Holiday rentals in Olmstead

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Top-rated holiday rentals in Olmstead

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Top guest favourite
Treehouse in Franklin
4.99 out of 5 average rating, 165 reviews

Treetop Views *Trails, Fishing *No Cleaning Fee

Amazing two-story house nestled high up in the trees. A true treehouse! This treehouse sits amongst a forest of poplar trees and feels very secluded and private. It has spectacular views of Kentucky’s rolling hills as it looks out across the valley. This treehouse was hand built and handcrafted with love and attention to detail. Located just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) and Mammoth Cave (55 min).

Top guest favourite
A tiny house is depicted, featuring a dark exterior with red accents around the windows and door. A wooden deck surrounds the entryway, complemented by a railing. Open countryside is visible in the background, with expansive fields and a clear blue sky.
Tiny home in Rockfield
4.97 out of 5 average rating, 101 reviews

Private, Tranquil Tiny Home With Countryside Veiws

Just 20 minutes from downtown Bowling Green and one hour from Mammoth Cave, Nolan Lake, Barren River Lake and other outdoor attractions. Our Tiny Home is a private, cozy, tranquil retreat nestled on 5 acres in the Rockfield, KY countryside. We hope you enjoy all the thoughtful elements we put into our tiny home! So read a book, play a board game, sit on the porch, or back deck and soak in the views while allowing yourself to relax, and unwind from the stresses of the world. License # WC00

Guest favourite
An aerial view of the property reveals a spacious deck surrounding a hot tub, nestled among lush greenery. The multi-level building showcases large windows, inviting natural light. A creek flows beside the structure, enhancing the natural setting.
Home in Springfield
4.91 out of 5 average rating, 233 reviews

Stunning Treehouse Mansion

Welcome to Kelly’s Jubilee. Breathtakingly beautiful home. A place to relax and enjoy a perfect retreat from the hustle and bustle of life. Once you’ve rested you can take around a 30-minute drive to Nashville and embrace some of America’s best entertainment. We have priced this place very low so that a couple can afford this as a romantic getaway. After the first two guests, we charge $35 per person. Please be accurate with your guest count. We want to continue to keep our prices low.

Top guest favourite
The exterior of a rustic cabin features a combination of log siding and a green metal roof. A spacious covered porch welcomes guests, with large columns supporting the overhang. Surrounding trees provide shade and natural beauty, enhancing the serene rural setting.
Cabin in Russellville
4.95 out of 5 average rating, 177 reviews

Cozy Cabin with Private Walking Trail

Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

Top guest favourite
The exterior of the house is showcased, featuring a red brick facade with a contrasting gray roof. Green bushes are neatly trimmed along the walkway, which leads to the entry. The lawn is well-maintained, and trees provide natural shading in the surrounding area.
Home in Franklin
4.96 out of 5 average rating, 161 reviews

Pet-Friendly Modern KY Retreat | Cozy 2BR Home

Enjoy this renovated 1940s retreat in Franklin, KY! Perfect for work trips, romantic getaways, or weekend escapes! Full kitchen, two bedrooms with queen beds, washer and dryer, and fast, reliable Wi-Fi. Pet-friendly and welcoming to all, it’s perfect for families, couples, or groups! Just minutes from I‑65, you can easily explore Nashville, Mammoth Cave, and local Amish markets. Have questions or interested in long-stay pricing? Click “Contact Host” before booking—we’re happy to help!

Guest favourite
The treehouse is illuminated by soft outdoor lights, highlighting its wooden structure and welcoming design. A gently curving walkway leads to the entrance, surrounded by tall trees and a glimpse of Lake Malone visible in the background.
Treehouse in Lewisburg
4.97 out of 5 average rating, 140 reviews

Treehouse with HOT TUB!(Lake Malone)

Prepare to be taken to new heights as you enjoy this beautiful, private treehouse located on Lake Malone. It features an absolutely stunning view of the lake through an 8x14 glass door that opens up to allow the cool lake breezes to waft your cares away as you relax in the recliner. It also features a hot tub, large deck, full kitchen, Jacuzzi tub, rainfall shower, beautiful woodwork, two complimentary kayaks, and many other unique features that will make your stay unforgettable.

Top guest favourite
A cozy cabin is nestled among lush greenery, partially obscured by mature trees. A gravel path leads to the entrance, which is flanked by wooden accents. A small outdoor seating area is visible, enhancing the connection to the serene natural surroundings.
Cabin in Chapmansboro
4.96 out of 5 average rating, 387 reviews

White Duck

Keep it simple at this peaceful and centrally-located cabin minutes from Interstate 24. Twenty minutes from Clarksville, APSU and nearby Fort Campbell KY to the north and thirty minutes from downtown Nashville and all it has to offer to the south. The quiet woodsy setting and comfortable interior of White Duck provide a restful transition from a day of sightseeing or an exciting football or hockey game. **There is a $50 pet fee** Please include your pet during the booking process.

Top guest favourite
An inviting open-plan living space features a rich leather armchair and a sleek wood stove. Large windows frame views of the surrounding forest, with a dining area visible in the background. Natural wood accents and warm tones create a cozy atmosphere.
Cabin in Goodlettsville
4.94 out of 5 average rating, 517 reviews

Enjoy Nature at a Secluded Cabin near Nashville #2018038413

Made from reclaimed materials, this charming and newly constructed cabin has a vintage style that sits perfectly amongst the forest. It features a gorgeous open plan space and floor-to-ceiling windows that provide a 180-degree view of nature outside. Secluded on its own quiet 42 acres, the cabin lets you feel alone with nature. Further out, there's easy access to stores and restaurants with a few lovely places for antique shopping. Nashville itself is just a short drive away.

Top guest favourite
A serene view of Lake Malone is captured from a wooden deck, adorned with autumn leaves. The calm water reflects the colorful foliage and the sky, contributing to a peaceful atmosphere. A hammock can be seen near the railing, inviting relaxation.
Home in Lewisburg
4.94 out of 5 average rating, 109 reviews

The FunKY Bean

Take it easy at this unique and tranquil getaway on beautiful Lake Malone. Relax in a hammock, swim off the dock , kayak , stand up paddle board, fish, or enjoy a beautiful sunrise while drinking your specialty coffee or tea! With the bean theme: There are oversized bean bags to relax on and a coffee station with LOTS of coffee options ( including Esspresso maker)! The funky bean is a real spot to get away from the hustle and bustle of everyday life and take it easy!

Top guest favourite
A charming treehouse is nestled among tall trees, featuring earthy wooden tones and a rustic design. Soft outdoor lighting creates a cozy ambiance, while a path made of stones leads to the entrance. The treehouse is elevated, providing a unique vantage point into the surrounding nature.
Treehouse in Greenbrier
4.98 out of 5 average rating, 304 reviews

Nashville Luxury Dream Treehouse +Spa

This beautifully designed and luxurious treehouse sits on a ridge overlooking our creek. With only a 25min drive to downtown Nashville, you are tucked away amidst the towering hardwoods---away from the city noise. With careful attention to detail, the treehouse decor and design is meticulously curated to create an atmosphere of rest and beauty. This space is ideal for a couple, but can sleep four (twin beds in the loft). Parties are not permitted on the premises.

Top guest favourite
The cottage is surrounded by lush greenery and tall trees, offering a serene and natural setting. A winding gravel path leads to the entrance, showcasing landscaping with various plants. Warm sunlight filters through the trees, enhancing the peaceful ambiance of the rural environment.
Cottage in Hendersonville
5 out of 5 average rating, 170 reviews

Cozy Cottage Wooded Retreat

Our cottage is cozy, private, and safe! It is fully equipped to make your stay as enjoyable and carefree as possible. We have WIFI, 2 TV's Roku on both TVs, a Bose Radio with CD's, a DVD player with movies. We have a Coffee Station with Keurig & pods, a Mr Coffee with a coffee grinder. Completely equipped Kitchen. Tub/shower combo. Lots of privacy on your own back deck. You may see deer and wild turkey . Gas Grill provided. plenty of parking. NO PETS ALLOWED.

Top guest favourite
Two painted horses trot across a grassy field as the sun sets in the background, casting warm hues of orange and pink in the sky. Lush trees border the scene, enhancing a sense of tranquility in the natural landscape.
Cabin in Russellville
4.99 out of 5 average rating, 176 reviews

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Come relax in our brand new Amish-made mini-HIDEAWAY! (Couples, friends, mother/daughter, business, or ME-time). We built our DREAM PLACE (with a brand new hot tub, GAS grill, and GAS firepit), and we are now sharing it with you! Located on 20 acres in the beautiful hills of Kentucky, you will be AMAZED at the sunsets and quietness. There are no near neighbors except the chirping birds and our horses to pet, watch, and feed. Come be refreshed!

Popular amenities for Olmstead holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Logan County
  5. Olmstead