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Resort vacation rentals in Madison

Find and book unique resort rentals on Airbnb

Quick stats about resort rentals in Madison

Total vacation rentals
Explore 50 vacation rentals in Madison
Nightly prices starting at
Madison vacation rentals start at G$16,732 GYD per night before taxes and fees
Verified guest reviews
Over 70 verified reviews to help you choose
Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities
Vacation rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
50 of Madison vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Madison rentals
4.6 Average rating
Madison stays receive an average rating of 4.6 out of 5 from guests

Top-rated resort rentals in Madison

Guests agree: these resort rentals are highly rated for location, cleanliness, and more.

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Resort in Nashville

New place to stay

CW-Nashville 2-bdrm, 2-bath 1 mile Grand Ole Opry

Southern traditions of hospitality & charm, you’ll want for nothing as you adventure day/night in Music City. This warm, friendly resort is close to Nashville’s best music, liquor, & historical landmarks. 1-mile from Grand Ole Opry, CW Nashville provides a great base to explore all the middle Tennessee has to offer. Located near the Country Music Hall of Fame, Museum & Nashville Zoo. A scenic drive to Jack Daniel’s Distillery Parking is free. nearest grocery store is five miles from the resort.

An expansive view captures a sparkling outdoor swimming pool lined with lounge chairs and colorful landscaping. The city skyline is visible in the background, showcasing a mix of modern buildings and greenery under a bright blue sky.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

You won’t have to head all the way to the Caribbean to find your lost shaker of salt. In fact, it’s right upstairs at the resort’s rooftop bar. Lounge poolside until the sun hangs low, take it easy by the fire pit, and see panoramic views of downtown as live music loosens your mood. Wyndham Marg Vacation Club Nashville|King Studio • Size: 400 - 554 • Kitchen: Mini • Baths: 1 - Standing Shower no tub • Accommodates: 4 Guests • Beds: Double Sleeper Sofa - 1 King Bed - 1

LocationValuePool

A wide view of the outdoor swimming pool is captured, surrounded by lounge chairs. The pool area is complemented by colorful landscaping and a backdrop of modern buildings under a clear blue sky.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

You won’t have to head all the way to the Caribbean to find your lost shaker of salt. In fact, it’s right upstairs at the resort’s rooftop bar. Lounge poolside until the sun hangs low, take it easy by the fire pit, and see panoramic views of downtown as live music loosens your mood. Wyndham Marg Vacation Club Nashville|King Studio • Size: 400 - 554 • Kitchen: Mini • Baths: 1 - Standing Shower no tub • Accommodates: 4 Guests • Beds: Double Sleeper Sofa - 1 King Bed - 1

LocationIndoor spacesNearby

A modern kitchen area features dark wooden cabinetry and a granite countertop, complemented by stainless steel appliances. An open layout connects to a cozy living space with a dining table and seating by a window, allowing for natural light to brighten the room.

Resort in Nashville

5.0 out of 5 average rating, 5 reviews

Nashville Getaway and Fun Trip

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Located just one mile from the Grand Ole Opry. Conveniently located near popular destinations like the Country Music Hall of Fame and Museum and the Nashville Zoo, you can easily explore all that Nashville has to offer.

LocationCleanlinessHospitality

An outdoor swimming pool is surrounded by lounge chairs and umbrellas, providing a space for relaxation. Apartment buildings are visible in the background, with some featuring balconies that overlook the pool area. A clear blue sky with fluffy white clouds enhances the atmosphere.

Resort in Nashville

4.65 out of 5 average rating, 17 reviews

Wyndham Nashville Resort | 2BR/2BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 2BR/2BA King Bed Suite • Size: 1066 - 1180 • Kitchen: Full • Baths: 2 • Accommodates: 6 Guests • Beds: King Bed - 1 Queen Sleeper Sofa - 1 Varies

LocationValuePool

An outdoor swimming pool is surrounded by a spacious deck furnished with lounge chairs. Blue umbrellas are positioned to provide shade, and several trees are visible in the background, enhancing the resort's inviting atmosphere.

Resort in Nashville

4.8 out of 5 average rating, 5 reviews

Wyndham Nashville Resort | 2BR/2BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 2BR/2BA King Bed Suite • Size: 1066 - 1180 • Kitchen: Full • Baths: 2 • Accommodates: 6 Guests • Beds: King Bed - 1 Queen Sleeper Sofa - 1 Varies

HospitalityIndoor spacesAmenities

An outdoor swimming pool is surrounded by a deck lined with blue lounge chairs. Umbrellas provide shade for several seating areas. Multi-story buildings with balconies can be seen in the background, under a clear blue sky accented by fluffy white clouds.

Resort in Nashville

Wyndham Nashville Resort | 3BR/3BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 3BR/3BA King Bed Suite • Size: 1605 - 1671 • Kitchen: Full • Baths: 3 • Accommodates: 8 Guests • Beds: King Bed - 2 Queen Sleeper Sofa - 1 Varies

An outdoor swimming pool is surrounded by lounge chairs featuring blue canvas fabric. Umbrellas provide shade around the pool area, while light clouds drift across a bright blue sky, adding to the inviting atmosphere of the resort.

Resort in Nashville

Wyndham Nashville Resort | 3BR/3BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 3BR/3BA King Bed Suite • Size: 1605 - 1671 • Kitchen: Full • Baths: 3 • Accommodates: 8 Guests • Beds: King Bed - 2 Queen Sleeper Sofa - 1 Varies

An outdoor swimming pool is surrounded by lounge chairs under blue umbrellas. The pool area includes a concrete deck with a smooth surface, while nearby buildings provide a backdrop of residential charm.

Resort in Nashville

Wyndham Nashville Resort | 3BR/3BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 3BR/3BA King Bed Suite • Size: 1605 - 1671 • Kitchen: Full • Baths: 3 • Accommodates: 8 Guests • Beds: King Bed - 2 Queen Sleeper Sofa - 1 Varies

An outdoor pool area is framed by lounge chairs and shaded umbrellas. The clear blue water of the pool reflects the sky and nearby buildings, creating a relaxing atmosphere for guests. Surrounding greenery adds a touch of nature to the setting.

Resort in Nashville

Wyndham Nashville Resort | 3BR/3BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 3BR/3BA King Bed Suite • Size: 1605 - 1671 • Kitchen: Full • Baths: 3 • Accommodates: 8 Guests • Beds: King Bed - 2 Queen Sleeper Sofa - 1 Varies

An outdoor swimming pool is surrounded by lounge chairs with blue cushions, offering ample seating for relaxation. Umbrellas provide shade over the seating area. Nearby, light-colored buildings offer a backdrop, while fluffy clouds drift across a bright blue sky.

Resort in Nashville

4.6 out of 5 average rating, 10 reviews

Wyndham Nashville Resort | 1BR/1BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 1BR/1BA King Bed Suite • Size: 928 - 988 • Kitchen: Full • Baths: 1 • Accommodates: 4 Guests • Beds: King Bed - 1 Queen Sleeper Sofa - 1 Varies

LocationFamilyCleanliness

A clear blue swimming pool is surrounded by lounge chairs, with vibrant blue umbrellas providing shade. Multiple residential buildings are visible in the background against a sunny sky dotted with fluffy clouds.

Resort in Nashville

4.69 out of 5 average rating, 13 reviews

Wyndham Nashville Resort | 1BR/1BA King Bed Suite

Steeped in Southern traditions of hospitality and charm, you’ll want for nothing as you adventure day and night in Music City. Luckily, this warm, friendly resort is close to Nashville’s best music, liquor, and historical landmarks. Wyndham Nashville Resort | 1BR/1BA King Bed Suite • Size: 928 - 988 • Kitchen: Full • Baths: 1 • Accommodates: 4 Guests • Beds: King Bed - 1 Queen Sleeper Sofa - 1 Varies

ValueLocationCheck-in

Popular amenities for Madison resort rentals

Free parking on premises

Air conditioning

Family-friendly resort rentals

An expansive outdoor swimming pool is featured with lounge chairs positioned along its perimeter. The pool area is surrounded by landscaped greenery. In the background, a skyline of downtown buildings is visible under a clear blue sky.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

LocationGetting around

An outdoor pool area is surrounded by lounge chairs and umbrellas. The pool features a clear blue surface, inviting guests to relax. Nearby, buildings with balconies provide a backdrop, while fluffy clouds drift in a blue sky.

Resort in Nashville

Wyndham Nashville Resort | 3BR/3BA King Bed Suite

An outdoor swimming pool is surrounded by lounge chairs and umbrellas, creating a relaxing atmosphere. The pool reflects the sky, and nearby buildings feature balconies that overlook the area. Light clouds drift overhead, enhancing the leisurely setting.

Resort in Nashville

Wyndham Nashville Resort | 1BR/1BA King Bed Suite

A spacious outdoor swimming pool is surrounded by numerous lounge chairs under bright blue umbrellas. The resort buildings, with multiple balconies, frame the pool area, set against a backdrop of clear blue skies and fluffy white clouds.

Resort in Nashville

3.67 out of 5 average rating, 3 reviews

Wyndham Nashville Resort | 2BR/2BA King Bed Suite

ValueCleanlinessHot tub

A panoramic view displays the outdoor swimming pool surrounded by sun loungers, with vibrant landscaping and decorative flowers. The skyline of downtown Nashville and neighboring buildings are visible in the background under a clear blue sky.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

LocationCheck-inCleanliness

The outdoor swimming pool is highlighted, surrounded by lounge chairs in a refreshing blue hue. The surrounding area features vibrant landscaping and offers views of the city skyline, with buildings visible in the distance under a clear blue sky.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

An expansive outdoor pool area is visible, featuring several lounge chairs arranged along the water's edge. The surrounding urban landscape includes modern buildings and greenery, with a clear blue sky overhead.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

A clear view reveals an outdoor swimming pool surrounded by lounge chairs and tropical landscaping. The backdrop features a skyline of downtown Nashville with various buildings and open spaces under a bright blue sky.

Resort in Downtown Nashville

Wyndham Marg Vacation Club Nashville|King Studio

Resort rentals with a pool

Resort in Nashville

5.0 out of 5 average rating, 3 reviews

Wyndham Nashville - 2 Bedroom Condo

LocationValueIndoor spaces

Resort in Nashville

4.75 out of 5 average rating, 4 reviews

Nashville Resort - 2 Bedroom Condo

ValueLocationCondition

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

Location

Resort in Nashville

Wyndham Nashville - 1 Bedroom Suite

Resort in Nashville

Wyndham Nashville - 1 Bedroom Suite

CleanlinessComfortCheck-in

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

Resort rentals with a gym

Resort in Nashville

Nashville • Live Music + Pool • 2Br Condo

LocationGetting aroundCondition

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

LocationCleanliness

Resort in Nashville

Wyndham Nashville - 1 Bedroom Suite

FamilyAccuracy

Resort in Nashville

Wyndham Nashville - 1 Bedroom Suite

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

Resort in Nashville

Wyndham Nashville - 1 Bedroom Suite

LocationLayoutAccuracy

Resort in Nashville

Wyndham Nashville - 2 Bedroom Condo

Resort in Nashville

4.33 out of 5 average rating, 6 reviews

Wyndham Nashville - 1 Bedroom Suite

LocationValueComfort

Destinations to explore