Family-friendly holiday rentals in Plainview

Edwardsville Apartment - The Woodland Suite

The apartment in the lower level of the home has recently been renovated, with a walk-out private entrance, a full kitchen & dining area, full bath, bedroom and a cozy living space. Situated just 35 minutes from downtown St Louis, in the safe and affluent community of Edwardsville, this property sits in a quiet cul de sac on a wooded lot right in the heart of the city. We are just a few minutes from the SIUE campus, Edwardsville HS, & I-270. Coffee/restaurants/shops/parks/trails just 2 min away.

Kitchen · Indoor spaces · Grill

🦌 Deer Hill a LR Country Estate Est. In 1938 🫶🏼

Once upon a time there was a home situated on the Perryville Hwy far far away from the hustle & bustle of big city living. 86 years later it's now a hidden gem in the middle of everything LR has to offer. Don't overpack, you'll find it loaded not only with flair & jaw dropping features but also stacked with amenities not found at most rentals. Making Deer Hill "the spot" for family & friend gatherings!! Welcome to Deer Hill our old family home, where you'll want to come back time and again!

Kitchen · Indoor spaces · Comfort

Farmhouse Retreat

Need a break from the busyness? Just driving through? Coming in to town to see family or friends? Want a weekend getaway? Come stay in a relaxing and well furnished farmhouse located on 40 acres in the hills of Arcadia, OK. The property features over a mile of wooded walking trails, a three acre pond, family friendly farm animals including everyone's favorite, Kenny the Clydesdale, a scenic back porch and more. The property and farmhouse is family friendly and accommodates up to six guests.

Family · Kitchen · Checkout

Smoky Mountain Lighthouse on Douglas Lake

The Lighthouse at Hunkerdown Hollow provides a waterfront experience at the base of the Smoky Mountains. This unique lodging brings you up close to the natural beauty of the Douglas lake resevoir. Home to over 200 species of bird, and recognized as a Bassmaster top 100 fishing lake, the Lighthouse puts you right in the middle of it all! While every window in the lighthouse has a water view, the top level boasts a 360 degree view of water & the treetops, to observe all the beauty of Douglas!

Indoor spaces · Kitchen · Walkability

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Kitchen · Family · Air conditioning

Storybook Cottage near Leipers Fork, TN

Storybook Cottage is just as you would imagine . . . charming and dreamy, the perfect place to get away from your fast-paced world to find the things that matter most. From the painted poplar wood floors and the cathedral ceiling to the sleeping loft, outdoor shower and stacked stone wall, this cottage is one of a kind and is perfect for a romantic getaway, small families, weekend with friends or as an artist / writers retreat. Storybook Cottage has been featured in several publications.

Indoor spaces · Family · Checkout

Lake Front w/ Pool! Between Ark & Creation Museum.

If you are looking to experience lake life, look no further! Our Guest House sits on the beautiful 140 acre Bullock Pen Lake. It's a great place to relax, or enjoy kayaking, paddle boating, paddle boarding and fishing. We have one of the best views of the lake. The Guest House is fully renovated and decorated with relaxation in mind. It has everything you would need for your stay. After all, the lake is where your worries fade and memories are made! (The pool is now OPEN!!!) 5/11/26

Family · Indoor spaces · Checkout

Quiet little farm stay in Austin - pet friendly

Welcome to our little old farmhouse. 🏡❤️ If you love being greeted by friendly, nosy sheep, then this is the place for you! Welcome to our little farm, where we love making our guests feel right at home. This is a place to slow down, relax, and unwind from the hustle and bustle of everyday life while enjoying a little taste of simple farm living. Come as a guest, relax like you’re at home, and leave with a few memories—and hopefully a little love for our farm family. 🐑🐐🐴✨ .

Kitchen · Indoor spaces · Access

Lost Valley View Cabin

Enjoy this cozy cabin nestled in the heart of the Ozarks. With a view of Lost Valley and beyond, the front porch is a nice place to relax and unwind! With a full kitchen, fire pit, horseshoe pit, charcoal grill, and more we wish you to be able to vacation deliberately, comfortably, and affordably! Please hit us up with any questions and thank you! We do have Pyrenees dogs who watch over the farm, they are harmless and just part of the landscape. Firewood for sale, 5$ an arm load!

Kitchen · Family · Access

The Hideaway

Welcome to your private hot tub & (Seasonal) above ground swimming pool!! ENJOY!! 👙 🌞 NO PARTIES Your family will be close to everything when you stay at this centrally-located cottage. Carthage, Webb City & Joplin. Enjoy our quiet, peaceful, cozy cottage, equipped with a queen size bed & full size Lazy Boy hideabed. Sit on the wrap around porch & watch the deer & turkey stroll thru. We are located about 1 mile off Route 66 and easy access to I-49 & I-44.

Indoor spaces · Family · Bathroom

River Cabin/UTV/Trails/Kayaks/HotTub/OutD Shower/

The James River Cabin is a luxurious secluded cabin nestled among the trees on 90 acres of river front property. It is just 10 short miles from Springfield, MO (Buc-ee’s and Bass Pro) less than an hour from Branson, MO. On-site activities are numerous and include bicycling, trail hiking, utv trail riding, kayaking, fishing, hot tubbing, and swimming in your own personal paradise. The river access is a short but fun two minute utv drive from the cabin.

Kitchen · Family · Layout

Luxury Lakeview Treehouse • Stunning Views • Lake

Welcome to Tree + House II at Indian Point! This modern, luxurious treehouse is designed to accommodate up to four guests and offers a serene retreat in a peaceful forest setting. Featuring stunning floor-to-ceiling windows, you’ll enjoy spectacular views of Table Rock Lake right from your cozy hideaway. Conveniently located just minutes from Table Rock Lake and Silver Dollar City, it’s the ideal destination for both relaxation and adventure.

Family · Kitchen · Decor