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Holiday rentals in Ossabaw Island

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Top-rated holiday rentals in Ossabaw Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious living area is highlighted by a modern ceiling fan and large windows, allowing natural light to fill the space. A comfortable sofa adorned with bright cushions faces a stylish coffee table. A tasteful fireplace sits beneath a television, complementing the neutral color scheme.
Home in Savannah
4.92 out of 5 average rating, 120 reviews

BohoChic Retreat Savannah/PET Friendly/Luxurious

Welcome to our stylish Boho Chic Retreat Savannah! This designer 3-bedroom, 2-bath home offers comfort, convenience, and a touch of Southern hospitality. Whether you're looking to work remotely, explore the city, or simply unwind this retreat has something for everyone. The enclosed yard ensures a safe and enjoyable experience for your fur babies. The garage entertainment space features table tennis, projector with 100" screen, and more. Cooking enthusiasts will love our fully equipped kitchen.

Top guest favourite
A sparkling swimming pool is framed by a white deck, with lounge chairs positioned for relaxation. Lush greenery and colorful plants enhance the outdoor space, while water views extend beyond the pool, highlighting tree-lined edges and a gazebo in the distance.
Home in Midway
4.89 out of 5 average rating, 279 reviews

River Front Getaway; Pool Dock Sunsets Fenced/Dog

Paradise, Rest Relaxation, private, Snowbirds, Adventurers, romantic and small group getaways. A short 35 min distance from cultural and historic destinations in Savannah. Come fall in love with this secluded, quiet island retreat with newly redone pool, hot tub, screen porch. Deep Water Dock, floating dock, moorage, boat launch 1/2 mile away. Start your day with rose colored sunrises and end your day with red splashed sunsets across expansive river and marsh views. Birds, dolphins, fishing

Guest favourite
Home in Savannah
4.79 out of 5 average rating, 118 reviews

Savannah Family Home W/ Game Table

Discover your family’s next favorite getaway in this renovated 3-bed, 2-bath retreat tucked in a quiet corner of the Savannah low county. This home was made for comfort and connection — spacious living areas, a fully equipped kitchen, kids (and grownups!) will love our awesome arcade game table, and backyard is perfect for playtime, grilling out, or simply unwinding under Savannah’s skies. Come for the serenity, stay for the fun. This is the kind of place families go for lasting memories.

Guest favourite
A horse-drawn carriage, with a white wooden cart and large wheels, is shown on a dirt path. Several people sit comfortably inside the carriage, enjoying a day out. Lush green trees provide shade in the background, creating a peaceful country scene.
Farm stay in Savannah
4.95 out of 5 average rating, 241 reviews

Red Gate Farms Hayloft-10 min to Historic Savannah

(STR License # OTC-023578) Family-owned since 1931, Red Gate Farms is a historic hidden gem nestled only 10 min. from downtown Savannah and 30 min. from Tybee Island. Once one of Georgia’s oldest dairy farms but now home to an award-winning event venue, a popular RV park, & many friendly farm animals. The HayLoft offers a peaceful, one-of-a-kind stay with 3 cozy bedrooms, a full kitchen, bathroom, complimentary Wi-Fi, & a large deck perfect for relaxing. We look forward to hosting you!

Top guest favourite
A wooden dock extends into the calm water, leading to a covered gazebo with a red roof. Nearby, a yacht glides smoothly through the river, framed by lush trees in the background. The scene conveys a serene atmosphere ideal for relaxation.
Home in Wilmington Island
4.96 out of 5 average rating, 195 reviews

River House•Dock•King Beds•Nearby Savannah & Tybee

Charming river house with spectacular sunset views, screened in porch for afternoon naps or chats, large outdoor dining space for family dinners & a dock with Adirondack chairs to enjoy the breeze while watching the sailboats & dolphins glide by on the river. Located less than 10 miles from both historic Savannah & Tybee Beach, this home is the perfect place to escape while providing easy access to all your favorite spots! Bring the whole family for some southern sun, fun & relaxation.

Guest favourite
A cozy studio cottage features high wooden ceilings with exposed beams, a swing chair, and colorful accents on the spacious seating area. Large windows invite natural light, while a dining space with white chairs complements the kitchen area, creating a welcoming ambiance.
Home in Midway
4.95 out of 5 average rating, 109 reviews

$129 Cute Date Night Waterfront Cottage Near Sav!

Secluded, Peaceful and Close to Savannah and St Simons!You’ll fall in love with this charming studio cottage from the moment you arrive! Brimming with attention to detail and vintage touches, this 1-bathroom Midway vacation rental is stocked with all the comforts of home and professionally decorated. Our favorite places to dine are: The Sunbury Crab Co, Hunters Cafe, The Salty Cowbow at Shellmans Bluff! There is another cottage on the property that shares outdoor kitchen and pier.

Superhost
Home in Midway
5.0 out of 5 average rating, 3 reviews

Iconic A-Frame Escape with Private Pool

Secluded A-frame on a gorgeous private lot. Enjoy a private pool, outdoor lounging, record player, and a high-end kitchen. 35 minutes from downtown Savannah’s cobblestones and riverfront, and plenty of dining, boating and shopping closer. 3 bedrooms, 1.5 baths. 6 guests max. No parties or outside guests allowed. IMPORTANT: This home is NOT suitable for infants or children under 13 due to steep stairs, unrailed elevated decks, glass architectural features. Pool is NOT heated.

Superhost
A spacious living area features elegant armchairs and a comfortable sofa. A rustic coffee table is situated in front, with light fixtures resembling antlers overhead. Windows allow natural light to illuminate the room, which connects to a dining area visible in the background.
Cottage in Savannah
4.95 out of 5 average rating, 193 reviews

Savannah Cottage - 5 Mi to Wormsloe Historic Site!

Step into a coastal fairytale when you book this whimsical Savannah cottage! Nestled under mature Spanish moss trees, this 2-bed, 1-bath vacation rental has been beautifully renovated to combine modern amenities with historic southern charm, creating the ultimate Georgia paradise! After exploring attractions like Wormsloe Historic Site and Skidaway Island State Park both just a few minutes away, take a drive into town and stroll the streets of the Savannah Historic District!

Guest favourite
A welcoming living area features a leather sofa positioned alongside a wall-mounted TV and a decorative rug. Light wooden flooring complements the blue walls, while windows invite natural light. A dining table with four chairs is visible near the door leading to the outside.
Guest suite in Richmond Hill
4.95 out of 5 average rating, 268 reviews

Pet-Friendly Retreat by the River

Located at the end of 144 Spur and Fort McAllister State Park, across the street from the public launching ramp. Fish Tales Tiki Hut on the Marina in less than half mile away, bring your kayaks or boat and have a truly memorable time, we have the space! Wake up to Trees, walking trails are less than a block away. This is the scene of one the great navel battles of the civil war, explore the history of the fort.. We are 30 mins from Historic downtown Savannah.

Guest favourite
A spacious living area features a brick fireplace as the focal point, surrounded by comfortable seating arrangements. Light wooden flooring complements the blue walls and a patterned area rug, while large windows allow natural light to wash over the room.
Home in Richmond Hill
4.8 out of 5 average rating, 209 reviews

Starfish Home for 10, Fast EV Charger+Pet Friendly

Surrounded by Spanish-moss-draped pines and close to recreation and historic sites, this home dates back to the early 1940s, when industrialist Henry Ford developed the Richmond Hill area. It lies about 35 minutes’ drive from downtown Savannah and just steps from the Myrtle Grove Plantation, where many movies and TV series have been filmed. Newly renovated, yet preserving the charm of yesteryear, guests will feel right at home as will well-behaved pets.

Guest favourite
A spacious studio is featured, with a large bed and a comfortable sofa facing a wooden coffee table. Natural light enters through multiple windows, and the indoor gas fireplace is visible next to a wall-mounted television. Soft tones create a relaxed atmosphere.
Flat in Wilmington Island
4.95 out of 5 average rating, 330 reviews

The Love Bird Suite

Located on the serene and historic Wilmington Island, this space was designed as a romantic couple’s getaway. Enjoy this spacious studio, equipped with a working indoor gas fireplace, a large soaking tub, floor to wall tiled shower, and an outdoor hot tub. Centrally located between Historic Savannah and Tybee Island, enjoy day trips to visit these amazing places and return to a relaxing and romantic retreat style stay.

Top guest favourite
A inviting living room features a spacious seating area with a light-colored sofa, an accent chair, and a coffee table. A large TV is mounted on a wooden console against the wall. Natural light filters through the window treatments, creating a bright, comfortable atmosphere.
Home in Savannah
4.93 out of 5 average rating, 112 reviews

Southside Sanctuary

This home-away-from-home offers a restful space and ideal retreat for families and friends. Nestled on a quiet street in a residential neighborhood near Lake Mayer, the house is bordered at the back by a greenway and small creek. Conveniently located close to the Truman Parkway, guests have easy and quick access to downtown Savannah, Tybee Island, and Skidaway. It is also close to several grocery stores and the mall.

Popular amenities for Ossabaw Island holiday rentals