Holiday rentals with a kayak in Winston County

Lakefront Escape | Fish, Kayak & Relax

Discover Paradise Point, a luxury lakefront cabin on Smith Lake offering modern comfort & serene waterfront views. Enjoy panoramic lake scenery with direct access to a private dock for fishing, kayaking, & paddleboarding. Perfect for families, couples, & groups, this spacious retreat features a large deck, firepit & peaceful outdoor seating. Whether relaxing or exploring, Paradise Point delivers the ultimate Smith Lake getaway with adventure, comfort, and unforgettable natural beauty year-round.

Water's edge, gated community with pool, hot tub

No detail was spared in outfitting this space, all with breathtaking lake views from nearly every window. The double slip dock is steps away, complete with SUPs, kayaks, an inflatable lily pad, plus a lift for your boat! Perfectly located within a gated, private hamlet with access to the hilltop community pool and clubhouse. Dockside delivery with pontoon rentals, Level 2 EV charger. Come see why we were featured in Architectural Digest, Birmingham Home & Garden and The Lakeside Life magazines!

Emerald Bay on Smith Lake

Welcome to Emerald Bay - a luxury lake home named for its expansive bay views in clear year round water. This custom home completed in 2022 is situated off the main channel in a protected bay. You will find breathtaking views throughout the home and outdoor entertaining at its finest. Enjoy swimming and water sports right off the stunning rock shoreline or from the 2-story double slip dock with roof top entertainment space. The large fire pit and hot tub provide entertainment after dark.

NEW BUILD Redeemed Lakehouse

All new. Wheelchair accessible. Enjoy the convenience of stepping out the front door to the dock, zero steps and easy access where you can hang out or jump from the top dock or swim on the bottom deck. Conveniently located to Lakeshore Inn restaurant and Marina, Chef Troy Restaurant, Lakeshore Convenient Store for pizza, and Smoking Pig BBQ. Queen & twin first bedroom, queen second and two full in third while loft has four twins. WiFi and TV in every room. Enjoy the breathtaking views!

4BR/3Bath Lakefront Home | PrivateDock | Secluded

Cane Creek Hideaway is located on Lewis Smith Lake within the beautiful William Bankhead National Forest. Our lake home (Built & Established in 2023) is a secluded, private retreat with 130' of waterfront. We offer a private swim dock. There are 4 adult kayaks and 2 child kayaks provided for your use. The property itself is almost 2 acres. We offer a 4 bedroom, 3 bath home, which is the perfect getaway for a family or group of friends. Experience The Beauty of Lewis Smith Lake with Us!

Romantic Cave Hideaway & Waterfalls on Smith Lake

Discover a true wonder right on one of the most beautiful manmade lakes in the country. Your one-of-a-kind stay is a cabin nestled inside a real cave with all the comforts you need to fully enjoy lake life. Unwind to the sound of a private, natural waterfall, sip coffee or go fishing on the pier, and enjoy outdoor showers that heal the soul. Perfect for couples, adventurers, and anyone craving a retreat, this hidden gem will satisfy those looking for something truly unique.

Lakefront-Hot Tub-Outdoor Shower- Deep Water-Dock

Luxury lakefront retreat on Smith Lake with deep, year-round water and stunning sunset views. Fully remodeled 2BR with designer interiors and panoramic lake views. Private dock, kayaks, hot tub, outdoor shower for two, Solo firepit, and spacious deck for relaxing or entertaining. Ideal for romantic getaways, couples, or families. Concierge add-ons available; must be booked in advance. Proudly owner-managed for a more personal, responsive, and elevated guest experience.

Lake Acess! Views! Boat Dock! Hot Tub! Gameroom!

Escape to this brand-new luxury lakefront retreat on Lake Smith in a private gated community. This 5-bedroom, 3.5-bath home features soaring ceilings, a massive open floor plan, stone fireplace, fully stocked chef’s kitchen, game room with 8,000 arcade games, private gym, multiple lake-view decks, and a lake-view hot tub on an elevated platform. Enjoy your private dock with swings, kayak, and paddleboard. Designed for unforgettable lake memories with family and friends.

*The Copper Penny* at Smith Lake - 4BR/3BA

Kick back and relax as you enjoy this peaceful Smith Lake retreat located on Rock Creek. COMPLETELY renovated February 2021. Plenty of parking and multiple outdoor lounge/seating areas for you to enjoy. Swim platform with anchors for boat tie off, neighborhood boat launch, kayaks, stand-up paddle board, gas outdoor grill, fire pit with wood, cornhole set, Bluetooth speaker included. Non-refundable pet fee of $250. No more than 2 pets and breeds must be pre-approved.

Littleville on the Lake

Beautiful lake property in a secluded wooded area with five bedrooms all with a lake view, fire pit, entertainment area, two kitchens, two indoor fireplaces, outdoor patios with dining and grill, and a fun dock with paddle boards and kayaks for our guest. High Speed wireless Internet in the house and at the dock, makes both a great place to work or relax. Great woods to hike in or just enjoy the beautiful sunset from one of the screened in porches.

Smith Lake Glamping - ToNoMo Vintage Airstream

"TowNoMo" offers a unique lakeside retreat with a private screened in porch, and amenities that truly set it apart. Beyond the charm of a refurbished vintage Airstream, guests enjoy unparalleled access to Smith Lake's pristine waters. This property includes complimentary use of a private dock, kayaks, paddleboards, and fishing gear plus a first booked, first served complimentary boat slip — luxuries not often available elsewhere.

Sipsey Serenity at Lakeshore East on Smith Lake

This three-bedroom, 2.5-bath house in the Lakeshore East community on Smith Lake comfortably sleeps up to 12 guests with nine beds. Enjoy the large swim pier and a double boat dock on your waterfront, perfect for water adventures. Surrounded by nature, this beautiful retreat can be enjoyed year-round for relaxing, fishing, boating, or just unwinding in a peaceful setting. Come experience the best of the best on Smith Lake!