Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Guest favorite

The welcoming front porch features a swing and two red doors, each adorned with a decorative wreath. Light fixtures hang from the ceiling, illuminating the space, which is framed by soft green siding and a concrete floor.

Home in Midtown

4.94 out of 5 average rating, 629 reviews

Upscale Duplex in Trendy Cooper-Young Area

Stay in a 100 year old house that has been professionally decorated for your comfort and enjoyment. Within walking distance of drinks, dining, night-life and recreation. Venture outside Cooper-Young with rental bikes and scooters. Or just pour yourself a glass of wine and enjoy the front porch swing or sit on the patio in the back yard. For those guests traveling with friends we offer a second unit in the same house. Perfect for couples wanting privacy but to share space for visiting.

Guest favorite

An outdoor deck features a mix of seating options, including a black metal table and chairs. A grill is positioned near the railing, with warm string lights installed above creating a welcoming ambiance. A large window provides views of the surrounding greenery.

Place to stay in Brighton

4.96 out of 5 average rating, 134 reviews

Gaga’s Getaway - Entire loft/bungalow

Gaga's Getaway is the ultimate place for a relaxing weekend. This cozy loft/bungalow is located in the town of Brighton, reminiscent of Mayberry from the beloved Andy Griffith Show. Although Gaga's Getaway is tucked away, city life is only 20 minutes away. In addition, this getaway is 30 minutes from Blue Oval City, 20 minutes from the naval base in Millington, and 45 minutes to downtown Memphis. Make sure to enjoy the southern hospitality and food you will encounter at the local eateries!

Top guest favorite

The exterior of a spacious brick home is featured, set against a lush green lawn. Large windows allow natural light to enhance the warm brick tones, while the surrounding trees provide a tranquil backdrop.

Home in Oakland

4.99 out of 5 average rating, 67 reviews

"The Bartholomew” 3 Bed 2 Bath King w/Jacuzzi Tub

Welcome to The Bartholomew—your perfect retreat! This spacious 3-bedroom home with a study offers comfort, tranquility, and modern amenities. Enjoy a fully equipped kitchen with a coffee station, a master suite with Jacuzzi, and a patio with a grill for relaxing evenings. With WiFi, laundry, and self check-in via keyless entry, your stay is effortless. Located in a peaceful neighborhood, unwind, recharge, and create unforgettable memories in this cozy, serene home. “Your Cozy Retreat”

Top guest favorite

The kitchen features wooden cabinetry and a large countertop with seating for two. Appliances include a black refrigerator and stove set against a backdrop of wood paneling. Soft lighting from overhead fixtures highlights the warm tones of the space.

Farm stay in Olive Branch

4.96 out of 5 average rating, 379 reviews

Horse Farm Hideaway

Industrial farmhouse style meets southern charm on an idyllic horse boarding family farm safely outside of Memphis. Perfect location both for sightseeing in Memphis or bypassing the city entirely. Take a walk among the horses to decompress. Full kitchen and a large bathroom. No exterior windows. Guests sleep well in our quiet and private space. Due to safety concerns, no children under 12. Locals or those without prior positive reviews will be rejected. Our property is smoke free.

Guest favorite

An efficiency apartment features a full bed and a futon, situated on a neutral-toned wood floor. A red couch with decorative cushions adds a pop of color. A coffee table is centered on a soft rug. Light filters in from an overhead fixture, illuminating the space.

Place to stay in Moscow

5 out of 5 average rating, 8 reviews

The Loft is a private apt w/ 1 bed & 1 full bath

Peaceful upstairs private efficiency or office space. A full bed and a futon bed. Garden, grills, parking & backyard are shared with downstairs owner/ occupants. Absolutely No Parties. Located next door to Moscow Police & City Hall. Note: No Smoking indoors & Leave no butts behind! 5 min from Jupiter Café, Pleasants Grocery, Local Eats & Boutiques! Ghost River / Wolf River access! 30 min from West Tennessee Skydiving! 43 min from MEM AIRPORT! **Low ceiling & very steep stairs**

Guest favorite

A cozy corner of the living room features a brown sofa adorned with decorative cushions. A small side table adds functionality. Natural light enters through the window, which is partially covered by blinds. A large mirrored frame reflects the inviting atmosphere.

Guest suite in Shelby County

4.85 out of 5 average rating, 382 reviews

Duplex attached to our house! Safe Memphis suburb!

Private outdoor entrance. There is no access from the main house to the duplex and vice versa. It’s completely private with no shared spaces. This cozy duplex has a living room with kitchenette, a bedroom and a bathroom and is attached to our house. (See picture of house in our listing.) Sleeps 2 adults, and up to 2 small children. We don’t accept guests from Memphis and don’t feel our property is right for romantic getaways considering we live next door and have kids and dogs.

Top guest favorite

A cozy living room area is showcased, featuring a dark sofa and a light-colored coffee table. Accent pillows add warmth to the seating options. A lamp and two candles create a soft glow, while a wall-mounted mirror enhances the space's depth.

Guesthouse in Cordova

4.91 out of 5 average rating, 241 reviews

BE OUR GUEST: Adorable Guest House in EastMemphis

Perfect for passing through Memphis. Located in a beautiful neighborhood near 140. Weather you’re touring Memphis for the weekend or in for rotations at work, we have your home away from home waiting for you. Those who love being out doors will enjoy the wooded yard with a sitting area around the fire-pit. There is also a Sofa-sleeper (queen bed) for additional guest. Very centrally located and near I-40 allowing you to be most anywhere you need to be in 20 minutes.

Guest favorite

An outdoor porch area features a wooden coffee table surrounded by four lounge chairs, inviting relaxation. The space is partially covered, offering unobstructed views of the surrounding landscape, including open fields and trees against a clear blue sky.

Home in Collierville

4.96 out of 5 average rating, 152 reviews

Collierville home - 2 bedrooms sleeps 7

Memphis Meadows is **NEW** Country Living at its finest with new appliances/furniture with blazing internet (100+ Mbps). Located in Collierville; 20 mins to Germantown/Bartlett, 40 mins to Graceland, and 45 mins to Beale Street. Incredible mountain biking within walking at Herb Parson's Lake state park. Private Jacuzzi J-465 hot-tub available for guests to use. Beautiful views from second floor residential living area including a full porch and third floor bedroom.

Top guest favorite

A modern kitchen is featured, with light-colored cabinetry and a spacious island at the center. Elegant pendant lights hang above, while stainless steel appliances and a coffee maker are visible. A window allows natural light to illuminate the area, complemented by decorative wall elements.

Home in Millington

4.99 out of 5 average rating, 113 reviews

The Cottage at Kerrville

A cozy 3 bedroom cottage in the historic community of Kerrville, Tennessee. Situated on 5 acres with plenty of room to roam. Newly renovated, fully furnished. Complete with kitchen, laundry room, and oversized shower with endless hot water. Beds are queen size with new memory foam mattresses and ceiling fans in each bedroom. Covered carport with well-lit exterior. Seven minutes from the Navel Air Station in Millington, and 25 minutes from Downtown Memphis.

Top guest favorite

An open-concept studio layout is showcased, featuring a spacious bed with a light quilt, a cozy couch adorned with patterned cushions, and a small wooden table. A kitchenette area with a microwave, coffee maker, and utensils is present, complemented by decorative plants.

Guest suite in Collierville

4.95 out of 5 average rating, 236 reviews

Collierville cottage on 3 acre farm

Sun and summer has arrived ☀️Come enjoy our family farm located on 3 acres in the peaceful countryside of Collierville. We welcome guests in separate cottage with private entrance and porch overlooking pool. Look no further for a nature lovers retreat only minutes from city life. No trains or busy street noises just birds singing and crickets chirping. Amazing restaurants and shopping minutes away when you’re ready to explore! The pool is open.

Top guest favorite

The exterior of a spacious log home is depicted, featuring a large wraparound porch supported by muted stone columns. The roof is gently sloped, and multiple windows elevate the design. Surrounding greenery offers a serene atmosphere, while a stone wall partially encloses the property.

Guest suite in Lakeland

4.95 out of 5 average rating, 222 reviews

Log Cabin with Covered Bridge

Our property isn't just a place to spend the night, its a destination. A place to relax. We have been blessed to call this beautiful farmstead home for over 30 years. Upon entering the property you will traverse along the winding drive, rolling hills, across the lake on the covered bridge, and up the hill to the log home. Be sure to look around for the many deer, geese, ducks, turkeys, and other wildlife that also call our farm home.

Guest favorite

The exterior of a green tiny house is highlighted, featuring a covered porch with a wooden railing. Two potted plants with yellow flowers are positioned near the entrance, which includes a doorbell and window. Natural surroundings provide a serene atmosphere.

Tiny home in Atoka

4.85 out of 5 average rating, 169 reviews

Cozy and Quiet

This cozy tiny house is located off hwy. 14 on the edge of Shelby County and Tipton County. This tiny home sleeps 2 in a queen bed and 1 on a futon. Downtown Memphis is 30 min away. Millington, Bartlett, Atoka, Stanton, Arlington, and Lakeland are 20 min away. This home is in the country surrounded by beautiful trees. There is a pond, old barn, a few barn cats and chickens roaming the property. The property is gated and very quiet.