a large backyard with a heated pool for relaxation and a dedicated golf chipping course along with a mini football turf field for fun and games. This charming getaway is ideal for creating unforgettable memories with family and friends!

Top guest favorite

The houseboat features a spacious deck adorned with two lounge chairs and a large umbrella for shade. The deck area is surrounded by water and boats, showcasing a vibrant outdoor space designed for relaxation and enjoyment.

Boat in Orange Park

4.96 out of 5 average rating, 28 reviews

Houseboat - Boatiful Life

Island Life by It’s A Boatiful Life is a one of a kind getaway! A lovely space to unwind and allow your everyday worries to “float” away. This is truly water living at it’s best! Nestled in between the city and the country, the boat is perfect for a nice escape and home base for unique shops, excellent restaurants, community events and the Sunset Tiki Bar right on site. The island's location is ideal for small city outings to big city nightlife.

Guest favorite

A wooden pier extends over calm blue waters, inviting visitors to stroll along its length. People can be seen enjoying the ocean view, while a small beach umbrella provides shade. The clear sky above complements the serene coastal scene.

Condo in Beaches

4.82 out of 5 average rating, 110 reviews

Fun in the Sun - OCEAN FRONT!

Keep it simple at this peaceful beach studio! Yes, it is 100% ocean front with only some grass and sand separating you from the water! With the pool and the beach just steps outside your door "fun in the sun" is always the best choice! Also, within a short walking distance, are all the great restaurants and nightlife the beach has to offer! Don't miss out on one of the best beach areas in Florida!

Guest favorite

Home in Beaches

4.94 out of 5 average rating, 251 reviews

2 Kings + 2 bunks, Walk to Beach - $0 Host fee

This 2-story 3 BR/2.5bath, 1700 sq ft. elegantly furnished vacation beach house is within 3 blocks to the beach, restaurants, grocery, and shopping. Experience melting into TWO TempurPedic king beds, enjoy a refreshing multijet spa shower, sip coffee or drinks on the large master balcony, or zen garden patio, or watch various prepaid streaming apps on multiple large 4k TVs throughout the house.

Superhost

A private balcony is showcased with outdoor seating, offering a round table and two comfortable chairs. The oceanfront view reveals the sandy beach and clear blue sky, creating a serene seaside atmosphere.

Condo in Fernandina Beach

4.75 out of 5 average rating, 4 reviews

Sunrise Shores~insane view

Introducing our brand new listing, unveiled in January 2025. If you're wondering about the lack of reviews, we are just listed and have not yet hosted anyone. I do have other properties that I host so please check out my host review to feel more confident in booking. Our spacious condo is designed to provide a home-like comfort while indulging you with a luxurious resort ambiance.