Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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Guest favorite

A well-lit guest room features tall vaulted ceilings with exposed wooden beams and skylights. A cozy bed is adorned with patterned bedding, while decorative plants are placed around the space. Large windows allow natural light to fill the room, complemented by soft curtains.

Home in St. Louis

4.91 out of 5 average rating, 423 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.

Top guest favorite

The living room features a brown leather sofa with decorative yellow pillows and a coffee table with a rustic wooden top and slender metal legs. A cozy armchair is positioned nearby, accompanied by a soft throw blanket. Natural light illuminates the space through sheer curtains.

Home in Lindenwood Park

4.99 out of 5 average rating, 130 reviews

Near Forest Park, The Hill, WashU-Private Backyard

Backyard is private, large, fully fenced. Sitting area w/ solo stove & Adirondack chairs. Cleaned & maintained by host. Inside 1 bedroom you will find comfy king bed, queen sofa in living room. Modern amenities, fully stocked kitchen, & coffee bar. First floor laundry. Centrally-located, newly updated near The Hill & Forest Park. 1 min. from highway & no more than 10 mins from most everything STL-restaurants, downtown, hospitals, zoo, science center, coffee shops, stadiums & more! Dogs allowed!

Superhost

A vibrant backyard scene is captured, featuring a refreshing pool surrounded by lush greenery and colorful flower arrangements. Comfortable seating areas are arranged nearby, complemented by decorative umbrellas and a flag waving in the breeze, creating an inviting outdoor environment.

Home in Lindenwood Park

4.77 out of 5 average rating, 91 reviews

Heated Pool - Sprawling, Spacious, Family Friendly

The pool is open and guests are swimming! This pool is surrounded by gardens and entertainment areas. 2400 sqft of living space inside with multiple entertainment areas and rooms well spread out. This is the perfect house for multiple families or generations to enjoy together! The house is amenity packed and offers a stunning kitchen, as well as a vegetable garden for guests to use and save on groceries! Located in the perfect central location within 5-15 minutes of the cities main attractions!

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 St. Louis

4.93 out of 5 average rating, 285 reviews

Historic Victorian comfort, cold air

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

Guest favorite

A well-lit bedroom features a spacious bed with decorative pillows and a cozy blanket. Bamboo flooring complements the room's warm wood ceiling. A doorway leads to a private balcony with views of the surrounding landscape, creating an inviting space.

Guest suite in Affton

4.92 out of 5 average rating, 52 reviews

Anni's Attic

Anni’s Attic: A cozy, en suite with private balcony(overlooks our large backyard and boxwood lined patio, which guests can use), kitchennette, laundry, separate living area with gas fireplace and workspace including views of native landscape-all located 20 minutes from the best attractions. The gated entrance on the side leads to a lane filled with Midwest wildflowers, fruits and veggies-a favorite with pollinators in spring/summer and birds all year round. Custom paintings in space by host.

Top guest favorite

A view from the living area into the bedroom, showcasing a serene space with a queen-size bed dressed in crisp white linens and accented by earthy throw pillows. Natural light illuminates the room, complemented by a ceiling fan and light-toned wooden flooring.

Apartment in St. Louis

4.99 out of 5 average rating, 168 reviews

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

Top guest favorite

A light and airy living room is highlighted by a cozy white sofa adorned with various beige and cream throw pillows. A small side table holds a decorative tray with a plant and a soft throw blanket is draped over the arm of the sofa. Natural light enters through a nearby window.

Apartment in St. Louis

4.94 out of 5 average rating, 108 reviews

SALE! Charming Kirkwood (2) Bedroom

Welcome to this cozy home-away-from-home, designed with the Airbnb guest in mind! Minutes from downtown Kirkwood and 20 minutes from downtown STL it is perfect for those traveling for work or fun! Guests are provided internet, hotel linens, & laundry access. Settle in & enjoy cooking in the kitchen, relaxing in the living room, and resting in your hotel-inspired bedrooms. This listing was converted from a shared apartment to a full unit in August 2024. Prior reviews are for one bedroom.

Guest favorite

The exterior of a light blue Lustron home is featured, complemented by a vibrant yellow trim and front door. A large pink hippo sculpture stands prominently in the front yard, alongside green grass and white fencing, creating a playful and welcoming entry.

Home in St. Louis Hills

4.97 out of 5 average rating, 30 reviews

The HIPPO House! All 1950s Mini-Golf! MCM Lustron

Welcome to a unique 3-bedroom Lustron home in St. Louis, where retro charm and quirky details await! Greeted by Chelsea, our giant pink hippo, every guest steps into a rare mid-century gem—one of only 1,200 remaining Lustrons and even rarer with three bedrooms. Iconic steel walls, built-in cabinetry, and 1955 decor immerse you in history, while Wi-Fi ensures comfort. A backyard 9-hole mini-golf course adds some family fun. Book today to enjoy Chelsea’s welcome and a slice of history!

Guest favorite

A living area is featured with a modern sectional sofa positioned near large windows, allowing natural light to fill the space. A wooden dining table with chairs stands nearby, and a fireplace adds a cozy element to the room, complemented by a mirror and wall art.

Home in St. Louis

4.95 out of 5 average rating, 146 reviews

Cozy Fam Friendly Home-Large Fenced Yard & Deck

**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

Guest favorite

An entryway is shown with light-colored walls and a modern front door partially open. A decorative lamp with a beige shade sits atop a small, elegant table, which adds a welcoming touch to the space.

Home in St. Louis

4.95 out of 5 average rating, 39 reviews

2 Bedroom sleeps 6 in Affton w/ mobility ramp

Welcome to St. Louis County! This 2 bedroom, 1 bathroom house in Affton is newly renovated. New paint, new floors, new walls, new plumbing, new appliances, new kitchen that you will love. *Safe neighborhood *Kitchen - refrigerator, microwave, oven, dishwasher *Sleeps 6, 2 bedrooms with queen beds and 1 sofa bed *15 minutes from Downtown St. Louis *15 minutes from Grants Farm *15 minutes from South County Mall. *6 minutes from Walmart

Top guest favorite

A living room showcases a cozy seating arrangement featuring a light-colored sofa and a pair of armchairs. A round wooden coffee table sits centrally on a fluffy rug, while a stylish chandelier illuminates the space. The walls are adorned with floral accents, and large windows allow natural light.

Home in Tower Grove South

4.97 out of 5 average rating, 155 reviews

The Gateway Getaway Families | Near Park & Dining

Perfect for families or groups, this spacious 4-bedroom, 3.5-bath St. Louis home offers 6 comfy beds, 2 workspaces, and a chef’s kitchen. Kids can play in the fenced backyard while adults relax or cook together. Walk to Tower Grove Park, then explore South Grand’s amazing restaurants, bars, and shops just blocks away. Enjoy comfort, convenience, and local charm — all in one stylish home base for your St. Louis stay.

Top guest favorite

A modern red barn-style building features a gray roof and white trim. A large garage door is visible at the front, complemented by a set of external stairs leading to an upper level. Surrounding greenery is present, creating a serene environment.

Guesthouse in St. Louis

4.99 out of 5 average rating, 655 reviews

Cozy Barndominium Loft in Friendly Neighborhood

A modern, but cozy, 562-sq.-ft. loft apartment with full kitchen and bath, queen bed (with a Winkbeds Luxury Firm mattress)a twin Murphy Bed / desk, living room, walk-in closet, FireStick, Roku, DVD player, WiFi and more. Note that the barn is in our back yard and part of our home, so we don't allow instant book. We know it's a bit of a pain, but hope everyone will understand given that we live here too.