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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Guest favorite
Home in Bevo Mill
4.9 out of 5 average rating, 477 reviews

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Guest favorite
A spacious living room features comfortable seating arrangements, complemented by a decorative area rug. Exposed brick accents are visible in the background, while additional dining space is accessible through an archway. Natural light fills the area from nearby windows.
Home in Lindenwood Park
4.86 out of 5 average rating, 812 reviews

Centrally Located Family Home - Park Like Yard

Cozy & charming home in super safe central location just 1-3 miles from the Zoo, Aquarium, Wash U, Forest Park, etc! Historic home with modern renovations! Thoughtfully decorated and designed for your comfort. Exceptional family amenities and full kitchen, BBQ. Stocked with family friendly amenities like pack and play, high chair, fold out cots, etc. Super safe area within walking distance to bars & restaurants. Easy on/off street parking. Secure garage & parking pad. New couches coming in fall!

Top guest favorite
A spacious living area features two comfortable sofas and an accent chair, arranged around a central coffee table. Soft lighting is provided by lamps beside the sofas. A large piece of artwork adorns one wall, and access to the kitchen and dining area is visible in the background.
Home in St. Louis
4.99 out of 5 average rating, 136 reviews

NO PARTIES, VERY QUIET NEIGHBORS. 3 BEDROOM 2 BATH

Two minutes from highways I270, I55, I44 which is within 15 minutes of downtown St. Louis. Busch Stadium, St Louis Blues, Zoo, Aquarium, Forest Park, Wash U, Soulard, Central West End, Missouri Botanical Garden, Anheuser-Busch. Other close attractions- Laumeier Sculpture Park, Children’s Magic House, Museum of Transportation, Grant's Farm. We are within one mile of Mercy South Hospital if you are working or visiting. MO Baptist, Mercy, BJC, Children's hospital all 15 minutes. 20 min/airport.

Top guest favorite
A comfortable living area features a gray sofa, patterned chairs, and a round coffee table on a natural fiber rug. Light streams through sheer curtains, highlighting the artwork of bicycles on the wall, creating a relaxed setting for guests.
Home in Kirkwood
4.97 out of 5 average rating, 244 reviews

A Kirkwood Cottage, Quaint Suburb of St Louis

Quaint cozy cottage on a “No Thru Street”. The best place to stay in Kirkwood.This was my childhood home. Only 1/2 mile to downtown Historic Kirkwood with its many shops & restaurants,Farmers Market, Kirkwood Park & Pool & Train Depot. A couple of miles to Museum of Transport,Powder Valley Nature Center & Magic House Museum is a MUST if you have children. Home has steps to entry & is 4th house from railroad tracks that are up on the hill at end of street.Close easy access to all major highways

Home in St. Louis
4.93 out of 5 average rating, 224 reviews

Velvet Gallery.

This home is a living gallery. Where modern design, art, and greenery breathe together. Every detail is curated to feel calm, intentional, and quietly inspiring. No stairs, no rush, just space to arrive. Evenings unfold on the private patio, lit by fire and soft glow, with a 50” smart TV and in-ground fire pit setting the mood. Nestled in a peaceful neighborhood just 10 minutes from downtown St. Louis. A place to rest, create, and let the world slow down. My personal home I created from love.

Top guest favorite
A log cabin with a dark metal roof is featured, accompanied by a covered porch area containing two chairs. Surrounding landscaping includes a well-maintained lawn and decorative stones, providing a natural setting that complements the cabin's rustic design.
Cabin in Pacific
4.99 out of 5 average rating, 134 reviews

Catch The Dream:; An Immersive Equestrian Escape

Welcome to the most serene and immersive equine retreat in the area! We are so happy you decided to stay with us. We want you to feel relaxed and at home as you enjoy the equine activities as well as the cozy log cabin and all its features and amenities! Enjoy views of the lush property and relax as you watch the horses graze and roam. We offer customized horsemanship opportunities that accommodate each person's level of comfort and ability. Cost: $75 for two hours, maximum of two lessons/day

Top guest favorite
A cozy living room is highlighted by a vintage-style mirror and decorative fireplace. Comfortable seating, including a golden armchair, is arranged around a central coffee table. Large windows allow natural light to flow in, complemented by patterned curtains and a detailed area rug.
Apartment in Southwest Garden
4.94 out of 5 average rating, 360 reviews

Historic Victorian comfort Great safe nghbhd

First, check out all 4 of our private 5 Star listings that creatively combines the old with the new. If one is unavailable, check the others by going to “My Profile” and scrolling down until you see all 4. This Historic building; built in 1896 has changed missions through the years; From church, to merc. Trade, to grocery store; quite the history have graced these walls. You’ll love our safe, Southwest Gardens area; next to the famous “Hill” offers unmatched restaurant, shops, bakeries

Superhost
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Fairview Heights
4.88 out of 5 average rating, 120 reviews

Wooded Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Top guest favorite
The exterior of a chalet is illuminated at night by warm string lights. Large windows reflect soft interior light, revealing a cozy atmosphere. The wooden deck is accessed by a railing, creating a welcoming entry. Trees are visible in the background, adding natural charm.
Home in Dittmer
4.96 out of 5 average rating, 587 reviews

Honeymoon Suite at Camp Skullbone In The Woods

Experience a romantic, quiet, and cozy chalet designed for two! This charming retreat features vintage décor and all the modern amenities you need for a comfortable stay. Unwind indoors by kicking back and watching a movie, surfing the web, curling up with a good book or a friendly board game, or sharing a drink with that special someone. In the evening, relax on the cozy deck under the stars, basking in the warm glow of the gas fire pit or unwinding in the inviting private hot tub!

Top guest favorite
Home in Rock Hill
4.95 out of 5 average rating, 177 reviews

Family Friendly Cozy Home w/ Lrg Fenced Yard

**FAMILY FRIENDLY** (See details for the items avail for families) This 2 bedroom home has everything you need for a relaxing trip! Fully updated with stylish and comfortable furniture and decor. Fully equipped kitchen and an amazing backyard/deck. Quiet street by one of the best Mexican restaurants in St. Louis - Hacienda - (can walk 2 min there) Close to everything! 13 minutes to the St. Louis Zoo 10 minutes to The Magic House 15 minutes to Busch Stadium & Union Station

Superhost
An inviting outdoor space is showcased, featuring a wooden deck with a dining area, lounge chairs, and a hot tub. String lights create a warm ambiance, while a fire pit adds a cozy element to the setting. The surrounding fence ensures privacy.
Bungalow in Carondelet
4.83 out of 5 average rating, 611 reviews

“HOT TUB” Oasis in the heart of the city!

Wonderfully renovated Bungalo in highly desirable Carondelet neighborhood. This home is surrounded by mini mansions on a very quiet safe street. 65” smart 4K tv, with Netflix and Hulu. high speed WiFi, and electric fireplace. There are two bedrooms one has a 12” gel king mattress bed the other has a full and a twin bunk bed style. All the furnishings are brand new! Inclosed porch to enjoy morning coffee. Large privacy fenced lot with hot tub and deck.

Guest favorite
A comfortable living room features a blue sofa, accompanied by a green chair and a wooden dining table. Natural light enters through a window with patterned drapes, illuminating the neutral walls and a decorative area rug. A wall clock and framed art complete the space.
Apartment in Lindenwood Park
4.87 out of 5 average rating, 228 reviews

Warriors Rest and Repose in St. Louis Hills

This first floor apartment is part of a 4-unit building on Jamieson. It is in St. Louis Hills neighborhood, a community with grocery and retail stores on the main drags – Chippewa and Hampton, with easy reach to city parks and the River Des Peres Greenway Trail. It is well-placed for all city visitors, here for excursions or family get-togethers, medical visits or business travelers, where visitors can rest and repose for another day of fun!

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