Holiday rentals with outdoor seating in Lee County

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 🖤

The Lakehouse at Colline Rouge (Red Hill)

Lake house Living with this spacious 4 Bedroom 2 Bath Location right on the edge of Tupelo,MS. Enjoy watching Deer and Turkey from the Back porch with Fireplace Both Inside and Out with Beautiful View of the 16 Acre Lake. Roomy Kitchen, Great for Family outings or Couples Gettaway. There are King size beds in 2 Bedrooms and a Queen Sized in the 3rd. In the 4th BR there are 2 Separate Bunks Beds.....(Full on bottom, twin on top with easy access steps, the 2nd bunk has a Full & Twin.

Spacious, historic downtown bungalow. Sleeps 10!

The whole group will enjoy this central location in Tupelo! Walk to downtown Tupelo or take a quick drive to Elvis' birthplace. Family park across the street or enjoy your own large yard. Each room has T.V.'s and a huge closets. Master bath has jetted tub. Large kitchen is stocked with all the essentials. This property is pet friendly for 1 dog ($20/night). Please contact me for additional pets. The home sleeps up to 8 adults and 2 children. Bunks are for kids only due to weight.

The Heights - Town & Country Living

Welcome to The Heights! For Starters, you will be greeted with a fresh pan of Talbot Cinnamon Rolls.* For stays three nights and longer, you will also find a cheese, meat, cracker platter in the fridge. The kitchen is equipped with a Keurig coffee maker(drip and K-Cup) with coffee! The fridge is stocked with water, juice and sparkling water. This 70's era home has been immaculately cared for and has the comfort of 3 Bedrooms, two bathrooms, Living Room, and a complete kitchen.

The Sugar Shack Cottage

The Sugar Shack Cottage, with Hot Tub, King Bed New home Located in Historic Mill Town and near the famous rail tracks of Tupelo, step right on in and open the plantation shutters to a light and bright brand- new bungalow cottage filled with mid -century modern, bohemian and 70’s Hippy vibes. You will find a record player with some 70s and other good music, a few lava lamps, a salt rock lamp, and lots of conversation pieces. We are close to everything in downtown Tupelo.

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!

Cozy Dog-Friendly Cottage Near Downtown Tupelo

Settle into comfort at this cozy, dog-friendly cottage near Downtown Tupelo and Elvis’ Birthplace. With fast WiFi, same-day check-in, and a peaceful neighborhood, it’s ideal for remote workers, family visits, and travelers headed to the coast. Enjoy reliable Superhost care, safe parking, and home-style amenities close to restaurants, shops, and Tupelo’s top attractions—a welcoming space designed for easy living and stress-free stays.

The Callaway Cottage

Charming Cottage in Tupelo's Premier Neighborhood! Relax and unwind at this beautiful cottage featuring an amazing backyard in one of Tupelo's most desirable areas. Enjoy the convenience of restaurants just a 5-minute drive away, and take advantage of the large park across the street with tennis courts, pickleball, and a splash pad (available during summer months). Perfect for families or individuals seeking a tranquil retreat.

Unwind at Swallow Lane

Unwind and enjoy easy access to everything from this centrally located home, here in Tupelo, Ms. It’s super spacious and chic, whether you’re cooking in the kitchen, relaxing in the living room, or enjoying the closed-in patio. It has a outdoor bar area, as well as a fenced in yard. We have card/ board games, cornhole boards, and a fools ball table. There's enough fun for the adults and the kids.

The Apiary

Our private homestead is the perfect setting for your getaway. You’ll have the best of both worlds—with 20 acres of privacy with all the excitement of Tupelo just miles away. While here, you can relax in the serene outdoors while watching our farm animals graze. You can also gather eggs and enjoy them for breakfast!

HeartBreak All Shook Up Bungalow - Downtown

Step right into the All Shook Up Bungalow, nestled in the heart of Historic Mill Village! Born in 1910, this quirky charmer brims with personality. Original beadboard and a clawfoot tub scream vintage vibes, while each room bursts with color and rock 'n' roll flair.

The Sugar Magnolia *no cleaning fee $99 a night

Welcome to the Sugar Magnolia! Our guest house is centrally located with everything you need for a peaceful and comfortable stay. If you appreciate vintage charm mixed in with a little local art and a lot of southern hospitality, you’ll love it here!