Pet-friendly holiday rentals in Winter Park

4.94 out of 5 average rating, 212 reviews

A spacious sleeping area features a queen bed with a soft grey blanket. A television is mounted above a brick fireplace. Large windows allow natural light, offering views of the tropical backyard. A bistro table and chair set is positioned nearby.

Guest suite in Orlando

Cozy Orlando Studio • Private Entrance • Queen bed

Our 100% private studio retreat welcomes you with a plush queen-size bed and peaceful views of a lush, tropical backyard oasis. Enjoy thoughtful comforts including a full washer/dryer, bathroom with bidet, cozy brick fireplace, microwave, coffee maker, and mini fridge. Just steps from covered parking, your private street-facing entrance offers easy access. Water front restaurant only one traffic light away! The home is located 8 minutes to Downtown, 15 minutes to Universal and 30 minutes Disney!

4.97 out of 5 average rating, 143 reviews

A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.

Home in Lake Formosa

Spacious Home with Pool & Hot Tub near Downtown

Nestled in one of the most coveted neighborhoods near Downtown Orlando (Ivanhoe Village), you'll be within a 5-min walk to tons of restaurants, bars, breweries, and boutique shops. Boasting a heated pool, hot tub, tiki bar, patio area w/seating & two living areas -you'll have ample room to play, entertain or relax in your Tropical Oasis! ☀ Harry P. Leu Gardens – 4 mins ☀ Orlando Museum of Art – 4 mins ☀ Universal Studios – 19 mins ☀ Walt Disney World – 24 mins ☀ The Mall at Millenia – 16 mins

4.94 out of 5 average rating, 251 reviews

A spacious room showcases a comfortable bed dressed in quality linens, complemented by decorative pillows. Two bedside lamps provide soft illumination. A dining table for two is visible, alongside a mirrored accent wall that reflects the room's minimalist design and elegant decor.

Guest suite in Orlando

Mirror House

Soon as you enter our doors, you'll be enchanted by the blend of modern design with a homely atmosphere. It’s a single-room marvel that offers a comforting sanctuary. Immerse yourself in lines, tasteful furnishings, and a subtle color scheme that sets the stage for a stay. Modern amenities are at your fingertips.Sink into top-quality linens as you bask in the comfort of this space. We guarantee that you wake up feeling refreshed and prepared to embark on a brand new day filled with experiences.

Apartment in College Park

A cozy bedroom showcases a queen bed with an orange floral duvet cover and matching pillows. Three pieces of wall art in soft hues are displayed above the headboard. A door leading to the private entrance is visible, providing easy access.

4.93 out of 5 average rating, 290 reviews

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard area & entrance. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $20 pet fee No cleaning fee. Universal 11 mi Kia Center 3 mi Airports (MCO) (SFB) 23 mi Orlando City Soccer 4.6 AdventHealth Orlando 0.6 mi Orlando Health, Arnold/Winnie Palmer 3.8 Rollins College 1.9

Guesthouse in College Park

The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.

4.91 out of 5 average rating, 190 reviews

8th Green Cottage - A relaxing oasis in the city

The 8th Green Cottage is a relaxing oasis in the heart of Orlando. Located 5 minutes from downtown. Sitting on the historic 1924 Dubsdread golf course. Enjoy the great views, pleasant and quiet neighborhood all with easy access to everything Orlando has to offer. Location is key when traveling and the 8th Green Cottage delivers! Disney, Universal, and Sea World all within a straight shot down I4. Free play Arcade with 3500 games included in spare bedroom Pets are welcome and stay Free.

Guesthouse in College Park

A comfortable living area features a dark leather sofa, a wooden coffee table, and a dining table with chairs. Bright light filters in from the outdoor patio, revealing lush greenery and a seating area beyond the sliding glass doors adorned with a vibrant red umbrella.

4.96 out of 5 average rating, 464 reviews

The Coach House -2 bedroom/3 bath Orlando Getaway!

2 Bedroom/3 Bath House. Pet-friendly. Designed by renowned architect James Gamble Rogers II, the house is a 25-min drive ($23 Uber) from the MCO Airport. Nestled in the heart of Orlando's College Park district, it is an oasis just moments away from Downtown Orlando: nightlife, museums, and funky art and music scene. Take a 25-minute drive into Disney, Universal, or The Outlets. Uber/Lyft/Walk to nearby trendy restaurants, museums, theaters, boutique shopping, and our craft beer scenes.

Guest suite in College Park

A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.

4.97 out of 5 average rating, 262 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Guesthouse in Wadeview Park

A spacious bedroom features a large bed with white bedding and decorative pillows. Two soft bedside lamps illuminate the area, complemented by a cozy armchair and a decorative bench at the foot of the bed. Exposed brick wall accents the room.

4.98 out of 5 average rating, 122 reviews

The Cottage A Pet Friendly Guesthouse

Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.

Guest suite in Lake Underhill

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

4.93 out of 5 average rating, 395 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

4.84 out of 5 average rating, 113 reviews

A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.

Condo in Winter Park

Lovely Winter Park Home close to Hospitals !

Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

4.97 out of 5 average rating, 203 reviews

The pool area is illuminated at night, showcasing a crystal-clear water pool surrounded by comfortable lounge chairs. Vibrant bougainvillea lines the back wall, adding a pop of color to the tranquil setting. Soft lighting enhances the modern architecture of the adjacent building.

Apartment in Winter Park

Just 3 Blocks to Shops/Restaurants on Park Ave!

Modern, clean and unique. Fast internet speed: 263 MBPS download and 21.5 MBPS upload. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz countertops, high-end cabinetry and fixtures, great new furnishings and mattresses, 8' solid core interior doors, high ceilings, spacious open layout with a balcony offering fantastic sunset views and more! If you haven't explored Winter Park's Park Avenue, then you must!

An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.

4.91 out of 5 average rating, 151 reviews

Stunning Orlando Getaway w/Spa & Heated Pool

The whole group will enjoy easy access to everything from this centrally located Orlando location. This 1950s beautifully designed space has all modern amenities with an amazing outdoor living space. Located in College Park situated close to many amenities Orlando has to offer. Only 9 Minutes to downtown Orlando or 15 Minutes to Universal. The Acre & The Cottage Wedding venues are both within Walking Distance. Dubsdread is only 4 Minutes Away.

Popular amenities for Winter Park pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 174 reviews

Orlando Cactus House! 5min from Universal Studios

Home in Colonialtown South

4.98 out of 5 average rating, 256 reviews

Downtown Orlando Modern Zen Studio Private Hot Tub

Home in Altamonte Springs

A modern living room is presented, featuring a deep blue sectional sofa and a coordinating armchair. A circular glass coffee table sits at the center, complemented by a decorative vase with flowers. Natural light enters through a large window, enriching the neutral tones of the space.

4.87 out of 5 average rating, 199 reviews

Elegant, Spacious Three Bedroom Residential House.

A welcoming living area features two gray armchairs with decorative cushions, positioned near a round coffee table. A wall-mounted television displays a colorful image, while a fireplace and built-in shelves enhance the room's charm. Bright natural light filters in through the windows.

4.94 out of 5 average rating, 127 reviews

Updated Home* 2 King Bed Suites * Downtown Orlando

A spacious living area features a comfortable brown leather couch and a matching armchair, positioned on a colorful geometric area rug. A wooden coffee table sits in front, and a large flat-screen TV is mounted on the accent wall, complemented by a ceiling fan above.

4.9 out of 5 average rating, 196 reviews

SODO Mid Century Modern Cottage

4.94 out of 5 average rating, 118 reviews

Cheerful 3 bedroom with a spacious shaded yard

4.91 out of 5 average rating, 148 reviews

The open concept living area features a modern kitchen accessible from the lounge space. Bar seating for four is available at the kitchen peninsula. Colorful artwork adorns the walls, while natural light illuminates the room from numerous bright windows.

Home in Wadeview Park

SoDo Mid-Century Boho 2 BR w/Courtyard *Sleeps 6*

A spacious game room features a blue pool table at its center, surrounded by light wooden flooring. To one side, seating options include modern chairs and a couch, with natural light filtering through large windows. The kitchen and dining area are visible in the background.

4.94 out of 5 average rating, 139 reviews

Lake House Retreat w/ Firepit - Centrally Located

Pet-friendly home rentals with a pool

Superhost

A serene pool area is surrounded by lush landscaping and tall palm trees, with sunlight glistening on the clear water. The pool features a gentle curve, and a white fence encloses the backyard, providing privacy and a sense of tranquility.

4.86 out of 5 average rating, 159 reviews

3 BR/2BA Home w Private Pool~12 min to Airport!

4.97 out of 5 average rating, 473 reviews

Guest suite in Orlando

Sunny Heated Pool Suite • Prime Resort Area

4.85 out of 5 average rating, 116 reviews

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

Condo in Orlando

5 mins Universal 10 mins Epic park | Rustic LOFT

4.89 out of 5 average rating, 180 reviews

Apartment in Orlando

Apartment, 7 Min to Orlando Airport/ Lake Nona

4.89 out of 5 average rating, 127 reviews

A spacious living area features a large sectional couch and a stylish coffee table. Natural light filters through the windows, highlighting modern décor. An arcade game stands in the background, and a laundry area is visible to the left, contributing to the home's functionality.

Home in Casselberry

Cozy 4/2, King Beds, Pergola, Hot Tub & Pool

4.97 out of 5 average rating, 420 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal

4.94 out of 5 average rating, 157 reviews

A cozy living area features comfortable seating and a flat-screen TV, complemented by light streaming in through white blinds. A well-equipped kitchen is visible in the background, and an inviting bedroom with a king bed is seen alongside a detached private sauna, surrounded by lush greenery.

Cottage in Orlando

Mills Lakeside

Superhost

A spacious studio room features a king bed with decorative bedding and a leather sofa. Natural light filters through the sheer balcony curtains, and a wooden desk with a chair is positioned near the window. The warm-toned walls complement the patterned carpet.

Apartment in Orlando

4.79 out of 5 average rating, 415 reviews

Westgate Lakes+Spa Studio Sleeps 4

Private, pet-friendly home rentals

4.92 out of 5 average rating, 13 reviews

3BR House minutes walk to Park Ave and golf course

The living area showcases a spacious sectional sofa adorned with accent pillows, positioned near a sleek electric fireplace. A large Smart TV is mounted above the mantel. Light wood flooring complements the modern design, while a vibrant green accent wall enhances the atmosphere.

4.93 out of 5 average rating, 28 reviews

Spacious Modern Japandi Retreat - Winter Park

Guesthouse in Thornton Park

4.92 out of 5 average rating, 328 reviews

Charming Thornton Park Guesthouse

A spacious living area is presented with an inviting couch and a dark coffee table. A large television stands on a sleek media console. Natural light fills the room through glass doors leading to the outdoor space, with a dining area visible in the background.

4.91 out of 5 average rating, 33 reviews

Winter Park - Cozy retreat near Lake Killarney

The exterior of the home features a light green facade complemented by a stone pathway. Neatly arranged planters with greenery and colorful flowers add charm. A well-maintained lawn surrounds the house, with trees and landscaping visible in the background, contributing to a peaceful environment.

4.96 out of 5 average rating, 26 reviews

Magic City Escape

Guesthouse in College Park

A modern pool house is featured, with large glass doors opening to a swimming pool. The exterior includes a tree emblem and a small seating area with a chair. Sun loungers are positioned near the pool, surrounded by lush grass and a wooden fence.

4.98 out of 5 average rating, 97 reviews

Amazing New Pool House!

4.96 out of 5 average rating, 84 reviews

A wooden dock extends over calm waters, featuring a single lounge chair positioned for optimal lakefront views. The scene is framed by a bright blue sky, with fluffy white clouds reflecting on the tranquil surface of the water.

Home in Casselberry

Sunset Lake Retreat