Holiday rentals with a pool in Tupelo

Central Tupelo Guesthouse with Pool

Centrally located in one of Tupelo’s historic neighborhoods, just minutes away from local eateries, parks, shops, Cadence Bank Arena, Tupelo Regional Airport, and the birthplace of Elvis Presley. Our space is complete with a large kitchen area, queen size bed, a spacious walk-in shower, bidet, as well as TV in both the living space and the bedroom so you can relax your way. You also have first access to our pool during the warmer months. This stay was originally known as Duckingham Palace 🖤

Tupelo Manor 6 bed/ 5 bath

Unique, charming, stately. This home just off Tupelo's downtown is great for large groups staying for games, weddings, or reunions! First built in 1955, this home has been updated throughout with modern amenities & spacious living areas. Enjoy ample room for multiple couples, families, wedding parties, or work groups. *Pool rules/info below* 1 mile to from Main Street Tupelo Super convenient to Toyota Plant, Cadence Bank Arena, Tupelo Buffalo Park, & Natchez Trace Full Kitchen 6 BR 5 baths

The Whistle Stop

Spacious home built in the late 1800s with all the old style charm. This house is truly amazing. Original hardwood floors throughout. Extra tall ceilings in oversized rooms are truly elegant. Modern amenities make this a perfect combination of yesteryear and comforts of today. Minutes from Eastport lake and marina, only a few miles to Pickwick Lake and the Tn River. Conveniently located to restaurants and grocery. This very large home will not disappoint. Come see us at the Whistle Stop!

A Barndominium Farmstay Experience & Retreat

BARNDOMINIUM RETREAT-One of a kind private experience just 10 minutes to the Square & Campus. Our 2/2 converted Barn has a luxurious King en suite BR, 2nd Full BR, furnished kitchen, coffee/tea bar, a deep south facing back porch w/ fire pit & grill patio. Expansive glass end wall has view of meadow, mixed forest & deer. EXTRAS-Indoor/outdoor Saloon, movie & projector theater. Pool time is just across the driveway. A rare peaceful setting for Experiential Travelers for meaningful memories.

Bunkhouse Blues 15 mi to Square saltwater pool

Feel refreshed when you stay in this rustic gem situated approximately 15 miles from the Oxford square and the University of Mississippi campus in this beautiful natural setting on 15 acres. During the day enjoy lounging by the pool and at night roasting marshmallows by the fire. At days end, sleep comfortably surrounded by the carefully curated Blues themed art and decor. Unwind and immerse yourselves in nature with lots of bird watching, stargazing, and the sounds of frogs and crickets.

The Potting Shed-Farmstay Experience & Retreat

Quaint 2 Q BR Shed Home with hi-end bedding, 2nd full BR, tiled tub/shower w 2 sinks, comfy sitting room w elec fireplace, fully furnished open air kitchen. Veranda swing overlooks the forest & has a grassy, fenced yard for your canine family member(s). The POOL is available just across the driveway. Enjoy the cozy, rustic countryside lifestyle of this curated private space. Only 10 minutes to The Square or Campus but stay home to be enchanted, relax in place and make meaningful memories.

House on the hill

Bring the whole family to this great place with lots of room for fun. Spacious house overlooking fields and pastures. From Vaught-Hemingway Stadium, take Hwy 6 east to Hwy 7 (exit New Albany) to Hwy 30 east. Head to Etta post office (approximately 30 miles). Once you see Etta Post office, take a right (Hwy 355) go 3.5-4 miles and turn right on county road 31 (3rd house on right). House on the Hill!!! Great location to see Ole Miss❤️ Driver available upon request for additional fee!

Magnolia Serenity: 2BD/1BA w/ Gym, Pool, BBQ Grill

Welcome to all nurses and travelers! Discover a delightful 2-bedroom, 1-bath rental located in the enchanting city of Tupelo, Mississippi. Nestled right in the heart of the city, our residence serves as the ideal launchpad for immersing yourselves in the abundance of experiences Tupelo has in store for you. We invite you to create lasting memories as you explore the city's captivating history, indulge in its culinary delights, and embrace the genuine warmth of its community.

Beach house

Adorable tiny home behind the main house in the backyard; quiet neighborhood in the heart of Tupelo. One bedroom/loft, full bathroom with small kitchen. A Living room with tv. Sip coffee on the porch with breakfast table. Enjoy your evening by the fire pit or on the deck. Many dining and shopping options nearby or take a stroll downtown just 5 minutes away. See Elvis’ birthplace and museum 10 minutes away or enjoy a walk at the park! All within a 10 mile radius!

The Nest Egg, 3BR Home by Velvet Ditch Villas

Escape to The Nest Egg—nestled in the picturesque countryside of Oxford! This charming retreat blends slow rustic living with modern comforts, offering a peaceful break from city life. Visit the wander nature trails, or relax by the pool. Perfect for a tranquil weekend or a family adventure, The Nest Egg rejuvenates your spirit and connects you with nature. Come experience the serenity and charm of farm living at its finest at The Nest Egg!

Cozy Cottage

New guesthouse with Indoor pool and lots of amenities Centrally located to Oxford and Tupelo MS 35 minutes to Ole Miss Campus 75 minutes to Memphis Graceland 75 minutes to MIA Airport 25 miles to Tupelo Regional Airport 25 Minutes to Elvis Birthplace 3 minutes to Tallahatchie Trails 8 minutes to William Faulkner Birthplace/Museum 10 minutes from historic downtown New Albany

Thaxton Meadows

Bring the whole family to this great place with plenty of space to spread out. The house is 4225 square feet heated/cooled set on 7 acres 20 minutes to Ole Miss and all the amenities of Oxford. 15 minutes to New Albany or Pontotoc and 40 minutes to Tupelo. Seasonal pool is open June 1st-August 31. (Garage access is NOT included)