Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite
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 Cooper Young
4.94 out of 5 average rating, 654 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.

Top Guest favourite
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, 149 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 favourite
Guesthouse in Somerville
5 out of 5 average rating, 12 reviews

Quiet Country Garage Apartment - Sleeps 2 Adults +

Small garage apartment on owner's property in quiet country setting. Sleeps 2 adults + 2 children on one queen bed and a futon (makes full-sized bed). Kitchenette: microwave, toaster oven, electric tea kettle w/ instant coffee pkgs, refrigerator. Pots/pans for cooking on outside grill top. WiFi; TV w/ local channels and ROKU. Enjoy sitting on outside deck. 7 mins. to Blue Oval Ford; 30 mins. west to Memphis Wolfchase; 20 mins. west to Arlington (TN); 45 mins. east to Jackson (TN)

Guest favourite
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, 396 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.

Top Guest favourite
A charming yellow house features a welcoming front porch adorned with seating and hanging plants, accompanied by a decorative birdbath. Lush greenery and vibrant flower beds surround the home, with a large tree offering shade overhead.
Apartment in Memphis
4.99 out of 5 average rating, 385 reviews

Whispering Oak Secret Hideaway

Whispering Oak was lovingly built in 1908 by the Mothershed family. It is adorned by a massive Oak tree that holds a swing. We have divided the house into two private apartments. Secret Hideaway is on the right. There are 3 spacious rooms. Living/dining with adjoining kitchenette, large bedroom with closet with en-suite luxurious bathroom with walk in shower. There a lovely front porch with swing that provides amazing sunset views and a beautiful backyard with large covered portico.

Top Guest favourite
Guest suite in Collierville
4.95 out of 5 average rating, 250 reviews

Collierville cottage on 3 acre farm

Christmas on the farm has arrived 🎁 Come enjoy our family farm located on 3 acres in the peaceful countryside of Collierville. We welcome guests in separate downstairs guest house 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 closed in the winter.

Top Guest favourite
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 Cordova
4.85 out of 5 average rating, 407 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. Private! No shared spaces, no hidden cleaning fees. This cozy duplex has a living room with kitchenette ( mini fridge, microwave) and a bathroom and is attached to our house. 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 favourite
A cozy living area is observed, featuring two sofas and a central coffee table atop a decorative rug. Light pours in through large windows, illuminating the pink-hued walls. Glass French doors lead to the bedroom, enhancing the open and inviting layout.
Home in East Midtown
4.99 out of 5 average rating, 225 reviews

Midtown Memphis - Cozy & Quiet Refuge

Enjoy your time in Memphis like a Midtown-local in half of an adorable Victorian duplex. It's a comfy & quiet place to rest and close to so much! Our home is in a safe, friendly, neighborhood in the heart of the city. Harbert House is situated within walking distance to shops and food in Cooper Young + Overton Square, 2 miles from the Memphis Zoo and Overton park, & 3 miles from downtown. Harbert House was built in 1912 and has historic charm.

Top Guest favourite
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, 236 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 favourite
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, 202 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 favourite
A spacious bedroom features a comfortable bed dressed in light linens, complemented by decorative pillows. Two bedside lamps provide soft lighting, while a large window allows natural light to enter. A dresser with multiple drawers and wall art adds to the room's inviting decor.
Home in Arlington
4.98 out of 5 average rating, 179 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.

Top Guest favourite
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, 260 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!

Popular amenities for Oakland holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Fayette County
  5. Oakland