Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite
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
4.97 out of 5 average rating, 72 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 favourite
Guest suite in Collierville
4.95 out of 5 average rating, 244 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.

Guest favourite
A neatly arranged bedroom is presented with a spacious bed adorned with a yellow throw blanket. A lamp casts a warm glow, while a wooden desk and chair with a minimalist design are positioned nearby. Bright light filters through a window dressed with simple curtains.
Guest suite in Idlewild
4.94 out of 5 average rating, 592 reviews

Cozy Friendliest Neighborhood in Heart of Midtown

Welcome to Midtown—the best place to be in Memphis! From here, you'll have easy access to everything — 0.5 miles to Cooper Young, 0.5 miles to Overton Square, 0.9 miles to Overton Park, 2.7 miles to Medical District, 3 miles to Beale Street. With its own separate entrance, designated parking in driveway, spacious bedroom, newly renovated bathroom, living room, kitchenette, washer and dryer, and sunroom with wrap-around windows, this upstairs suite has everything you need and more!

Top Guest favourite
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
4.92 out of 5 average rating, 264 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.

Top Guest favourite
The tiny house features a rustic wooden exterior with a red metal roof. Soft ambient lights are strung around the door area, which is framed by greenery and flower beds. Outdoor seating is provided by two white chairs on a gravel patio, creating a welcoming space.
Tiny home in Olive Branch
4.98 out of 5 average rating, 130 reviews

The Pony

-Boasting a small hoofprint of 128 square feet with a loft. Ideally situated in a safe area for those visiting/passing through Memphis. -Tranquil views of open fields, horses, and a variety of other furry friends at a working horse boarding barn. -Stay solo or with someone you don't mind cozying up to. Ideal for mobile guests comfortable with stairs and tighter spaces. Locals or those without positive reviews will be rejected. Our property is non smoking.

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, 399 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

Superhost
Apartment in Midtown
4.79 out of 5 average rating, 431 reviews

Vibrant Retreat | Near Beale & Overton Park

Experience the charm of this 1912 gem, blending timeless vintage style with modern comforts. Ideal for work stays or a cozy getaway, just steps from Memphis' top dining spots. ✔ High-Speed WiFi ✔ Smart TV ✔ Dedicated workspace ✔ Coffee maker + coffee ✔ Shared patio (2nd floor) ✔ Shared laundry in the basement ✔ Perfect for LONGER stays ✔ Within walking distance from restaurants Stay, unwind, and feel right at home in this timeless space.

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, 233 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, 186 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.

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, 171 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, 253 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!

Guest favourite
The tranquil lake reflects vibrant hues of orange and pink from the sunset, surrounded by trees with orange and gold leaves. The calm water mirrors the tree silhouettes and the fading daylight, creating a serene atmosphere in this lakeside setting.
Cabin in Oakland
4.98 out of 5 average rating, 202 reviews

TinyLakeEscape,Hot Tub near Memphis

Welcome to our 240 sq ft lakeside tiny cabin with hot tub nestled by a 10 acre lake. Try fishing from the bank or unwinding in the hot tub beneath the starlit sky. Whether it's the thrill of reeling in your catch or the quiet joy of stargazing, each moment is a chapter in your lakeside story. Escape to this cozy paradise where nature's beauty meets comfort.

Popular amenities for Oakland holiday rentals

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