Vacation rentals with a pool in Westfield

Hallmark-Style Holiday Estate Near Chriskindlmarkt

Westfield's top vacation property! Woodside Retreat is a truly special 4 acre historic estate. The property is one of a kind for the area, blending a history that dates back to 1861 with modern touches and amenities. This Indiana farmhouse, with ties to the Underground Railroad, has been thoughtfully furnished with comfort and heritage in mind. Imagine making memories with family, colleagues, or friends with an entertainment barn, in-ground pool/deck, pergola, fire pit, & beautiful open space.

Absolute GEM! 5 Mins Grand Park, Spacious Backyard

Westfield gem! Just 7 quick minutes to Grand Park! Close to Downtown Indianapolis (32 mins), Ruoff Music Venue (27 mins) and all that the Indianapolis & surrounding areas have to offer. Spacious 4-bed, 2.5-bath home sleeps 11 guests comfortably. Includes beautiful fully stocked kitchen, 2-car garage, TVs, Movie Theatre, games, fenced backyard, and patio for your enjoyment! Stroll on the Monon Trail. Enjoy family-friendly parks. So many restaurants to choose from, too! Your seamless stay awaits!

Peaceful & Luxurious Suite

Our guest suite is close to Indpls--approx. 20 min from downtown. You’ll love our place because of the quiet & serene environment that's just outside of the city. We sit on an acreage close to the I70/Mt Comfort Road Exit making for quick access to and from the interstate. Our suite is in the front corner of our home. It has a private entrance with porch. It looks out into a garden that has a pond with fountain along with seating under a pergola. It has high ceilings and is very spacious.

Charming 2 bedroom condo downtown

Experience our charming home in The Old Northside, one of Indianapolis' most desirable neighborhoods, where comfort meets convenience. This 1 bedroom residence features a shared outdoor pool, a prime location close to downtown attractions and dining. Families will benefit from a kids' park and playground just across the street. With its rich history and modern amenities, this home offers a vibrant lifestyle. Don't miss the opportunity to make it yours in a neighborhood that truly has it all.

20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym

Welcome to Whitestown, IN — proudly hosted by TIBO Ventures. Standout Features: • Modern *2-BR, 2-BA* with stylish decor • Fully equipped kitchen w/ new appliances & quartz countertops • Both bedrooms king-size beds and walk-in closets for max comfort • Private balcony for relaxing Amenities: ✔ 24-Hour Gym ✔ Pickleball Courts & Pool ✔ Built-in Desk for remote work ✔ Pet-Friendly community with Dog Park ✔ High-Speed Fiber Internet ✔ Close to dining and shopping ✔ Free On-site Parking

Serene 1BR: Perfect Indy Stay

Welcome to your ideal retreat in Whitestown, Indiana! Our modern 1-BR apartment is perfect for short or extended stays. Enjoy a bright living area, fully-equipped kitchen, and cozy bedroom with a queen-sized bed. Amenities include high-speed Wi-Fi, an in-unit washer and dryer, central heating and AC, free parking, a fitness center, and a pool. Conveniently located near dining, shopping, and just 20 minutes from downtown Indianapolis. Book now for a comfortable and convenient stay!

Minutes from Grand Park

3 bedroom + study with twin trundle bed and gaming station; 2 bath located in quiet neighborhood, minutes from Grand Park Sports Campus. Sleeps 8; designated work space; 1 Gig internet; washer/dryer. Open living room and kitchen connected by a built-in island and custom bench seating. Private fenced back yard for relaxing. Enjoy adjacent Midland-Trace trail for a leisurely walk to nearby grocery and restaurants or the neighborhood playground and pool just a 2 min walk away.

IRIE Living Grand Park Lux 2BR w/ King Bed + Gym

Welcome to Your Ultimate Stay in Westfield, IN! Make yourself at home in this spacious and modern 2-bedroom apartment, perfect for families, business travelers, and sports enthusiasts visiting Grand Park Sports Complex. With top-tier amenities and a prime location, your stay will be as comfortable as it is convenient. MANAGEMENT REQUIRES ALL GUESTS TO COMPLETE A BACKGROUND CHECK FOR VERIFICATION. The unit is on the second floor, which is easily accessible by stairs.

Game Room, Pool & Hot Tub|Sleeps 14 | Pet Friendly

Welcome to Your Perfect Getaway! This stunning two-story home offers the ideal combination of comfort, luxury, and functionality. There’s plenty of room for family. Inside, you'll enjoy expansive living areas. This home provides the space and comfort you need for a memorable stay. Step outside into your private, fully fenced backyard oasis. Cool off in the pool on warm summer days, or unwind in the hot tub under the stars. Your personal retreat awaits.

Traders Point Retreat w/ Pool, Hot Tub & Fire Pit

Welcome to your Zionsville retreat, Traders Point Countryside - perfect for families, friends & group getaways! Set on 2 peaceful acres, this spacious home combines comfort w/ resort-style amenities: *Heated saltwater pool (May-Oct) & hot tub *Fire pit, BBQ grill, patio & tree swings *Game room w/ foosball & Smart TV *Chef’s kitchen w/ coffee station *Family-ready: crib, pack ’n play, toys, high chair *Sleeps 15 across 3BR + sofa bed

King Bed - 1B/1BTH - POOL

BRAND NEW upscale one bedroom apartment with king bed. Minutes away from Downtown Fishers. Complex is conveniently located next to nature preserve, walking path & Nickel Plate Trail. Enjoy the amazing amenities: Pool, hot tub, fitness center, business center, clubhouse lounge & outdoor grilling space. 10mins away from Ruoff Music Center. Note: POOL AND HOT TUB ARE DURING SUMMER MONTHS ONLY. (FROM MEMORIAL DAY THROUGH LABOR DAY)

Stylish Stay | Near Everything!

Welcome to your perfect getaway! This stylish 2-bed, 2-bath unit features a king-size bed, smart TV, and private bathroom in the master suite, plus a cozy queen bed in the second room. Enjoy a second full bathroom, smart TV in the living room, a private balcony with lovely views, fully stocked kitchen, in-unit laundry, and a warm, inviting living space. Ideal for short- or long-term stays—comfort and convenience await!