Family-friendly holiday rentals in Tupelo

5 out of 5 average rating, 103 reviews

A charming farmhouse exterior features a red metal roof and a welcoming front porch with rocking chairs. Lush greenery surrounds the porch, with colorful plants and flower beds lining the walkway. Two dormer windows add character to the roofline.

Farm stay in Belmont

Farm Stay - Savannah's Sanctuary - Rock Creek Farm

Savannah's Sanctuary sits on a 600 acre farm located in NE corner of the state. You’ll be charmed by this simple 4th generation family owned farmhouse. Furnished with interesting old pieces of history like furniture, tools & books . Owners live nearby. >Tiffin Motor Homes (18 minutes) >Bay Springs Lake (13 minutes) >Tishomingo State Park (7 minutes) >Natchez Trace Parkway (12 minutes) >Shiloh National Military Park - TN >Elvis Presley birthplace - Tupelo, MS >Dismals Canyon - Phil Campbell, AL

4.99 out of 5 average rating, 175 reviews

A comfortable leather sofa adorned with decorative throw pillows is positioned near a wooden coffee table. A small mirror reflects warm light from two lamps, while a vase of fresh flowers adds a touch of nature. A compact desk is visible in the background.

Cottage in Blue Springs

Large Studio Cottage/Quiet & Peaceful WS

“Windsong” Spacious studio cottage. Everyone raves... "It feels like home." "It's so cozy." "I could live here." Keurig with K cups ready to enjoy. Lg oversized queen bed is just as comfy as it looks. FiberOptic internet with 43" smart TV with Roku Channel movies and live tv—a firepit for your enjoyment while surrounded by beautiful towering trees and a view of the lake. Roll away twin bed if requested… must request upon booking. 2 Cottages available...great for 2 families get away.

4.9 out of 5 average rating, 655 reviews

A living room features a dark blue couch adorned with decorative pillows, positioned near large windows dressed with light curtains. A coffee table sits centrally, displaying a stack of books and small plants. Wall sconces and a mirror add to the room's inviting ambiance.

Cottage in New Albany

The Cottage in Downtown New Albany, MS

Come and enjoy The Cottage in Downtown New Albany, MS! This newly renovated property boasts detailed interiors and modern luxuries, while still maintaining the cozy comforts of a weekend cottage. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

4.98 out of 5 average rating, 132 reviews

The exterior of a newly renovated home features a charming front porch supported by decorative columns. Large windows allow natural light to illuminate the space, while a well-maintained lawn and neatly arranged shrubs enhance the welcoming entryway.

Home in New Albany

The Queen on Cleveland

Come and enjoy The Queen on Cleveland in Downtown New Albany, MS! This new AirBNB is a sister property to “The Cottage”. This newly renovated home boasts detailed interiors and modern luxuries. Only a short stroll away from the vibrant shops and restaurants of Downtown New Albany, which was recently voted "Best Small Town in the Southeast" by USA Today. For bicycle enthusiasts looking to take advantage of the Tanglefoot Trail, please enjoy the convenience of our location!

4.86 out of 5 average rating, 148 reviews

The entryway features a door marked 'Beach House,' leading to a living area with a soft gray couch. A flat-screen TV is mounted on the wall, while natural light enters through a nearby window. Wood paneling adds warmth to the space.

Guesthouse in 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!

4.91 out of 5 average rating, 227 reviews

A cottage with dark blue siding is framed by neatly trimmed bushes and green grass. A covered porch features a bench alongside the main entrance, while tall trees provide shade in the background. A gravel driveway leads up to the home, adding to its inviting curb appeal.

Cottage in Tupelo

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 exterior of a historic home features a covered porch with American flag accents. Potted ferns hang from the ceiling, flanking two chairs and a small table. A stone walkway leads to the entrance, surrounded by landscaped greenery and blooming flowers.

4.97 out of 5 average rating, 398 reviews

Historic Charm Near Downtown Tupelo

Newly remodeled historic home less than a mile from Downtown Tupelo where you can enjoy shopping and plenty of tasty restaurants. The house has been thoughtfully furnished in a fun, midcentury modern style. The beds are very comfortable and the master bathroom has a giant shower and separate soaking tub to enjoy after a long day. Please note the house is close to the famous downtown train so you may hear the engine horn at night.

The cottage exterior displays a welcoming façade with light-colored siding and dark shutters. A manicured front lawn is visible, complemented by a clear pathway leading to the entrance. Large windows allow natural light to enter, while surrounding greenery enhances the serene atmosphere.

4.84 out of 5 average rating, 103 reviews

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.

The entrance features an inviting front door framed by two decorative planters. A covered porch provides shelter, highlighting the architectural details of the sloped roof and large windows that enhance natural light. Lush greenery surrounding the property adds to the welcoming ambiance.

4.97 out of 5 average rating, 106 reviews

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 exterior of a renovated house is displayed, featuring a welcoming front porch with wooden steps. Lush trees surround the property, enhancing the tranquil setting. A gravel pathway leads from the porch to the yard, where a patch of grass complements the natural surroundings.

4.98 out of 5 average rating, 444 reviews

The Tupelo Honey House Historic & Renovated - 2BR

Welcome to the Tupelo Honey Hous - stylish, cozy home in Tupelo—just minutes from downtown, I-22, and Elvis Presley’s Birthplace. Plenty of parking and a calm space to relax after exploring! ✨ Thoughtfully decorated with comfort in mind 🛋 Open living area for relaxing or working remotely ❄️ Climate-controlled for year-round comfort

4.96 out of 5 average rating, 230 reviews

An open-concept living and dining area is showcased, featuring a spacious seating area with a light-colored couch. A dining table with seating for multiple guests is positioned near the kitchen, which includes modern appliances. A flat-screen TV is mounted on the wall, complemented by warm lighting.

Farm stay in Tupelo

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!

4.99 out of 5 average rating, 521 reviews

A fenced entrance is framed by brick pillars and a wrought iron gate. Beyond the gate, a gravel pathway leads to a private outdoor area with seating, flowering plants, and a small fountain. Lush greenery surrounds the space, providing a sense of privacy.

Guesthouse in Tupelo

Cozy Guest House in Downtown Tupelo

Private cozy one bedroom with a bathroom guesthouse available. It is conveniently located in downtown Tupelo. Private entrance and includes wifi, roku tv, microwave, mini fridge, and Keurig coffee maker. Within walking distance to downtown Tupelo with great Restaurants.

Popular amenities for Tupelo family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Tiny home in Pontotoc County

The cottage is shown illuminated at night, surrounded by tall, bare trees. The structure features a front porch with a light fixture, highlighting the inviting entrance. A gravel path leads to the cottage, with gentle shadows cast by the moonlight.

5 out of 5 average rating, 27 reviews

Cypress - NEW Tiny Cottage @ Moon Lake Farm

4.84 out of 5 average rating, 124 reviews

A spacious lake house features a metal roof and large front porch, framed by lush greenery and manicured lawns. Rocking chairs are placed on the porch, inviting relaxation. Stone pathways lead to the entrance of the house, blending harmoniously with the natural surroundings.

Cabin in Tupelo

The Lakehouse at Colline Rouge (Red Hill)

The exterior of a charming bungalow is shown, featuring a light-colored facade and decorative shutters. Potted plants adorn the entrance, and two rustic chairs are positioned on the porch, inviting relaxation. Lush trees surround the property, contributing to a welcoming atmosphere.

5 out of 5 average rating, 36 reviews

Hollywood Bungalow

Tiny home in Pontotoc County

An outdoor gathering area is depicted, featuring a wooden structure with a roof, surrounded by a gravel pathway. Multiple gray Adirondack chairs are arranged in a circle on the lawn, offering a space for relaxation among the tall, green trees in the background.

4.95 out of 5 average rating, 39 reviews

Cedar - NEW Tiny Cottage @ Moon Lake Farm

4.89 out of 5 average rating, 53 reviews

The cabin exterior is surrounded by forest, with a large wrap-around porch featuring multiple seating areas. The roof is metal and slopes gently, while an American flag hangs from the porch. A gravel pathway leads to the entrance, enhancing the cabin's secluded feel.

Cabin in Dennis

Bay Springs/Tishomingo Cabin

4.6 out of 5 average rating, 15 reviews

A wooden deck curves gracefully over a serene body of water, reflecting clear blue skies. Bare trees line the opposite shore, contributing to a sense of tranquility. The sun casts gentle shadows across the deck, inviting relaxation.

Guesthouse in Myrtle

An Exciting Escape

A cozy bedroom features a spacious bed with a soft, textured blanket layered on top. Stylish pillows adorn the bed, while a comfortable chair sits nearby. Decorative wall accents in neutral tones add warmth, complemented by natural light filtering through the window with soft curtains.

Apartment in Tupelo

BudgetFriendly N’HeartOf Tupelo-6minsNMMC Hospital

4.97 out of 5 average rating, 99 reviews

A comfortable seating area features a brown sofa facing a rustic wooden coffee table, placed on a patterned area rug. The walls are accented with warm wood panels and metallic trim. A TV is mounted on the wall, and curtains frame the window.

Cabin in Ripley

The Outskirts

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 122 reviews

The exterior of a charming blue cottage is showcased, featuring white trim and a welcoming front porch with a railing. Lush landscaping surrounds the entrance, and the home is situated on a corner lot, with trees visible in the background under a cloudy sky.

Cottage in Tupelo

Cozy Chestnut Cottage- Downtown favorite!

A welcoming front porch features a classic bench positioned against a white brick facade. Lush greenery is lined along the pathway, interspersed with decorative stones and solar lights. Flower pots add a touch of color, enhancing the inviting atmosphere of the entrance.

5 out of 5 average rating, 113 reviews

The Heights - Town & Country Living

4.9 out of 5 average rating, 190 reviews

A rustic treehouse is illuminated by warm lights, nestled among tall trees. A well-defined gravel pathway leads to the entrance, bordered by greenery. The surrounding area features a cozy outdoor seating arrangement under an umbrella, enhancing the natural setting.

Treehouse in Tishomingo

Fern Hollow Treehouse Escape, cozy romantic!

4.97 out of 5 average rating, 139 reviews

A comfortable living room is presented, featuring two sofas positioned around a central area rug. A mantle with decorative items frames a wall-mounted television displaying a cozy fireplace scene. Natural light filters through windows covered by dark blinds, enhancing the inviting space.

Home in Pontotoc County

Farm house near I22

4.56 out of 5 average rating, 27 reviews

A spacious room features a large bed with a green quilt and decorative pillows. A comfortable armchair is positioned by the window, which is framed by orange curtains. A small dresser and a TV are also visible, enhancing the cozy ambiance of the space.

Apartment in Tupelo

Gated Condo in Tupelo

A living area features a dark sectional couch adorned with colorful patterned cushions. A round table made of wood sits in front, accompanied by a decorative stool. Bright artwork is displayed on the orange wall, and a tall, multicolored light adds a modern touch near the window.

4.77 out of 5 average rating, 35 reviews

Heart Break OG Bungalow - Downtown

The front exterior of a charming single-story home is highlighted, featuring a light gray siding and a welcoming navy blue door. A neatly trimmed lawn with shrubs and a path leads to the entrance, while an American flag adds a touch of character.

4.98 out of 5 average rating, 178 reviews

Spacious, historic downtown bungalow. Sleeps 10!

4.98 out of 5 average rating, 143 reviews

A pathway of stone steps leads from the lush green lawn to the entrance of the rustic carriage house. A wooden swing hangs nearby, providing a place to relax. The exterior features a combination of brick and wood, surrounded by trees.

Cottage in Amory

The Nook (on the Tenn-Tom)

Family-friendly home rentals with a pool

A cozy seating area features a gray sofa and a textured armchair, accompanied by a small side table. Natural light enters through large windows with rolled shades, illuminating the colorful area rug and potted plants positioned nearby.

Guesthouse in New Albany

5 out of 5 average rating, 4 reviews

Cozy Cottage

4.92 out of 5 average rating, 265 reviews

The exterior of the carriage house apartment is surrounded by manicured greenery and flowering shrubs. A shaded porch supported by wooden beams invites relaxation. A lawn extends in front, complementing the natural landscape of the property.

Apartment in New Albany

A Carriage Apartment at Possumhaw

4.85 out of 5 average rating, 13 reviews

The exterior of the house features a spacious front porch with a central entrance framed by large windows and stylish shutters. A manicured lawn extends toward the horizon, complemented by decorative shrubs on both sides. The structure is accentuated by a gabled roof under a blue sky.

Home in Thaxton

Thaxton Meadows

4.93 out of 5 average rating, 98 reviews

A modern living area is highlighted by a comfortable gray sofa and a round wooden coffee table. A kitchenette with essential appliances is visible in the background, along with a decorative Elvis Presley poster on the wall, adding a touch of local history.

Guesthouse in Tupelo

Central Tupelo Guesthouse with Pool

5 out of 5 average rating, 15 reviews

Home in Union County

House on the hill

The exterior of a spacious, stately home is showcased, featuring a classic white façade framed by large trees. A paved path leads to the entrance, where multiple windows allow natural light to illuminate the interior. The surrounding landscape displays a blend of grass and dirt pathways.

4.78 out of 5 average rating, 32 reviews

Tupelo Manor 6 bed/ 5 bath

A cozy living area is furnished with a dark gray sofa and matching loveseat, complemented by a wooden coffee table atop a plush black rug. Two lamps provide soft lighting, and a large window allows natural light to fill the space.

Apartment in Tupelo

4.9 out of 5 average rating, 10 reviews

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