Holiday rentals with a pool in Winston County

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Top-rated rentals with a pool in Winston County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Cullman

4.94 out of 5 average rating, 88 reviews

Mallard Pointe Overlook

Welcome to your peaceful retreat on the lake! This spacious condo sits on the top floor, offering breathtaking, unobstructed views of the lake. Whether you’re sipping coffee at sunrise or winding down with a sunset, the scenery is unmatched. Located in a quiet, community with access to two sparkling pools, this is the perfect spot for families, couples, or groups looking to relax and recharge. Inside, you’ll find an open layout, private bathrooms for each bedroom, and all the comforts of home.

Home in Crane Hill

5 out of 5 average rating, 4 reviews

Panoramic views in Silverock, Crane Hill, AL

Only steps from the water, this 4 bdrm, 3.5 bath house (plus new loft daybed) is located on a spacious end-of-the-point lot in Silverock Cove, a gated community on Smith Lake featuring two pools and picturesque boardwalks. Our home has wraparound water views from every room with a great porch and stone patio with fire pit to take it all in! Whether your looking for a quiet, relaxing getaway with friends or a fun family trip out on the water, this is the place. 7 day rental required by our HOA.

Guest favourite

Home in Crane Hill

4.95 out of 5 average rating, 21 reviews

Serenity Sunsets - Smith Lake

Welcome to our stunning and luxurious lake bungalow retreat! This rental offers the perfect blend of relaxation and entertainment. Situated on a hilltop with long range lake views and breathtaking sunsets that will leave you in awe. Step outside and indulge in the ultimate outdoor experience. Take a refreshing dip in the sparkling pool, work on your short game at the custom putting green, play ping pong on the turf lawn and as the sun sets gather around the fire pits! (*$150/day to heat pool)

Guest favourite

Home in Crane Hill

5 out of 5 average rating, 10 reviews

Luxury on Smith Lake 5BR/3.5BA, Steps to Water!!

Welcome to the oasis of Mandolin Rain Cabin in the private, gated and family oriented development of Point William at Smith Lake! Our home is absolutely the best vacation layout you will find anywhere. Two levels of elevated lakefront living, elegance and class with 5BR/3.5BA, equally generous spaces indoors and out. Luxury designer furnishings, bedding and finishes will delight. 4 King beds in 4 spacious bedrooms and 4 twin bunks in 5th bedroom. Many lake toys come with this home rental!

Superhost

Home in Crane Hill

4.93 out of 5 average rating, 73 reviews

All 'Decked' Out - Optional Boat rental delivered

Amazing lakefront home on Smith Lake with beautiful views and access to year round water. Our house is located at the end of an inlet, so the area is cozy and calm. You will be only a few steps from Smith Lake and a walk to the neighborhood pool. The main level of the house hosts an open concept with an eat in kitchen and living area. The house also consists of a screened in porch with majestic views of the water, a swim up pier, and a double slip boat dock. Pontoon Boat Rental available.

Guest favourite

Home in Cullman

4.93 out of 5 average rating, 45 reviews

Private Heated Pool, Fishing Pond, 10 acre retreat

"Sweet Home Alabama" is a new construction, modern, high end home completed in 2022, situated on 10 private, secluded, gated acres. The home itself has 4 bedrooms and 3.5 baths. Amenities include private heated pool, 2 person sauna, semi-private championship bass fishing pond, gravel fishing beach with peddle boat, firepit with supplied wood and tons of seating, spaces for camping and room for hiking and exploring. Its like your own campground complete with high end home and private pool!

Top guest favourite

Apartment in Jasper

4.94 out of 5 average rating, 54 reviews

Beautiful Lakefront Condo with Pool and Boat Slip

Come enjoy the fresh air and relax at Smith Lake. This recently renovated 3 BA/2 BA condo features a gorgeous lakefront view from both the living room and main room. Duncan Bridge Resort is a gated complex with a community pool exclusively for owners and guests. Each unit also has its own assigned boat slip available to you during your stay. This condo sleeps 6. Bedroom #1 Main: King size bed with an en-suite bathroom Bedroom #2 Guest: 2 Twin size beds Bedroom #3 Guest: 2 Twin size beds

Guest favourite

Guest house in Crane Hill

4.95 out of 5 average rating, 103 reviews

Tiny Heaven Pet Friendly

This tiny home is one of a kind .. once an Amish shed that has been transformed into an artful piece of heaven.. The home is directly across the street from beautiful Smith Lake. We have a shared pool and boat dock with two other rentals .. kayaks are available for you to enjoy. The house is not directly on the water but you will have access to a golf cart to get to dock! We are pet friendly.. please select pet fee option at booking … No more than 2 can occupy the property at anytime.

Guest favourite

Home in Vinemont

4.86 out of 5 average rating, 7 reviews

Vacation House with Pool

Relax by the pool with the entire family! There are three bedrooms. The master suite has its own private full bathroom and a king size bed. The location of the house is perfect. Only 7 miles to Hurricane Creek Park(hiking), 10 minutes to restaurants and shopping, and 1 hour from major cities like Huntsville and Birmingham. We are also Pet-Friendly! Feel free to message me with any questions or inquiries about the property. We offer great discounts on week or month long stays!

Guest favourite

Cottage in Crane Hill

4.92 out of 5 average rating, 38 reviews

Luxury Lakefront Cottage w/ Kayaks and SUPs

Welcome to your luxury lakefront cottage in a private gated community! This custom home on the neighborhood’s premier point lot has 5 bedrooms, 3.5 baths (sleeping for 14 guests), 2 living rooms, and boasts pristine 270 degree lake views, from nearly every room. Enjoy a true cozy lake vacation feel with designer and RH decor, private boat dock, 4 kayaks, 3 SUPs, outdoor kitchen, and Adirondack-surrounded fire pit all nestled among the trees!

Guest favourite

Apartment in Cullman

4.95 out of 5 average rating, 66 reviews

The Queen Bee

If a great view and creature comforts are important to you , the Queen Bee overlooking Smith Lake is your home away from home. Located 7 miles from I-65. (6 guest maximum), Each BR has private bath, TV. An electric FP in family room for warm cozy. Fully equipped kitchen. No step entry. Cleats to tie up your boat and a ladder to make swimming in lake available. The infinity pool is both unique and beautiful (seasonal).

Apartment in Crane Hill

Top Deck Retreat on Smith Lake

Relax with the whole family at this peaceful place to stay and enjoy the lake view! Complete with a spacious patio deck to enjoy beautiful sunsets, and a dock with deep water for swimming fun. Comes with all the amenities one may need! Wifi, Smart TV, fully equipped kitchen, swimming pool, and a gas community grill. Enjoy the Lake or take a short drive into Cullman for dining, shopping, and local activities.