Vacation rentals with a kayak in Montgomery County

Vacation home in Montgomery

A private pool is visible with a gently sloping lounge chair floating on the water's surface. Surrounding palm trees and natural stone formations create a serene ambiance under bright blue skies.

4.95 out of 5 average rating, 195 reviews

Prancing Horse Estates:10 acre resort w/pool, spa

Welcome to Prancing Horse Estates! This is a private gated 10 acre estate with private pool, spa and waterfall + 4 bedroom home. You’ll love it if you like upscale indoor style combined with beautiful outdoor space. 10 acres- 4 meadow and 6 densely wooded with 2 paths along the creek, with lovely poolside space with seating for 16+. Well stocked library, children’s room, indoor/outdoor games. Certified Wildlife Habitat® site with the National Wildlife Federation and Texas Conservation Alliance.

LocationOutdoor spacesCleanliness

A wooden dock stretches into a calm cove, bordered by lush greenery and trees. Boat lifts are visible along the water's edge, with several boats moored nearby. The serene landscape invites relaxation and outdoor activities.

4.84 out of 5 average rating, 116 reviews

LakeFront, Kayaks,Grill, Boat Dock, Deck, Netflix

Lake & Deck living at its BEST! 108ft of waterfront living. Enjoy quiet conversation as the sun sets. Fire up the grill and settle down to an al fresco dinner under the stars, float in the lazy cove, bring your boat and jet ski(s) or bring the gathering in to the fully equipped kitchen, long serving buffet, real wood fireplace and large dining room. Plenty of room for the kids to head up the spiral staircase and hang out. Walden Golf Club just down the street w/some of the best golf in Houston.

Outdoor spacesLocationBathroom

A spacious lakefront property is showcased, featuring multiple levels of outdoor patios and a large dock with boat and jet ski slips. The exterior is surrounded by lush greenery, creating a serene atmosphere. Soft evening light casts a warm glow on the structure.

4.94 out of 5 average rating, 49 reviews

Lake Conroe Oasis

Escape to this Lake Conroe lakefront gem! This 4-bed, 2.5-bath retreat features a boat slip, 2 jet ski slips, and a spa to relax after a day on lake. Enjoy multilevel patios with TV's, gas grill, and 2 fire pits for serene evenings. Open floor plan making entertaining a breeze. TVs in all bedrooms, washer/dryer, game area with a poker table and family games. In a secluded no-wake cove, it’s ideal for lake fun. Outdoor storage offers lifejackets, a leapfrog mat, and yard games for entertainment!

Outdoor spacesLocationPool

4.88 out of 5 average rating, 158 reviews

A front deck offers a view of a serene private lake, bordered by tall trees. A path leads down to the water, while a grassy area and seating can be seen nearby, providing a peaceful outdoor space.

Cottage in Montgomery

The Cottage at Pine Lake

Take a break & unwind at this peaceful oasis. Kayak, catch a fish, take a swim in the pool across the street or just relax on the front deck and watch the birds. Great location on private lake with pier. Close to local Montgomery wedding venues( Lumineer 2 min, Pine Lake Ranch 5min) Short drive to Margaritaville resort. Spend the day on beautiful Lake Conroe, bring your boat/ jet ski and launch down the road at the marina. Short drive to Sam Houston national forest to enjoy nature and hiking

Outdoor spacesLocationGrill

A fire pit area is surrounded by a circular seating arrangement featuring five black Adirondack chairs. The space is illuminated by overhead string lights, casting a warm glow over the grassy lawn and gravel pathway leading to the firepit.

4.98 out of 5 average rating, 128 reviews

New Lake House by Golf course + Kayaks & Game Room

Welcome to THE LAKE HOUSE - our spacious and welcoming getaway. Here you'll enjoy all the luxuries with an added plus of fun and activities. Whether your looking for some fun in the sun or a stay-cation at the Lake, you will find this to be your perfect destination. We have immediate access to the lake, Walden Golf course, and driving range. Looking to work from home? We got you covered. Looking for a fun-filled night in? Our game room has you covered - no cheating or whining allowed ; )

ValueOutdoor spacesDecor

Superhost

The open-concept living space features a dining area with a large wooden table and black chairs. Large windows invite natural light and showcase views of the lake and dock. A comfortable blue armchair and two ceiling fans add to the room's welcoming ambiance.

Home in Willis

4.97 out of 5 average rating, 124 reviews

Lake House- dock, hot tub, kayaks, screened porch

Located on the shores of Lake Conroe, Lee Shore Lake House offers an idyllic getaway for anyone! The open concept living area features large windows for natural light, offering breathtaking views of the lake. Gather around the dining table for a meal with loved ones. Prepare home-cooked meals in our fully equipped kitchen. Enjoy your morning coffee on the deck overlooking the lake. Go fishing from the dock or embark on a kayaking adventure. Come experience the magic of lakeside living!

LocationValueCheckout

Luxe

The exterior of a uniquely designed home on stilts is surrounded by trees, featuring a spacious deck with seating. A gentle slope leads to a private pond at the base, with lush greenery and a clear sky in the background, creating a serene lakeside setting.

Treehouse in Montgomery

4.98 out of 5 average rating, 181 reviews

Unique Lux Treehouse: Lakefront, Gameroom, Kayaks

Escape w/ the family to "Iron Pine Treehouse" next to Lake Conroe on a small private lake. Enjoy lake views from nearly every room w/ luxury finishes. Trees intersect the deck--a canopy of leaves overhead for a treehouse effect! 13 beds, sleeps 17 comfortably: 1 King, 2 Queens, 9 Twin bunks, 1 queen sofa bed Kayaks/Paddleboards and a game-room. There's even a connected studio with a full kitchen! Fish off the private dock | Only 3 minutes to Lake Conroe public boat ramp or boat rentals!

Outdoor spacesLocationCheck-in

Superhost

A spacious, two-story waterfront home is presented, featuring a covered deck with ample seating options. Lush green lawn surrounds the space, complemented by a wooden walkway leading to the entrance. The upper balcony showcases additional seating, enhancing outdoor relaxation opportunities.

4.88 out of 5 average rating, 101 reviews

Gorgeous Waterfront Lake Conroe Home Sleeps 10

This waterfront home offers all of the comforts of home perfectly situated on the water in a beautiful country club neighborhood. You will have access as our guests to the pool, gym, restaurant for a fee per Club Corp. Offering three large, spacious bedrooms each with full bathrooms and walk in closets. A fully equipped kitchen opens up to a family dining room overlooking the water. Guests may use our covered boathouse; this is a single slip with a lift and a 5,000 lb max.

Outdoor spacesLocationHospitality

4.98 out of 5 average rating, 119 reviews

A fire pit area is surrounded by log seating, inviting relaxation under string lights. The tiny cabin is visible nearby, nestled among tall trees. This setting provides a serene atmosphere, perfect for gatherings or enjoying evenings by the fire.

Cabin in Montgomery

Lake Cabin in the Forest - Houston National Forest

This is a great place to relax and unwind while enjoying the beautiful sunset and sunrise at the lake in Sam Houston National Forest with the geese, the ducks, and the birds, and keeping an eye out for the deer enjoying the lake. There's plenty of yard for your furbabies to enjoy. There's lots of scenery on the drive to the cottage (forests, wildlife, lakes, countryside, wineries, farms, wedding venues, etc.); you never know what you can capture, so bring your camera.

LocationOutdoor spacesIndoor spaces

4.9 out of 5 average rating, 144 reviews

An inviting living area features a comfortable sofa with accent pillows and a decorative coffee table. A ceiling fan provides airflow, while natural light enters through large windows. The open layout connects to a dining space, highlighted by wooden accents and a welcoming atmosphere.

Bungalow in Montgomery

Pinterest Worthy Lakefront Cottage

Lakefront on private lake, fully updated, open-concept Consistent 5-star Superhost property — professionally cleaned and accurately represented. Kayak, fish, or watch lake wildlife from front porch. Enjoy our grill, fire pit, outdoor sofa, and dining table on our very private patio. For your enjoyment: 3 smart TVs, dedicated desk space, wifi, kayaks, fishing poles, fully stocked coffee / tea bar. Closeby: Lake Conroe, Margaritaville, restaurants, shopping.

LocationValueLayout

4.92 out of 5 average rating, 146 reviews

The living area features comfortable leather recliners facing a wall-mounted television and an electric fireplace. A dining table is visible in the background, with a ladder leading to a loft area above. Natural light streams through multiple windows adorned with blinds.

Tiny home in Willis

Luxury Tiny House in Lake Resort

This unforgettable location is anything but normal. Luxury awaits you in your very own lake resort Tiny Home! Try out a Lake Community for Tiny Homeowners and have fun on the lake with tons of resort amenities along with your boat. Close to I-45 & 20 minutes to world-class dining & shopping. Bring the boat and your fishing poles. We guarantee you'll have a great time because lake life is the best life. Furthermore, we are a DOG -friendly resort!.

LocationOutdoor spacesCleanliness