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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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.

Superhost

A spacious movie theater area features plush reclining sofas arranged for comfort, with a thick area rug underfoot. The walls are painted in a calming blue hue, and a projector is positioned for viewing. Additional seating options and soft lighting contribute to a cozy ambiance.

Home in St. Peters

4.81 out of 5 average rating, 26 reviews

Beautiful Family Retreat w/ Amazing Movie Theater

KendraRating, 5 stars2 months 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.

Guest favorite

A private heated pool is surrounded by a patio featuring lounge chairs and lush greenery. The pool's curvy shape is highlighted by a decorative brick border, creating a serene outdoor space for relaxation.

Home in Fenton

4.85 out of 5 average rating, 243 reviews

Fenton Oasis

LuisRating, 5 stars1 week ago

Debbie’s home was in absolutely spectacular condition! My son and I thoroughly enjoyed the pool, which was incredibly clean, just like the rest of the property. The neighborhood was very peaceful and quiet. Debbie’s communication throughout the entire stay was flawless — she even stopped by to personally make sure everything was perfect for us. I would highly recommend this place without a second thought. You will truly enjoy your stay!

Superhost

An outdoor patio area features two blue Adirondack chairs positioned on a wooden deck. The view includes a green lawn and surrounding trees, providing a sense of tranquility. A low fence adds definition to the space, enhancing its openness.

Apartment in Waterloo

4.78 out of 5 average rating, 69 reviews

Waterloo. 1 block from the downtown City Square.

MosesRating, 5 stars2 weeks ago

I've stayed here multiple times and it’s exactly as advertised: clean, peaceful, and comfortable. The apartment is well-stocked, the TVs are great, and having a washer/dryer in-unit is a huge bonus. It's a perfect spot if you're looking for a quiet place to relax near downtown Waterloo. Hosts are reliable and clearly care about making the stay easy and smooth. Highly recommend!

Vacation rentals for every style

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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 Farm54 locals recommend

The Magic House, St. Louis Children's Museum47 locals recommend

Kirkwood Station11 locals recommend

Victory Raceway St. Louis4 locals recommend

Billy G's Kirkwood4 locals recommend

CJ's Produce & Plants, East End of the Historical Kirkwood Farmers' Market6 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, 30 reviews

Perfect Getaway 3BR/3BA Home

BlakeRating, 5 stars1 week ago

Wonderful stay. The place was easy to access and exactly as described. The host was friendly and responsive. Would definitely stay again.

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, 224 reviews

Private Oasis w/hot tub

AndrewRating, 5 stars2 weeks ago

What a great stay! We felt right at home and enjoyed the privacy and peaceful surroundings. Thank you! I’d definitely rent here again.

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

4.84 out of 5 average rating, 103 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

An inviting lower-level living area is showcased, featuring a ping pong table at the center. Light wood flooring is complemented by a soft rug, while comfortable seating is visible in the background. Natural light streams in through a small window.

Home in O'Fallon

4.96 out of 5 average rating, 73 reviews

Peaceful, family 4bd/2bath home! Longer stay avail

EdwardRating, 5 stars4 days ago

the place was very clean and very quite surroundings

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 stars1 month 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