Pet-friendly vacation rentals in Winter Park

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.

4.96 out of 5 average rating, 172 reviews

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

This spacious backyard features a uniquely-shaped pool surrounded by loungers and umbrellas, perfect for soaking up the sun. Lush greenery and palm trees provide a tropical retreat, while soft evening lighting adds to the serene atmosphere, making it an inviting spot for relaxation.

4.95 out of 5 average rating, 110 reviews

Private Pool Oasis w/Xbox, Fireplace, Projector

Discover Orlando from this beautifully remodeled home, perfectly located near Disney, Universal Studios, downtown, and prime shopping. Enjoy the serene private pool with stunning day and night lighting. The home features three stylish bedrooms with private TVs, two modern bathrooms, and a cozy fireplace with a dedicated seating area. Offering a blend of comfort and convenience, this home is your ideal base for an unforgettable Orlando experience. Book your stay to create unforgettable memories!

A tranquil backyard features a sparkling pool surrounded by lush greenery and palm trees. Sunlight reflects off the water, creating a serene atmosphere. A covered seating area adds to the comfort, enhancing the outdoor space that overlooks a picturesque view of Lake Gandy.

4.88 out of 5 average rating, 110 reviews

Recharging Lakeview Oasis w/Pool centrally located

Fall in love w/ our peaceful home w/ incredible backyard & pool overlooking Lake Gandy! Experience the tranquility of this safe, residential area. New furnishings for your comfort, cozy living room w/ an 85" Smart TV, comfortable bedrooms, laundry room & fully-equipped kitchen for a nice meal. Have fun at our spacious backyard, great for entertainment, bbq's & fire pit s’mores nights! Enjoy delicious organic fruit in the yard! Only 25min away from amusement parks & MCO! Superb for long stays!

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.

College Park/Winter Pk 1 bed/bath private entrance

255 sq ft studio- queen bed, workspace, kitchenette, large bathroom, private yard & entrance w/ easy checkin. This gem is clean & quiet w/ complete blackout in bedroom. Bathroom has tons of natural light & 3 shower heads. There’s an AC unit in the Airbnb, large TV w/Roku, microwave, fridge & Keurig. Comfy, peaceful at I-4 Par exit # 44. $30 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 Rollins College 1.9

4.92 out of 5 average rating, 374 reviews

4.93 out of 5 average rating, 273 reviews

Townhouse in Orlando

COMFY 2BR/2BA Escape — Pets Welcome FREE!

Cozy two bedroom, two bathrooms,with a fold out couch. Duplex unit w separate entrances. Close to Downtown and just minutes to all theme parks. Private entrance with keypad entry. Private patio with seating. Fully stocked kitchen. Private Washer/Dryer. Walking access to local bars, restaurants, groceries and entertainment. Disney, Universal, Orlando International Airport, Orange County Convention Center are all within a half-hour drive. Only an hour from the beach, Kennedy Space Ctr., etc.

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.

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, zip code 32804. 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 add the pet to the reservation.

4.97 out of 5 average rating, 335 reviews

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.

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.

4.91 out of 5 average rating, 198 reviews

4.95 out of 5 average rating, 187 reviews

A private pool area is surrounded by lush tropical landscaping, featuring tall palm trees and vibrant greenery. The sparkling blue water of the pool reflects the sky, while a paved pathway leads to the entrance. A serene atmosphere is created by the nearby plants and outdoor decor.

Home in Maitland

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

A living area is presented with a gray sectional sofa and a blue accent chair. The space is enhanced by a patterned area rug and a small coffee table made of wood. Light filters through window blinds, illuminating the room's cozy decor and shelves filled with books.

4.84 out of 5 average rating, 122 reviews

The Sunrise House

Welcome! Here we offer you a home that gives you access to all things Orlando. This cute bungalow has SO much to offer! Nestled in a quaint neighborhood, you can WALK to the local garden, charming markets, breweries, restaurants, and coffee shops of Audubon Park and Mills 50 District. If you want to explore further, Downtown Orlando and Historic Winter Park/Park Avenue are a short 5-minute drive away. Did we also mention that we are pet friendly? Bring your fur baby with you!

A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.

4.92 out of 5 average rating, 180 reviews

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Sept-April) ☞3 Bedroom 3 Full Bath W/extra 4th queen daybed ☞ Easy access to the 417 East West express way (toll rd.) to get around Orlando ☞Easy smart lock self Check-in ☞ Driveway Parking ☞ Luxury bedding ☞Smart TV's with Netflix in each room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

4.83 out of 5 average rating, 127 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.

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.

4.92 out of 5 average rating, 178 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

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.

4.96 out of 5 average rating, 184 reviews

Private pool home near Downtown

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.

4.95 out of 5 average rating, 173 reviews

Lake House Retreat w/ Firepit - Centrally Located

4.95 out of 5 average rating, 175 reviews

The image depicts a calm lake at sunset, with reflections of clouds and colors mirrored in the water. In the foreground, a fishing boat is anchored, positioned near the lake's serene shoreline surrounded by lush greenery.

Home in Longwood

Pvt Fishing lk , Pets,Nature, Pool,garage

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.

Elegant, Spacious Three Bedroom Residential House.

4.86 out of 5 average rating, 222 reviews

5.0 out of 5 average rating, 107 reviews

Home in Apopka

Lakefront Home•screened deck, dock•Long Stays OK

A spacious living area is displayed, featuring a sectional sofa and a large wall-mounted TV. The open kitchen showcases modern appliances and a dining table for six. Natural light floods the space through sliding glass doors that lead to the backyard.

4.95 out of 5 average rating, 194 reviews

Beautiful House Completely Remodeled

4.95 out of 5 average rating, 147 reviews

A serene lakeside view is presented, featuring calm waters reflecting a gradient of soft colors during sunset. A wooden dock extends into the water, framed by lush greenery and grasses. The landscape conveys a tranquil setting, inviting moments of reflection in nature.

Home in Winter Garden

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

4.99 out of 5 average rating, 135 reviews

A spacious bedroom features a large bed dressed in neutral tones, accented by decorative pillows. Natural light filters through angular windows, illuminating the space. A seating area with a gray bench is positioned at the foot of the bed, and wooden walls provide a warm backdrop.

Home in Longwood

Private 4-Bedroom home with pool!

Pet-friendly home rentals with a pool

4.78 out of 5 average rating, 390 reviews

An indoor swimming pool is showcased within a spacious area, illuminated by sunlight through large windows. The clear water reflects the blue ceiling beams, while natural stone accents line the poolside, creating a relaxed atmosphere. Comfortable lounge chairs are positioned nearby.

Guest suite in Maitland

Guesthouse w/Private Indoor Pool

4.93 out of 5 average rating, 417 reviews

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.

Guest suite in Orlando

Downtown Orlando Garden Retreat

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.

4.85 out of 5 average rating, 182 reviews

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

Home in Altamonte Springs

The pool area is enclosed with a protective screen, featuring a spacious heated pool surrounded by a wooden deck. A green umbrella provides shade over a small table and chairs, while a bright yellow building is visible in the background.

Tropical Pool/Spa Home-Disney-Theme Parks-Beaches

4.98 out of 5 average rating, 117 reviews

4.89 out of 5 average rating, 109 reviews

An outdoor area features a pool surrounded by lounge chairs and a sleek design. Soft lighting illuminates the space, creating a cozy ambiance. A sauna is visible, with a comfortable lounge area nearby, and a large screen mounted for entertainment.

Home in Longwood

Recharge @ Timberland Lodge: Pool Hottub Sauna

5.0 out of 5 average rating, 106 reviews

Home in Oak Ridge

Harmony | Heated Pool | 10 min Universal & Epic.

4.83 out of 5 average rating, 156 reviews

Condo in Orlando

Cozy space 5/10 universal & epic

4.93 out of 5 average rating, 147 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Private, pet-friendly home rentals

4.99 out of 5 average rating, 199 reviews

Guest suite in Orlando

Lakefront Hot Tub Retreat | Sunset View | Near UCF

4.91 out of 5 average rating, 33 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.

4.95 out of 5 average rating, 78 reviews

Top 1% Modern Japandi Retreat - Jacuzzi No Fee

A modern living area features a spacious sectional sofa, a round coffee table, and a dining table with high-backed chairs. Natural light fills the space, highlighting the open kitchen with stainless steel appliances and stylish pendant lighting.

4.91 out of 5 average rating, 43 reviews

Winter Park 3BR | Near Park Ave & Rollins | Pets

An open concept living area features a light grey sectional sofa facing a coffee table. Behind it, a sleek kitchen with modern cabinetry and an island is visible. Exposed wooden beams adorn the ceiling, and large windows provide natural light to the space.

5.0 out of 5 average rating, 42 reviews

Renovated Whole House Rental

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.

4.84 out of 5 average rating, 45 reviews

Cozy retreat - 8 min. to Park Ave / Pets welcome

A serene outdoor area features a sparkling pool surrounded by a paved patio. Two gazebos provide shaded seating options, complemented by a few lounge chairs and decorative planters. The fenced yard offers privacy, and the space invites relaxation and gatherings.

4.8 out of 5 average rating, 41 reviews

Casa Winter Park