Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Guest favorite

A compact bathroom space features a white toilet against a backdrop of rustic wooden walls. Decorated with a vibrant collage of food-themed art, the area is complemented by a red bucket containing toiletries.

Place to stay in Brighton

4.95 out of 5 average rating, 130 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

Home in Oakland

4.98 out of 5 average rating, 64 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”

Guest favorite

A suburban home is depicted with a well-maintained driveway leading up to it. Lush green grass surrounds the property, which features a mix of prominent shrubbery and flowering plants. The house displays a traditional architectural style with various rooflines and multiple windows reflecting the sunlight.

Guest suite in Cordova

4.85 out of 5 average rating, 367 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 modern open-concept living space features a wooden staircase leading to the upper level. A sleek kitchen island with bar seating is visible, complemented by large windows that allow natural light to fill the area. Warm wood tones create a welcoming ambiance.

Home in Collierville

4.98 out of 5 average rating, 143 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.

Guest favorite

Home in Crawfordsville

4.94 out of 5 average rating, 177 reviews

Sunset Ittelegna

Take it easy at this unique and tranquil getaway. Secluded, country home with lush gardens and saltwater pool. Sunset Ittelegna is just 20 minutes from Memphis, TN. Fully functioning mini kitchen and separate living space. There is a private drive dedicated to the freestanding home.You’ll enjoy sweeping views of the Delta and most breathtaking sunsets through a wall of floor to ceiling windows.Sunset Ittelegna offers privacy and comfort. Perfect for your getaway.

Guest favorite

An outdoor area is shown, featuring two adirondack chairs positioned near a fire pit. A barbecue grill sits nearby on gravel, while green grass and a wooden fence create a serene backdrop of a spacious lawn with trees in the distance.

Home in Holly Springs

4.84 out of 5 average rating, 196 reviews

Gallop-Inn Bungalow

PETS are welcome but please no more than 2 pets. Super easy self check in with keypad. Great location just outside the city and just a short drive to Historic Downtown Collierville, TN or how about a 30 minute drive to Downtown Memphis/Beale Street, Tunica Casinos, and Graceland. Plenty of Acreage for your pets to exercise. Enjoy the local sights of the area like Pickwick Lake and State Park less than an hour drive. Enjoy all the conveniences of home.

Top guest favorite

A spacious kitchen features a large island with a stone countertop, complemented by a stainless steel dishwasher. The area is illuminated by a decorative chandelier, with wooden ceilings and light cabinetry creating a warm ambiance. Plants and dining space are visible in the background.

Home in Somerville

4.95 out of 5 average rating, 21 reviews

Loosahatchie Lodge

Get out of the city and enjoy country chic living in this 4 bedroom, 4.5 bathroom farm house. Nestled on 3 acres and close to the Loosahatchie River, this beautiful sanctuary offers peaceful surroundings of farm, forest and star gazing. This area is teeming with wildlife including turkey, deer, and the occasional bald eagle. Allow the kids to enjoy nature, and make smore's, while you unwind with a glass of wine. Reset and reboot surrounded by nature.

Top guest favorite

An outdoor dining area is set with a rectangular table surrounded by six white wicker chairs. A small vase of flowers is placed at the center of the table. A pink umbrella provides shade, and a grassy area extends into the background, framed by trees.

Guest suite in Collierville

4.95 out of 5 average rating, 229 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

A log home surrounded by an abundance of autumn leaves creates a rustic setting. The spacious porch wraps around the house, providing seating areas with comfortable chairs. Large windows allow for ample natural light, and the facade features a prominent chimney that enhances the home’s character.

Guest suite in Lakeland

4.95 out of 5 average rating, 213 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 the tiny house is shown, featuring a green facade with a metal roof. A wooden deck with a railing enhances the entrance, accompanied by two potted plants. An outdoor grill is visible on the deck, providing additional amenities.

Tiny home in Atoka

4.85 out of 5 average rating, 158 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.

Top guest favorite

A modern kitchen showcases blue cabinets and a central island with a circular sink. Stainless steel appliances are positioned along one wall, while patterned tile flooring extends throughout the space. Natural light is let in through a skylight above, adding brightness to the area.

Home in Arlington

4.98 out of 5 average rating, 163 reviews

Arlington/65” HDTV/25 min to BLUE OVAL/garage

Enjoy a stylish experience at this conveniently-located zero-lot home in Arlington on the edge of Memphis right off of interstates I-40 and 385 (exit 25). Plenty of room for the entire family in this 1,900 sq ft home with king bed in primary, queen in room down, queen in loft, and queen in 4th bedroom. Large table to dine around, 65” TV in den, additional smart TVs in all bedrooms. Fiber high speed internet. 2 car garage.

Guest favorite

The front exterior of the cottage is depicted, showcasing a modern design with white vertical siding and a contrasting dark roof. A welcoming entrance is framed by a wooden overhang, with two symmetrical windows on either side. A garden bed with colorful flowers is visible near the pathway.

Guesthouse in Cordova

4.95 out of 5 average rating, 228 reviews

Cozy Cottage 1-BR Private Screened Porch

This one bedroom private cottage is tucked back in a little oasis we created for our family and guests. While enjoying morning coffee you will find space that insists you relax on the large screened-in porch and watch deer and other wildlife travel through the yard. Whether you are here to relax or work, there is no place better to do so than at your own oasis. We'd love for you to be our guest!

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Popular amenities for Oakland vacation rentals

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Other great vacation rentals in Oakland

A single-story brick house is depicted, featuring a neatly landscaped front yard. The driveway leads to a two-car garage with a white door. Windows with decorative shutters flank the front entrance, which is framed by a small porch. Lush greenery is visible in the background.

Home in Memphis

4.64 out of 5 average rating, 39 reviews

A NICE House in a Very SAFE Neighborhood!!

NorbertoRating, 5 stars1 week ago

We stayed here with our family and had a great time. The place was very clean, safe, and exactly as described. The neighborhood was quiet and felt very secure. Our kids loved the trampoline it was one of their favorite parts! The space was comfortable for all of us, and we had everything we needed. The host was kind and responsive. We would definitely stay here again.

A well-organized kitchen features modern appliances, including a stove and refrigerator. White cabinetry is complemented by a textured countertop. Natural light enters through a window with a sheer curtain. A dining island with round stools offers additional seating, and warm light fixtures provide illumination.

Home in Millington

4.88 out of 5 average rating, 8 reviews

The Urban Escape

CyeRating, 5 stars1 week ago

Jason was very attentive and “Johnny on the spot” when we needed assistance. He communicated very well and was available at a moments notice. The place was clean and had all the amenities one could need. Nicely decorated and good furniture. Highly recommend.

Top guest favorite

An outdoor kitchen area is showcased with a granite countertop and stainless steel appliances against a backdrop of corrugated metal. Natural light filters through the open structure, illuminating the space. A grassy area is visible beyond the kitchen, enhancing the outdoor experience.

Guesthouse in Covington

5 out of 5 average rating, 51 reviews

Peaceful, Private Studio 1Bath

AmyRating, 5 stars2 months ago

We love staying at Julie's studio, it is so cozy and always spotless! The bed is extremely comfortable, and there is plenty of space. It is a very peaceful and relaxing spot.

Guest favorite

The bathroom features a combination tub and shower, equipped with a decorative shower curtain. A toilet is positioned nearby, and a shelving unit displays neatly arranged towels. Soft lighting illuminates the space, and tiles create a clean, modern aesthetic.

Home in Brighton

5 out of 5 average rating, 6 reviews

Shady Oak Haven

CourtneyRating, 5 stars2 weeks ago

This is a cute, newly renovated home! Very peaceful and very spacious for our families. Would definitely recommend and most certainly stay here again when we are back in the area. Hosts were very quick to respond!

A cozy bedroom is highlighted by a king-size bed adorned with crisp white linens. A warm-toned lamp sits beside the bed, and a comfortable chair is positioned at a wooden desk. Natural light filters through the sheer curtains, creating a serene atmosphere.

Apartment in Memphis

4.86 out of 5 average rating, 14 reviews

Hot Pick! 1BR Suite w/ Free Breakfast, Pool&Gym

HannahRating, 5 stars1 week ago

I initially didn’t realize the apartment for rent was a hotel room, but was pleasantly surprised at how easy and great the location was to find/check into and stay! Trey was so thoughtful and responsive with all communication, it was nice to have such a personable experience for a hotel stay.

Top guest favorite

A covered porch area is shown, featuring two wooden rocking chairs with orange cushions, positioned on a patterned area rug. A pendant light hangs from the wooden ceiling, and swings are also visible nearby. Lush greenery and a gravel path extend into the distance.

Farm stay in Byhalia

5 out of 5 average rating, 34 reviews

Bobwhite's Retreat

DeanaRating, 5 stars1 month ago

Steven and Lindsay's home is perfect for a nice getaway from all the hustle and bustle. It was so comforting to sit in the rocking chairs out front and just listen to the birds chirp. I would stay again when we come back out.

A modern coffee maker is displayed on a kitchen counter, equipped with a glass carafe and digital timer. A blender is situated alongside it. A box of coffee sits nearby, providing ease for morning routines.

Condo in Cordova

5 out of 5 average rating, 3 reviews

1 Bedroom Condo

FrankRating, 5 stars1 month ago

Really enjoyed everything about the space would definitely stay here again.

Guest favorite

A covered porch area is displayed, featuring two light-colored rocking chairs positioned on a decorative area rug. Sunlight filters through trees, illuminating a small table with a potted plant nearby. A grassy yard is visible in the background, creating a serene outdoor space.

Place to stay in Moscow

5 out of 5 average rating, 7 reviews

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

KurtRating, 5 stars1 month ago

Was traveling through the south to accompany my son on his 8th grade trip and needed to stay somewhere comfortable and with fast internet and this was the perfect spot. Great use of space in a little loft where it’s cozy but it doesn’t feel small. Steps going up are pretty steep, so make sure you’re good with stairs, but was a great place to stay!

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Vacation rentals in Oakland

Top-rated vacation rentals in Oakland

Vacation rentals for every style

Popular amenities for Oakland vacation rentals

Other great vacation rentals in Oakland

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