Pet-friendly holiday rentals in Overland Park

4.93 out of 5 average rating, 380 reviews

A spacious sleeping area features a queen-size bed dressed in soft linens and a blue sofa, along with a coffee table. A smart TV is mounted on the wall, and a desk is positioned in the adjacent office area, illuminated by natural light from nearby windows.

Home in Mission

The Little House: Cozy Home in Overland Park

- Adorable house on large lot (not a guest house/cottage) - 110 ft Driveway - Sleeping quarters with queen size bed (comfy memory foam mattress) - Living room with 40" smart TV, sofa-sleeper and additional seating - Fully equipped kitchen w/ eating area - Full bathroom w/ clawfoot tub/shower - Sunroom w/ seating area and daybed - Washer/dryer - Office area w/ desk - Deck w/ outdoor seating and grill - 10 min from the Plaza, 15 min from Westport and Downtown, 25 min from the airport - $25 pet fee

4.89 out of 5 average rating, 116 reviews

The exterior of the modern home features a striking façade with a mix of white cladding and natural wood accents. Expansive glass windows allow natural light to flow inside. A small outdoor seating area with wooden chairs complements the inviting entrance, surrounded by greenery.

Home in Westside North

Modern Madison - Near Downtown & Crossroads

Are you looking for a one-of-a-kind stay? Our property is like no other. Awarded by the prestigious American Institute of Architects and featured in various magazines, it's a modern, minimalistic and sustainable home. Everything is fully electric - powered by solar panels - reducing carbon footprint. It's located in the trendy Westside neighborhood, just steps away from Downtown & Crossroads. Make your stay a memorable one & enjoy the Modern Madison experience. Thank you for considering us!

4.88 out of 5 average rating, 198 reviews

A spacious entertainment area is highlighted by a large projection screen showcasing vibrant content. Modern wall sconces provide soft illumination, while a sleek glass table complements the contemporary sectional seating arranged thoughtfully to encourage relaxation.

Home in Prairie Village

Spacious Luxury Retreat w/ Hot Tub & Movie Theatre

Relax and take a break in this spacious family retreat! Check out the great outdoor space with 8-person hot tub, firepit and quite patio. Relax inside on the 12' sectional and watch your favorite movie on a 150" screen! Little kids will love swinging on the back yard playset, or climbing on the 25' pirate ship and two-story castle! Pool table in the game room is great for all ages! All bedrooms feature plush bedding and high quality mattresses and smart TVs. Full kitchen cutlery and utensils.

A cozy living area is highlighted by a large wall mural featuring trees and soft light. A sectional sofa and an armchair provide comfortable seating. A small coffee table sits on a patterned area rug, while a television and a work desk are positioned nearby.

4.94 out of 5 average rating, 534 reviews

Convenient Overland Park cottage on quiet street

Come relax in this 2 bed/2 bath cottage and enjoy the privacy of an 800 sq foot single family home. Master has queen bed and it's own private bath. 2nd bedroom has a queen bed. A queen size aerobed mattress is provided for extra sleeping room. Has a 50" flat screen TV equipped with Netflix/DVD player. Kitchen has granite counters and is fully stocked to make any great meal. Dining table seats 4 and kitchen seats another 3. Backyard with fire-pit. Pets welcome. Yard is only partially fenced.

A dining area is featured with a wooden table surrounded by four chairs. A colorful piece of wall art adds interest to the room. Opposite, a wooden sideboard displays dinnerware, while an open doorway leads to a comfortable living area with a sofa.

4.96 out of 5 average rating, 199 reviews

Glenwood Getaway - Great Location!

Experience the best of Overland Park from our charming, updated ranch. Nestled in a quiet neighborhood near downtown, this home allows you to experience the local lifestyle at its best. With two bedrooms, a modern bathroom and all the comforts of home, you will never want to leave! The interior blends cozy charm with contemporary amenities, while the secluded half-acre backyard is perfect for unwinding. Whether you’re here for a weekend escape or a longer stay, your perfect getaway awaits!

4.95 out of 5 average rating, 536 reviews

Home in South Hyde Park

The Lounge - Walk to KC Streetcar, Nelson & Plaza!

⛲ Stylishly updated bungalow in historic Midtown, minutes to Plaza & Downtown ⛲ Walkable to free Main Street Streetcar!! ⛲ Sleeps 4 with 1 king & 1 queen bedroom + ample storage & cozy finishes ⛲ Spacious living room w/ smart TV & desk + high-speed WiFi for work or play ⛲ Fully equipped kitchen w/ large island, dining for 6 & full coffee bar ⛲ Large bathroom w/ shower-tub combo, washer/dryer & luxury touches ⛲ Pet-friendly fenced backyard, back deck seating & free street parking out front

4.98 out of 5 average rating, 218 reviews

A living area features exposed brick walls complemented by wooden shelving. A dark leather sectional sofa is paired with a light-colored throw, while a contemporary coffee table occupies the center. Natural light filters in through large windows, illuminating potted plants.

Flat in Westside North

Historic, Industrial Flat in KC

Live the true Kansas-Citian lifestyle in this sparkling clean, and completely renovated 120-year-old brick beauty! Gorgeous hardwood floors, exposed brick walls, 10' island in the gorgeous chef's kitchen featuring gas cooktop and built-in oven/microwave. Spa-like bathroom with heated floors and rain shower head in the frameless glass shower. Spacious master bedroom with desk. Private rear deck and shared backyard. Walk minutes to KC's highlights: Crossroads, Street Car & Ferris Wheel!

Guest suite in West Plaza

The cozy studio features a spacious bed framed by white walls and rustic wood beams. A small dining table sits nearby, while a vibrant rug adds warmth to the concrete floor. Natural light floods in through large windows, complemented by decorative plants and wall art.

4.91 out of 5 average rating, 698 reviews

Backyard Artist Studio near Plaza

Backyard Artists Studio! *Pet Friendly* Walking distance to shopping and nightlife districts The Plaza and Westport. 200 sqft tiny living in a quiet backyard at the heart of Kansas City. Located close to everything KC has to offer. We are experts in all things Kansas City. This woodworking shop was turned into a cozy tiny home for artists. It boasts rustic exposed wood ceilings, a vintage kitchenette, patio deck, and comfortable mattress. Same day check-in time is after 6pm.

Holiday home in South Lake

A living area features a plush blue couch adorned with decorative pillows, complemented by a clear glass coffee table. A cozy chair with a light throw blanket sits nearby. Bright natural light filters through sheer curtains, enhancing the room's inviting ambiance.

4.91 out of 5 average rating, 153 reviews

Chic Modern Home in Downtown Overland Park

Chic modern stay in the heart of Downtown Overland Park! Relax with a plush king and queen bed, 1Gbps fast Wi-Fi, & washer/dryer. Walk to cafes, bars, shops, & the farmer’s market. Just 15 min to Plaza/downtown KC, 25 min to Arrowhead/MCI airport. Fully equipped kitchen & parking included. Perfect for couples or small groups (sleeps 4 w/ a queen air mattress available upon request). Book now for a comfy, convenient getaway that blends style & location—your ideal home base!

Guest suite in Overland Park

The exterior of the home is framed by lush greenery and colorful flowerbeds. A well-maintained lawn leads to the front entrance, where large windows provide ample natural light. An American flag waves gently from the porch, surrounded by trees offering shade.

4.93 out of 5 average rating, 142 reviews

Private DayLight Basement, Own Entrance, 1800 s/f

Spacious & beautiful 1800 sq ft apartment, sanitized, private entrance w/smart lock, Lg open floor plan, furnished kitchen - appliances, dishes, cookware, own Laundry, bath rm w/2 sinks, 55" smart HDTV, 2 queen beds, one private bedroom, one open bedroom with curtain surround, private lower level of home, Many sunny windows, cul de sac, many restaurants & shops, 2 min to hwy 69, Driveway parking. Pets welcome, Pet rules are under Booking Settings, then House Rules.

4.98 out of 5 average rating, 471 reviews

A cozy sleeping area features a spacious bed with striped bedding and layers of soft blankets. A dark upholstered bench with textured throws sits at the foot of the bed. A bedside lamp provides soft lighting, and a decorative cabinet stands nearby.

Guest suite in Olathe

Secret Garden Short Stay

1 King Bed. 1 Twin air mattress roll away (plz req rollaway) Washer/Dryer for your personal use. Fast Wi-Fi Fiber. Sep. fenced off backyard area with Private entry into your basement area that is located around the back of the main house. Parking space on property. Dog park, walking trails. Restaurants close by. Close to highwy, gas stations and shopping. We also have Solar panels that provide some back up for the heat/air and refrig if electricity goes out!!!

Guest suite in Overland Park

A modern studio space features a spacious queen bed with a patterned blanket and decorative throw. A compact kitchen area is visible with blue cabinetry. A small dining table with stools is present, along with a large area rug adding texture to the room.

4.98 out of 5 average rating, 232 reviews

Charming Basement Oasis

Pets- Dogs Only. Private basement suite with walk out entry, situated 1 mile from Historical Downtown Overland District. Within walking distance to South Lake Park. Basement suite is part of a single family home. The house is central air with thermostat located upstairs. Main level is occupied by residents & is separate from the basement suite. Suite includes full kitchen & laundry, full bathroom, walk in closet, one queen bed, & fold down sofa.

Popular amenities for Overland Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious living area features a large sectional sofa, complemented by a round coffee table. Natural light streams through multiple windows, enhancing the warm orange wall. A small desk is present, along with a decorative area rug that adds texture to the hardwood floor.

4.96 out of 5 average rating, 70 reviews

Beautiful guest house South Overland Park

4.79 out of 5 average rating, 128 reviews

A spacious living area is highlighted by a comfortable blue sofa adorned with yellow accent pillows. A light wood coffee table sits on a patterned rug, with a ceiling fan providing airflow. The kitchen area is visible, featuring modern appliances and a dining table.

Home in Grandview

Cozy House in Grandview

4.94 out of 5 average rating, 225 reviews

A comfortable living space is featured, showcasing a sectional sofa adorned with various textured cushions. A coffee table with a vintage trunk design sits on a patterned area rug. Natural light enters through large windows, complemented by dark curtains.

Home in Kansas City

Your home in KC!

4.97 out of 5 average rating, 186 reviews

The exterior of a charming single-family home is showcased, featuring a light-colored facade with decorative shutters. A front porch with steps leads to the entrance, surrounded by neatly landscaped greenery and small trees. The sidewalk is paved, and a wooden fence is partially visible in the background.

Home in West Plaza

Plaza Home walking distance to shops

4.93 out of 5 average rating, 152 reviews

A cozy living area showcases a sectional sofa and a matching ottoman on a patterned area rug. Natural light enters through large, partially shaded windows, enhancing the space. A flat-screen TV is positioned on a media console, providing entertainment options.

Home in Merriam

~Antioch Cozy Ranch~Pet Friendly~Central~Remodeled

4.81 out of 5 average rating, 160 reviews

A spacious interior features a high ceiling with exposed beams, enhanced by large windows allowing natural light. A dining area with several chairs surrounds a central table, while a sleek kitchen bar with stools is visible. Additional storage spaces are integrated along the wall.

Home in Shawnee

Royal Rabbit Charming Bungalow

4.91 out of 5 average rating, 173 reviews

A comfortable living area is showcased, featuring a leather sofa and two armchairs arranged around a round coffee table. Light hardwood floors complement a large area rug, while natural light enters through the windows. A full-length mirror adds depth to the space.

Home in Merriam

Cheerful 3 bedroom fully renovated cottage home

4.92 out of 5 average rating, 133 reviews

A cozy living area features a brown leather couch paired with a stylish side table and an eclectic floor lamp. A compact dining table with metal chairs is positioned near a large mirror, while natural light filters through the windows, enhancing the inviting space.

Home in Lee's Summit

Charming Mid-century Home DTLS

Pet-friendly home rentals with a pool

Home in Mission

4.75 out of 5 average rating, 4 reviews

Resort-Style Retreat w/ Pool | Prime OP Location

A serene outdoor space is showcased with a heated saltwater pool surrounded by smooth concrete and lush greenery. Two lounge chairs are positioned near the pool, while a cozy structure is visible in an adjacent area, offering a shaded retreat.

Home in Westside North

4.79 out of 5 average rating, 168 reviews

Amazing House with Heated Pool & Rooftop Hot Tub!

Flat in Rosedale

4.8 out of 5 average rating, 483 reviews

Relaxing 2BR Getaway Near KU Med with Pool | 18

4.95 out of 5 average rating, 62 reviews

A modern kitchen is presented with sleek appliances and ample counter space. Storage options include stylish baskets arranged on shelves. Light wood flooring complements the warm tones of the cabinetry. A well-lit pantry is accessible through double doors, enhancing functionality and organization.

Flat in Gladstone

Cozy 2-bedroom apartment in Kansas City North

4.74 out of 5 average rating, 109 reviews

A fenced backyard features a sparkling blue pool, inviting relaxation. The deck offers access to the house, with a smooth stone surface surrounding the pool. Lush greenery complements the outdoor space, enhancing the overall ambiance of the area.

Home in Olathe

Spacious & Updated Getaway! Pool & Hot Tub 10 Beds

5 out of 5 average rating, 36 reviews

A serene outdoor space features a heated pool surrounded by lush greenery. Comfortable lounge chairs are positioned under a shaded umbrella. The landscaped yard includes low shrubs and decorative stones, creating a relaxed atmosphere for leisure.

Home in Lenexa

World Cup Welcome Luxury in Lenexa w/hot tub

5 out of 5 average rating, 241 reviews

An aerial view reveals a shared outdoor pool surrounded by a concrete patio, adorned with lounge chairs and shaded areas. A charming guesthouse is visible nearby, complemented by a flagpole featuring an American flag, all set within a spacious green landscape.

Guest house in Shawnee

1 of a Kind Guesthouse on 4 Acres. Dogs allowed

4.9 out of 5 average rating, 49 reviews

A spacious backyard is featured, with a large above-ground swimming pool surrounded by a wood deck. Green grass covers the area, and trees provide shade. The home's rear is visible, with multiple windows and a porch leading to the pool area.

Home in Lee's Summit

Kelz-Cute & comfy. DTLS & KC Chiefs/World Cup

Private, pet-friendly home rentals

4.78 out of 5 average rating, 37 reviews

A welcoming living area features a cozy seating arrangement with a turquoise couch and two orange chairs. A lively green plant is positioned nearby, complementing the light wooden flooring. A television sits above a charming stone fireplace, with soft natural light filtering through the sheer curtains.

Home in Kansas City

Luxurious 2 Bedroom Kansas City Apartment

A spacious living room is depicted, featuring a large sectional sofa in a muted green tone and a wooden coffee table. Bright natural light enters through a nearby window, while a mounted television and decorative elements add to the room's comfort. A door leads to the exterior.

4.89 out of 5 average rating, 55 reviews

Spacious FamilyHome|GameRoom, 4 BR, Close KC Metro

4.9 out of 5 average rating, 10 reviews

The exterior of a three-story home is presented, featuring a light-colored facade and a welcoming orange front door. Surrounded by trees in a tranquil setting, stairs lead up to the entrance, and a pathway is visible, showcasing the landscaped front yard and neighboring houses.

Home in West Plaza

Stylish 2 bd Stay Near Plaza & UMKC

5 out of 5 average rating, 82 reviews

A cozy living area features two leather sofas adorned with decorative pillows and a coffee table. A warm lamp provides ambient light. A window offers natural light, with light curtains partially drawn. Decorative items are scattered on the table, enhancing a casual atmosphere.

Home in Olathe

Amazing Full Basement Apartment

4.92 out of 5 average rating, 39 reviews

The charming exterior of a single-story home features a welcoming front porch with a decorative bench. Lush greenery and potted plants enhance the landscaping. Large windows allow natural light to fill the interior, while the entrance is framed by a classic white trellis.

Home in Prairie Village

Peaceful and cozy home in popular Prairie Village

4.97 out of 5 average rating, 78 reviews

A bright living room features dark hardwood floors and comfortable seating arrangements, including two deep gray sofas and a round coffee table. Natural light filters through the blinds of a large window, while decorative plants add a touch of greenery to the space.

Home in Mission

Comfy Hideaway in Merriam

A relaxed living area showcases two sofas, one in light grey and the other in green, positioned around a wooden coffee table. A ceiling fan provides airflow, while a dining space can be seen in the background. Natural light complements the neutral color palette.

5 out of 5 average rating, 16 reviews

Great for Families|Sleeps 10|KingBeds|WiFi