Holiday rentals in Oakland

Collierville cottage on 3 acre farm

Spring is starting to bloom 🌸 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 until late May. Water is freezing

Designer Skylight Serenity, Projector, Gated Prkng

Immerse yourself in the Soul of Memphis in our centrally-located 1907 Arts & Crafts Carriage house. This luxury tiny home was taken to the studs and completely redone with historic preservation and architectural design at the heartbeat of the project. Nestled in the Historic Annesdale Mansion Preservation District, we're the ideal space for a small family, a couple's getaway, or a traveling nurse. State-of-the-art home theater, 24' cathedral ceilings, gated parking under carport & full kitchen!

La Casita Memphis

-Private back house and backyard in the University of Memphis neighborhood -Secure driveway parking including inside backyard gate if preferred -Centrally located in sprawling Memphis. 12 minutes from the airport and less than 20 minutes from all of the main sites including Graceland and Beale. -Comfortable queen bed, coffee station, newly renovated bathroom. -Guests who live locally will not be accepted -Early check-in sometimes available upon request, $15 fee for 12:30 PM check-in time.

The Bartholomew: 3BR/2BA • King + 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”

Birch Cottage: midtown charm & driveway parking

Peaceful guest house with central heat and air, close to everything and no cleaning list! Enjoy driveway parking and complimentary snacks in our comfortable space full of vintage furniture and books. Our historic neighborhood is located blocks from the highway, 7 minutes from downtown, 5 minutes from midtown's best restaurants and shops, & 12 minutes from Graceland and the airport. Explore Memphis and rest in our charming cottage! A full size second bed is available by request.

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.

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

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.

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.

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.

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.

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!