Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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

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Top guest favorite

A formal dining room features a dark wooden table surrounded by six chairs. A vintage chandelier hangs above the table, complemented by large windows with dark drapes. An ornate fireplace with decorative accents adds character, while a cozy seating area includes a patterned armchair.

Apartment in St. Louis

4.93 out of 5 average rating, 231 reviews

Historic Victorian, Safe, Cozy 2nd Floor

Lalanea (Luh-Lane-Yah)Rating, 5 stars1 week ago

So lovely. Felt fancy and comfortable. I liked the neighborhood and the space. They thought of all kinds of little comforts. I will say if you have mobility issues, this would be a tough spot. Lugging stuff up the old, narrow, winding stairs was little challenging for this over 50 chick and would be harder for someone who really struggles with mobility.

Superhost

A staircase with white banisters and wooden steps leads to the upper level. The exposed antique brick wall provides historical character to the space. A woven area rug is positioned at the base of the stairs, complementing the warm wooden flooring.

Loft in Saint Charles

4.84 out of 5 average rating, 148 reviews

Main Street Historic Loft

DanielleRating, 5 stars1 month ago

This places was excellent. We enjoyed our stay. The place was cozy and comfortable, had what we needed. We were there on a Friday night…be warned it can get a little noisy outside so if that bothers you, then staying on a fairly busy street with lots of businesses probably isn’t for you. We weren’t bothered at all. Lots of great stores and restaurants on the same stretch of road. Definitely enjoyed our stay.

Top guest favorite

A modern kitchen is equipped with stainless steel appliances, including a gas stove and dishwasher. Open shelving showcases dishes, while a well-organized layout features several drawers. Natural light enters through small windows above the sink, and sleek countertops complete the space.

Home in South Hampton

5 out of 5 average rating, 40 reviews

Blair's Amazing House Sleeps 10 - 5 Beds - 2 Bath

JordanRating, 5 stars2 weeks ago

Matt’s listing was convenient driving to all that St Louis has to offer and walkable to several local restaurants, coffee, and park with brewery. We enjoyed the location very much. The house was as described and fit our needs for two families of 4 to stay. We enjoyed our stay.

Guest favorite

A fenced yard is featured, showcasing a blend of wooden panels in various tones. Flowering plants line the edge, with vibrant blooms among greenery. A putting green area is visible in the foreground, accompanied by a paved pathway leading to outdoor seating.

Home in St. Louis

4.89 out of 5 average rating, 207 reviews

Home away from Home St. Louis Cnty Ladue Schools

RaphaëlleRating, 5 stars2 weeks ago

Lisa was great! I needed a calm, peaceful and clean place for 2 weeks to recover from a surgery and her house was perfect. She was flexible with my arrival and departing time as I got updates from my surgeon and always worked it out with me, even last minute. There's a nice little park and neighborhood around and the house is very comfortable. Highly recommend!

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What guests are saying

Stay, Work & Play, 2bd w/office near Downtown

5 out of 5 average rating, 4 reviews1 month ago

This was a clean, quiet and modern apartment. We loved the themed decor, the 1904 World’s Fair. Very charming, and we had everything we needed. Clean, well appointed. Lots of accoutrements. Seemed recently rehabbed/remodeled. Parking space included, though we used the ample street parking. Centrally located. Near Botanic Gardens and Tower Grove Park. Easy to get to downtown or other neighborhoods. We would definitely stay again if the opportunity arises. 🏆

Apartment in St. Louis

What guests are saying

Historic Haven by JZ Vacation Rentals

4.81 out of 5 average rating, 43 reviews2 weeks ago

Situated in a beautiful neighborhood and offers excellent walkability to numerous wonderful attractions, stores, and restaurants. The space itself is very spacious and features a nice kitchen and bathrooms. Whether you're looking for a comfortable base to explore the area or a relaxing place to unwind between activities, this is a great choice.

Townhouse in Central West End

What guests are saying

Beautiful Family Retreat w/ Amazing Movie Theater

4.8 out of 5 average rating, 25 reviews1 month ago

We stayed at the house for about 7 months due to our house flooding. We were so thankful to have a house that was similar to ours in a location that was close. Brittany was great to work with! She was prompt with her replies and was flexible based on our ongoing change of schedule.

Home in St. Peters

What guests are saying

Chase's Cabin in The Sky

4.83 out of 5 average rating, 41 reviews3 weeks ago

I stayed at Chase's cabin in the sky for three nights. It was exactly what I was looking for! It felt just like home. The snack bar and all the small amenities really made the difference. I also got to see a red fox running along the river and two eagles flying around! I had my two dogs with me and it was the perfect hang out to chill and regenerate.

Cabin in Saint Charles

What guests are saying

Be in the heart of Mardi Gras - Across from Duke's

4.93 out of 5 average rating, 91 reviews2 weeks ago

This place was adorable! Stayed with 3 girlfriends for a concert downtown. We came back to the Airbnb and then walked to Mollys which was a lot of fun. Safe area, beautiful buildings, coffee nearby was excellent as well! Would totally stay again.

Apartment in Soulard

What guests are saying

Charming Cottage in Heart of New Town St. Charles

5 out of 5 average rating, 42 reviews5 months ago

I loved my stay at The Cottage! It was very clean, tastefully decorated, and smelled so nice as soon as I walked in the door. It was perfect for my stay in St Charles while attending a conference in the area. The area is beautiful and there is a great coffee shop nearby. Other restaurants and park areas are within walking distance as well. I highly recommend Lindsay's place and would love to stay there again!

Loft in Saint Charles

What guests are saying

Quaint and Cozy Hamlet

5 out of 5 average rating, 10 reviews2 weeks ago

My cousin was getting married and we needed a place to get ready. This house was PERFECT! Kevin was so incredibly nice letting us check in early and check out late to accommodate our wedding party. He went out of his way to make sure everything was exactly how we needed it. You don’t come by many people like that anymore! So blessed and thankful for Kevin and his generosity. Will definitely stay at this house again if I’m in the area!

Home in O'Fallon

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Popular amenities for Crestwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Crestwood's top sights

Grant's Farm133 locals recommend

The Magic House, St. Louis Children's Museum125 locals recommend

Dewey's Pizza21 locals recommend

Sam's Steakhouse12 locals recommend

Kirkwood Station11 locals recommend

Bar Louie11 locals recommend

Other great vacation rentals in Crestwood

Superhost

Home in Florissant

5 out of 5 average rating, 3 reviews

Florissant's Old Town Inn (3BR)

HelenRating, 5 stars8 months ago

What a treasure we stumbled across! If you enjoy the vibes of an older home this one is for you! The neighborhood is very safe and amazing! The actual home has glass door knobs (if you know you know). The antique ceiling lights are amazing. They do have electronic locks, which are easy to access. The baths are updated, as well as the kitchen. Everything you could need was provided. We rented the entire place, (upstairs and down). My husband and I enjoying a weekend to watch some Cardinals baseball with our two adult children and a granddog. Sitting on the back patio watching the Koi fish could not have been more relaxing. Thanks for a great adventure. I hope to be able to visit this home in the future.

Top guest favorite

A stylish bar area is presented with four black, cushioned stools set around a granite-topped counter. The backdrop features warm wooden paneling that complements the sleek black brick base, creating a modern yet cozy atmosphere.

Home in Ballwin

5 out of 5 average rating, 29 reviews

Perfect Getaway 3BR/3BA Home

JohnRating, 5 stars1 week ago

Another perfect stay at Perfect Getaway. The home was very clean and the host communication was quick and easy. Great neighborhood and great location. I highly recommend.

Superhost

An open living area features exposed brick walls and modern furnishings. A comfortable sofa is positioned beside a wooden coffee table, with a dining area nearby that includes a round table and chairs. Bright overhead lighting illuminates the space, enhancing the contemporary design.

Home in St. Louis

4.92 out of 5 average rating, 219 reviews

Private Oasis w/hot tub

JacobRating, 5 stars6 days ago

Mark's house was very nice and clean with a delicious hot tub

Guest favorite

The exterior of a tranquil retreat is framed by lush greenery and vibrant flower beds. A gravel path leads to the building, which features a sloped roof and large windows. The surrounding landscape includes various plants, contributing to the peaceful environment.

Cottage in Sugar Loaf Township

4.92 out of 5 average rating, 71 reviews

Cheerful one bedroom cottage on a horse farm

SavannahRating, 5 stars2 months ago

It was so nice to get away and relax for the night at the cottage! It was so peaceful! Water pressure in the shower was amazing and the bed was so comfortable! Will definitely stay again!

Guest favorite

An evening view captures a charming street scene, adorned with string lights that create a warm glow. The street is lined with decorative lamp posts, and a mix of buildings, including shops, adds character to the urban landscape, inviting exploration.

Home in Alton

4.85 out of 5 average rating, 102 reviews

Backyard Seclusion Cottage

ErikRating, 5 stars1 month ago

Second time staying here, love Susan as a host and the place is amazing! Thanks again for a great visit Susan!

Top guest favorite

The entrance features a set of double wooden doors framed by elegant columns and decorative planters. Lush greenery surrounds the steps, enhancing the inviting approach to the well-maintained exterior of the property.

Home in Tower Grove South

4.99 out of 5 average rating, 135 reviews

The Gateway Getaway

MoisesRating, 5 stars2 days ago

Everything was as described, the house is very spacious and our kids greatly enjoyed all the toys and books available — helped to keep them busy on a rainy day. Perfect location with short drive to downtown/main attractions but also a short walk to shops and restaurants

Guest favorite

Apartment in St. Louis

4.87 out of 5 average rating, 301 reviews

We do Italian STL style. Perfecto! Enjoy our NBHD!

AmyRating, 5 stars3 weeks ago

This was the perfect spot… peaceful, safe, and quiet neighborhood within walking distance of so many homey, welcoming local restaurants! It was lovely to be able to walk everywhere to dinner and not have to drive. And it was within easy driving distance of all the tourist stuff we wanted to do. The suite had everything we needed and we especially appreciated the labels on the light switches! Very clean and comfy. Would 100% stay here again.

Top guest favorite