Holiday rentals with a pool in Lookout Mountain

Sunset Haven 4BR + Pool + Hot Tub + Fireplace

Nestled on historic Missionary Ridge (10 mins from downtown), this cozy home offers panoramic views of Lookout Mountain, downtown Chattanooga, and the Tennessee river. This spacious 4 bedroom home @ 3300sq ft holds stunning views from every room of the house. MAIN FLOOR: Master w/full bath + Screened in porch, Living + Dining + Kitchen (open layout), gas fireplace + half bath DOWNSTAIRS: Queen Suite, Queen Bedroom, Bunk room, Full Bath, Laundry Room OUTDOOR: Large deck, Pool, Hot Tub, Garden

Value · Location · Accuracy

~Pet Friendly~Riverfront Condo W/ Balcony

~Pet Friendly Condo~ Slumber soundly in a bedroom with Egyptian cotton sheets and room-darkening curtains. Start the day with a workout in the gym and a cooling dip in the pool, then head back for Keurig coffee and breakfast in the kitchen while viewing the 55" Roku TV. This condo comes with one designated free parking spot and extra guest spots that are first come first serve with additional paid parking on the street for extra vehicles, parking is free after 6pm Mon-Sat and free on Sundays.

Family · Value · Cleanliness

Riverwalk Retreat• Spacious• Pool • 5 min>Downtown

Centrally located near Chattanooga's most popular attractions, this newly decorated, Riverwalk Retreat has everything you’re looking for! -Community Pool -Neighborhood Riverwalk access (16 miles of paved trailhead along the Tennessee River) -5 minute drive to the Incline Railway, Ruby Falls and Southside Eateries -8 minute drive to the Aquarium -10 minute drive to Rock City Additionally, your retreat is conveniently located near local coffee shops, hiking, boutiques, breweries, and Publix!

Location · Value · Access

Family Fun - Private Pool, Spa & Mountain Views

Welcome to a beautifully designed lower-level guest suite. From the moment you step inside, you’ll notice that every detail has been thoughtfully curated with your comfort in mind. Unwind in the hot tub, splash in the pool, end the day making s'mores with the kids as the sun sets. This property is perfect for 2-4 guests, 5 with a baby. "Paradise. We could not have asked for more. The suite was beautiful and stocked with everything we needed... The pool and hot tub were so relaxing." - Heidi

Family · Location · Kitchen

Wooded Writer's Retreat with Pool

Book NOW for family pool fun get-away. A peaceful health-conscious 3-bedroom tri-level at the ft. of Lookout Mtn. 2 fireplaces. Upper 2 levels are yours exclusively. Lower level office not accessible. Advanced air purification system. Bottled water NOT needed with reverse osmosis filter. Ideal for families, small retreats, or parents of students. Covenant College is visible from the kitchen & attractions minutes away. Plan ahead for Spring-Summer. Open pool season. No pets allowed.

Family · Value · Sleep quality

Wildflower Cabin – Hot Tub & Mountain Views

Perched atop a scenic bluff in Bryant, AL, Grant Summit Cabins offers nine charming cabins overlooking Nickajack Lake. Each cabin features panoramic mountain and water views. With a variety of layouts and sleeping capacities, there’s something perfect for romantic getaways, family vacations, or group retreats. Whether you're sipping coffee on the porch or exploring the nearby hiking trails, relaxation comes easily here. Grant Summit Cabins blends comfort & nature for an unforgettable stay.

Family · Value · Decor

Quiet A-frame cabin w/pool ~ perfect for families!

This NEWLY RENOVATED, Modern A-frame Mountain Cabin is only 7 minutes from I-75 with beautiful views! 5 bedrooms, 3 bathrooms, and currently sleeps up to 12. The outdoor pool is perfect to relax by during the summer! Amenities Include: o Fully stocked kitchen with appliances o 9 beds o Over 2700 sq ft o Washer + Dryer o 6 decks with seating throughout and gorgeous views o Smart 65” TV o Pool Table o Outdoor Pool: Open May-Oct o Quiet area surrounded by nature

Family · Value · Kitchen

Modern Ridge-Top Sanctuary: All-Year Swim Spa

Escape to your private 12-acre contemporary sanctuary. Pinhoti is a beautiful modern getaway designed for total seclusion on 12 private acres. Built for up to 4 guests, this stylish retreat replaces traditional dark cabin logs with clean lines and large glass windows. As soon as you enter the front door, the floor-to-ceiling views pull your eyes straight through the lounge to a spectacular timber deck overlooking Taylor Ridge.

Location · Family · Check-in

I Fly Cabin: Watch Hang Gliders /Paragliders Soar!

Welcome! The cabin is located at the base of Lookout Mountain Flight Park. Watch hang gliders take off and land from the front windows or deck. Have fun!! ~maybe even take a tandem flight yourself! There is also no better place to hang wait! Hang waiting is when you wait until the conditions are right to fly hang gliders or paragliders. Once the weather is flyable, enjoy a front row seat to the south side tandem takeoffs!

Location · Family · Barbecue

Chatt Vistas Oasis-3bdrm-5m to TN-PoolDeckBBQFireP

Welcome to your charming country retreat! This fully furnished home offers a cozy and relaxing atmosphere with its inviting pool, fire-pit area, and a spacious, fully fenced backyard. Centrally located just 4-6 minutes from TN/St. Elmo and Lookout Mountain, it's perfect for exploring Chattanooga. The home features 3 bedrooms and 1 bathroom. Enjoy your peaceful getaway in this delightful and convenient destination!

Location · Family · Comfort

Big Time Hill Cabin with an indoor pool, hot tub,

Big Time Hill is located in Paradise Pointe, a gated mountain retreat at the tri-state corner of AL/TN/GA. Hike the trail to stand in three states at once! Enjoy access to the huge indoor pool house with a communal hot tub, two indoor slides, an outdoor deck, seating, and more. All 19 rentals share these amenities. Plus, enjoy two small basketball courts, sand volleyball, horseshoes, and more for endless fun!

Value · Location · Amenities

Lookout Mountain Retro Pad

Peaceful, mid-century bluff home with valley, city, and Blue Ridge Mountain views from the East Brow of Lookout Mountain! An outdoor fire pit, two indoor wood burning fireplaces, a bluff side pool, and outdoor seating to enjoy the beautiful views & singing birds. Open kitchen floor plan, natural light, and four bedrooms to comfortably accommodate up to 6 guests (up to 8 guests for immediate family).

Value · Family · Hiking