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Vacation rentals with a pool in Madison Heights

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Madison Heights

  • Total vacation rentals

    Explore 20 vacation rentals in Madison Heights

  • Nightly prices starting at

    Madison Heights vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Madison Heights vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madison Heights rentals

  • 4.8 Average rating

    Madison Heights stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Madison Heights

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

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Guest favorite
The exterior of a two-story townhouse is shown, featuring white siding and blue window shutters. A walkway leads to the entrance, where a star decoration is placed above the door. Surrounding greenery includes shrubs and trees, providing a well-kept appearance.
Townhouse in Lynchburg

Large Comfy Getaway Near Liberty! Your Home Away.

Come visit our large, end unit townhome in Lynchburg, near Liberty U and Peaks View Park! 5 bedrooms, 3 bathrooms, lots of space for the whole family! Fully stocked kitchen w/ separate dining space and outdoor deck seating and grill. We’ve got a pool table, board games, Roku TV’s, and toys for the kids. Pack N play & high chair available for infants. Excellent location, in the middle of it all! Make yourself at home, theres everything you need! Neighborhood swimming pool open seasonally!

FamilyValueCheck-in

4.9 out of 5 average rating, 105 reviews
Top guest favorite
A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.
Home in Wintergreen Resort

Bear's Mountain Escape

Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

FamilyValuePets

4.95 out of 5 average rating, 170 reviews
Top guest favorite
An open living area features a stone fireplace with a mounted TV above and large windows that provide a panoramic view of the lake. A round glass dining table is set near the window, complemented by a cozy sofa and armchair, inviting relaxation and gatherings.
Condo in Moneta

Fun Lake Getaway with Breathtaking Views

Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

LocationFamilyOutdoor spaces

4.99 out of 5 average rating, 322 reviews
Top guest favorite
A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.
Home in Nellysford

151Escape | 5 Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

LocationFamilyParks

4.99 out of 5 average rating, 173 reviews
Superhost
The kitchen area features light blue walls and modern black cabinetry. A spacious countertop is accompanied by two bar stools and stainless steel appliances. Natural light filters in through a window, creating striped shadows across the floor, enhancing the open feel of the space.
Home in Lynchburg

Lynchburg Midtown Lofts Garage Conversion

Formally a garage, this property has been transformed into a trendy two bedroom home! Located on premises at The Midtown Lofts, you can enjoy all of the amenities the property has to offer. Pool, fitness center, beach volley ball court, fire pit and the private movie theater. Pool is seasonal. The large windows allow all of the natural light you want! Two full-size beds. There is also a work space for those of you who are traveling for business, but please try to have some fun as well!

ValueFamilyWifi

4.81 out of 5 average rating, 402 reviews
Top guest favorite
A breathtaking sunset casts vibrant shades of orange, pink, and purple across the lake's surface. Silhouetted docks extend into the water, framed by distant mountains and a softly illuminated sky, creating a serene lakeside scene.
Condo in Moneta

Lake Lover's Paradise

Come to the lake! This spacious one bedroom top floor end unit is uniquely located between Napoli by the Lake restaurant and large outdoor swimming pool. Fantastic views of the lake from the large deck! Sleeps 2 adults and 2 small children under three. The following amenities are provided during your stay (Subject to season and repair): 2 Outdoor Pools Exercise Room Boat & Jet Ski Rental 1 Indoor Pool Hot Tub Courtesy Boat Slips Beach & Boat Launch Area Tennis & Pickleball Courts

LocationFamilyCheck-in

4.99 out of 5 average rating, 400 reviews
Top guest favorite
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

FamilyLocationCheckout

4.98 out of 5 average rating, 233 reviews
Top guest favorite
Home in Wintergreen Resort

Cliffs Edge - It’s Pumpkin Spice Time!

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

LocationFamilyCheck-in

4.97 out of 5 average rating, 130 reviews
Superhost
A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.
Condo in Wintergreen Resort

1 bedroom condo, close to hikes & breweries & pool

Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.

LocationValueAmenities

4.92 out of 5 average rating, 216 reviews
Top guest favorite
A hot tub bubbles invitingly on a concrete pad in a spacious yard. Surrounding the tub is a well-maintained green lawn, with majestic mountains visible in the background. White Adirondack chairs are positioned nearby for relaxing moments outdoors.
Home in Nellysford

Spacious retreat: Game Room, Hot Tub & Fire Pit

Gather family & friends for a memorable getaway at The Myrtle at Wintergreen. This spacious golf-course retreat combines luxury, comfort and exceptional amenities minutes from Nelson 151 wineries, breweries, hiking, golf and Wintergreen Resort. 💦 Hot tub 🎱 Game room with pool, ping pong, foosball & air hockey 🛏️ Sleeps 10 with 2 Kings, 1 Queen & 2 Full (each with TV) 🔥 Screened porch, fire pit, BBQ ⚡ EV charger 🏊 Community pool, tennis & pickleball 🚗 40 minutes to Charlott

LocationFamilyPool

5.0 out of 5 average rating, 113 reviews
Top guest favorite
A vibrant sunset casts warm hues across the sky, viewed from a covered outdoor area. The scene includes a fenced swimming pool and expansive green fields in the background, indicating a serene outdoor space perfect for relaxation.
Apartment in Forest

Large apartment w private pool / availability.

Beautiful, large 2 bedroom apartment with stunning sunset views. Full kitchen with Keurig Coffee, microwave, oven/stove, toaster, and refrigerator. The large family room has seating for 11 while you watch cable TV. Please NO SMOKING on these premises. Swimming pool MAY be available. The pool is our families, but it often works out that my guests can use it. You must communicate your wishes and we will see it's availability. An outdoor grill is available.

ValueFamilyGetting around

4.92 out of 5 average rating, 135 reviews
Guest favorite
Chalet in Lovingston

Secluded Cabin Pool + Trails & Firepit 12 ppl

Escape to a secluded mountain retreat in Lovingston, VA with 3BR + Loft, a spacious living area, and a private pool. Set beside 800 acres of hiking trails, this rustic yet comfortable home offers a Weber grill, fire pit, Sonos sound system, and fast WiFi. Relax by the pool, gather around the fire, or explore nearby wineries, breweries, and Charlottesville. Perfect for families, groups, and nature lovers seeking peace and adventure in the Blue Ridge.

FamilyValueGetting around

4.85 out of 5 average rating, 324 reviews

Popular amenities for Madison Heights rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.
Home in Wintergreen Resort

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 238 reviews
Guest favorite
A functional kitchen with wooden cabinetry and an island is featured. The space includes a stove, modern appliances, and a ceiling fan. A brick wood stove adds a rustic element, while a small plant sits on the island, providing a touch of greenery.
Home in Afton

Farmhouse on Working Vineyard

FamilyValueHiking

4.94 out of 5 average rating, 163 reviews
Top guest favorite
A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.
Home in Lovingston

Private Pool Opens April 1 - All Year Hot Tub

LocationValueAccuracy

4.96 out of 5 average rating, 240 reviews
Top guest favorite
The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.
Home in Wintergreen Resort

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

LocationFamilyWifi

4.9 out of 5 average rating, 162 reviews
Top guest favorite
Home in Wintergreen Resort

Retreat to the Canopy House: Firepit | EV | Trails

LocationValueCondition

4.99 out of 5 average rating, 114 reviews
Guest favorite
A single-story house with white vinyl siding is surrounded by well-maintained greenery. A front porch features a swing, while large windows invite ample natural light. The muted color palette of the exterior harmonizes with the inviting lawn space, creating a peaceful outdoor setting.
Home in Schuyler

Peaceful Cottage

FamilyLocationCondition

4.81 out of 5 average rating, 123 reviews
Top guest favorite
A spacious mountain estate is framed by bare trees in a serene winter setting. The exterior features a mix of light and dark wood siding, a welcoming front porch with seating, and an American flag gently waving. A gravel pathway leads up to the home.
Home in Wintergreen Resort

Walk to Ski! Mntn View DogsOK Pool Table Fireplace

ValueLocationKitchen

4.96 out of 5 average rating, 112 reviews
Superhost
A charming waterfront home is positioned on a sloping lot, surrounded by trees. The property features multiple outdoor decks and a covered porch, offering space for relaxation and enjoyment of the natural surroundings. Sunlight filters through the trees, highlighting the lush greenery.
Home in Moneta

Waterfront Fun at Smith Mountain Lake!

LocationFamilyHot tub

4.85 out of 5 average rating, 117 reviews

Condo rentals with a pool

Top guest favorite
A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.
Condo in Wintergreen Resort

3 BR 3 BA, 2 story condo in Highlands

ValueLocationKitchen

4.99 out of 5 average rating, 185 reviews
Superhost
Condo in Moneta

Bernards Landing NEXT2Pool (OpenTill 10/15 Heated)

FamilyLocationAir conditioning

4.76 out of 5 average rating, 123 reviews
Superhost
A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.
Condo in Wintergreen Resort

Tips Up: Cozy Slopeside Retreat w/ Fireplace

FamilyLocationLong stay

4.88 out of 5 average rating, 225 reviews
Guest favorite
A sandy beach area is bordered by calm waters. Shade is provided by tiki umbrellas, while a volleyball net is visible in the soft sand. Kayaks are placed on the shore, and green lawns extend in the background, leading to a serene lakeside view.
Condo in Moneta

Tranquility Cove Condo at Smith Mountain Lake

ValueLocationQuiet

4.96 out of 5 average rating, 132 reviews
Guest favorite
The exterior view captures a two-story mountain condo, featuring a welcoming wooden ramp leading to a deck. The brown wood siding complements the natural surroundings, and multiple windows allow for ample light. Seasonal decor embellishes the entry, enhancing the inviting facade.
Condo in Wintergreen Resort

Your Cozy Mountain Getaway Awaits

FamilyValuePool

4.8 out of 5 average rating, 110 reviews
Guest favorite
A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.
Condo in Wintergreen Resort

Ski-In Ski-Out ~ Mtn Views ~ King Suite

FamilyValueLayout

4.95 out of 5 average rating, 180 reviews
Guest favorite
Condo in Wintergreen Resort

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

ValueFamilyCheck-in

4.95 out of 5 average rating, 201 reviews
Top guest favorite
Condo in Wintergreen Resort

Extremely private, 2-min drive to skiing/hiking

ValueFamilyLayout

4.97 out of 5 average rating, 183 reviews

Other vacation rentals with a pool

Guest favorite
A stone path leads to a private dock, beside a calm lake framed by lush green trees. The vibrant red foliage of a nearby tree adds a pop of color against the serene backdrop of blue skies and water.
Vacation home in Moneta

Spacious Waterfront House for the perfect getaway

FamilyValueBathroom

4.88 out of 5 average rating, 118 reviews
Guest favorite
An open-concept living space is showcased, featuring a large flat-screen TV mounted on the wall. A comfortable couch and coffee table provide a cozy seating area, while a dining table with chairs is positioned nearby. Light wood accents and a patterned rug add warmth to the room.
Townhouse in Lynchburg

NEW! Beautiful Twnhme /Fitness/ Pool/ LU+Airport

ValueLocationCheckout

4.89 out of 5 average rating, 100 reviews
Guest favorite
A serene outdoor pool area is surrounded by lush greenery and tall trees. Lounge chairs and umbrellas provide seating, while a gazebo offers shaded space. The pool reflects the blue sky and sun rays, creating a bright and inviting atmosphere for relaxation.
Guest suite in Lexington

The Getaway

ValueFamilyNearby

4.97 out of 5 average rating, 148 reviews
Guest favorite
A modern kitchen is equipped with stainless steel appliances and a granite countertop. A pop of color is provided by a turquoise kettle and a 'HOME' sign above the cabinets. Soft lighting is cast from overhead fixtures, illuminating the workspace and creating a welcoming feel.
Apartment in Wintergreen Resort

Wintergreen Escape | King Bed + Porch Views

FamilyLocationPool

4.92 out of 5 average rating, 133 reviews
Guest favorite
A two-story home nestled among autumn-colored trees features a welcoming front entrance. A covered porch with steps leads to the door. Leaves carpet the driveway, and the building's exterior showcases a blend of warm tones and large windows that invite natural light.
Cabin in Wintergreen Resort

Stylish 7BR/16 pp Wintergreen Resort Home Ski/Hike

FamilyLocationWalkability

4.92 out of 5 average rating, 145 reviews
Top guest favorite
A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.
Villa in Wintergreen Resort

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

FamilyValueDecor

4.96 out of 5 average rating, 151 reviews
Top guest favorite
A bright bedroom showcases a spacious bed with crisp white linens and decorative pillows. A contemporary nightstand complements the room's style. Natural light filters through the window, while textured curtains add warmth. A vibrant area rug features geometric patterns beneath the bed.
Apartment in Lynchburg

Modern 1-Bed Condo: OPEN POOL with City Access

ValueLocationGetting around

4.96 out of 5 average rating, 55 reviews
Top guest favorite
A bright living area features a large sectional sofa, a round coffee table, and an accent chair. Tall windows allow natural light to fill the space, highlighting the unique design elements such as the ceiling fan and decorative wall art.
Condo in Lynchburg

Relax in Style | 2 KING Beds - *POOL* - PacMan!

FamilyValueSleep quality

4.95 out of 5 average rating, 86 reviews

Destinations to explore