Luxury Vacation Rentals with a Private Pool in Greenwood

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 1 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Greenwood

Home in Greenwood

4 bedrooms•3 baths

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New

Welcome to private poolside luxury in Greenwood

Retreat to your own private oasis in Greenwood with Wander. Our collection of luxury private-pool vacation rentals in Greenwood blends the polish of a five-star stay with the comfort of a beautifully designed home.

Each residence centers around a secluded pool scene with spacious decks, lounge seating, and easy indoor to outdoor flow. Many offer heated pools, alfresco dining, and fire features for year-round enjoyment in the Midwest. Inside, expect chef-ready kitchens, plush linens, ultra fast WiFi, dedicated workspaces, and optional fitness or game rooms, all backed by pristine cleaning and 24/7 concierge service.

Book knowing the home matches the photos and every detail works the way it should.

Available soon in Greenwood

Home in Greenwood

4 bedrooms•3 baths

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New

All homes in Greenwood

Home in Greenwood

4 bedrooms•3 baths

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New

View all homes

Highlights in Greenwood

Discover Greenwood's charm through its vibrant shopping districts, family-friendly water parks, scenic golf courses, and historic downtown spaces.

Greenwood Park Mall

Freedom Springs Greenwood Aquatics Park

Old Town Greenwood

Craig Park

Mallow Run Winery

Otte Golf & Family Fun Center

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for private pool vacation rentals in Greenwood

Outdoor dining area (1)

Other popular amenities & vacation types in Greenwood

Family vacation rentals in Greenwood

Large group vacation rentals in Greenwood

Pet-friendly vacation rentals in Greenwood

Hot tub vacation rentals in Greenwood

Discover more beyond the pool in Greenwood

Set just south of Indianapolis, Greenwood balances small-city ease with abundant green space. Walk the Tracy Trail, unwind by the creek at Old City Park, and cool off at Freedom Springs slides and lazy river.

Afternoons invite tee times at Valle Vista, boutique finds along Madison Avenue, and a visit to Greenwood Park Mall. With farmers markets, seasonal festivals, and swift access to downtown Indy for sports or arts, you can shape each day to your pace. This is why Wander's luxury private-pool vacation rentals in Greenwood are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Greenwood

Why should I book a Wander in Greenwood over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Greenwood delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Greenwood?

Some of our most popular private pool vacation rentals in Greenwood include Greenwood Gem | Pool, Hot Tub, Arcade | S10 and Greenwood Gem | Pool, Hot Tub, Arcade | S10. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Greenwood?

Wander offers 1 private pool vacation rentals in Greenwood, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Greenwood?

You can check-in to Wander private pool vacation rentals in Greenwood after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Greenwood have WiFi access?

Yes. Every Wander home in Greenwood has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.