Pet-friendly holiday rentals in Winter Springs

4.98 out of 5 average rating, 208 reviews

A bright and airy bedroom is furnished with two spacious beds, each topped with coordinating grey bedding. A comfortable seating area is located in the background, and decorative plants create a calming atmosphere. Elegant wall art adds a touch of sophistication to the space.

Guest suite in Orlando

Bonsai House

Welcome to Bonsai Home, a unique blend of modern comfort and nature's embrace. Our charming abode, nestled between Orlando and Winter Park, offers a harmonious fusion of stylish interior design and a soothing ambiance. As you settle into your cozy living space, indulge in our thoughtful amenities and captivating details inspired by the tranquility of bonsai. Rest assured that we are at your service whenever you need assistance or have any inquiries. We extend our warmest welcome to Bonsai Home!

4.99 out of 5 average rating, 187 reviews

A cozy living area features a dark gray sofa and armchair, complemented by a light rug on the floor. A small desk with a chair sits against the wall, and a wall-mounted television is positioned above. Natural light pours in through the front door with a window.

Flat in Orlando

Parent's Retreat!

Whether working in the area, visiting your student or catching a UCF Sporting event. This pet friendly "Parent's Retreat" is just what you're looking for. Located less than 2 miles from campus. this apartment is a great place to land at the end of the day. Kitchen includes microwave, fridge, coffee maker and air fryer. This 380 sq ft newly remodeled mother-in-law suite has private entrance, patio and yard. Suite is completely closed off from the house and has keyless locks for easy check in.

4.89 out of 5 average rating, 114 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

Newly renovated farmhouse gem centrally located in the beautiful Casselberry / Orlando area. Stylish and thoughtful touches throughout will make you feel right at home. 2 king beds, 1 queen and 1 bunk room (2 doubles & 2 twins) along with an 8' farmhouse table (seats 8) makes this home great for both small & larger groups alike. Complete with a hot tub, amazing walk-in shower, Marvel Arcade, Private patio with pergola outdoor furniture & gas grill, it's great for both the adults and kiddos!

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.

4.94 out of 5 average rating, 145 reviews

Pvt Fishing lk , Pets,Nature, Pool,garage

No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

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, 238 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.

4.95 out of 5 average rating, 176 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.

The bedroom is equipped with a spacious wooden bed and a light-colored quilt. Two bedside tables with lamps are placed on either side. A ceiling fan provides air circulation, and a large window allows natural light to enter, complemented by white curtains. A chair is situated near the TV.

4.79 out of 5 average rating, 120 reviews

Cozy Getaway | Game Garage + Fenced Backyard +more

Unwind in a comfortable and well-equipped home! Play pool, fusball, darts, and basketball in the game garage. Conveniently located near Orlando/Sanford Airport, Wekiwa Springs, and a variety of attractions. Enjoy the fully equipped kitchen for all your culinary needs, sleep soundly in comfortable beds, and relax on the spacious back deck with a privacy fence. We have an old school Nintendo 64 and retro Galaga game on the wall to play. Perfect for work, family, or vacation getaway!

A modern kitchen features white cabinets and stainless steel appliances, complemented by granite countertops. A large island with seating is positioned centrally, while the dining area is visible through glass doors leading to the backyard.

4.93 out of 5 average rating, 239 reviews

Cozy 3 Bedroom Home, Great location!!

Equipped with one camera near the keypad facing the front door and is recording 24/7 , and perfectly situated in an ideal location. The marble countertops and stainless steel appliances create a dreamlike setting. The fenced backyard features a barbecue grill, smart TVs, and board games. Note: we charge an event fee; do not book without discussing and paying the fee. Minutes from I-4, Wekiwa Springs State Park, Disney, and Downtown Orlando. Book this exquisite sanctuary today.

Home in Altamonte Springs

A spacious living area features a large leather sectional sofa facing a stone fireplace. Natural light floods the room through skylights and glass doors that lead to the screened-in pool. An adjacent dining area is visible, showcasing a wooden table with chairs.

4.82 out of 5 average rating, 134 reviews

Quiet Place, convenient to everything!

Spacious home in a very quiet residential neighborhood. Perfect home away from home for your special getaway. Vacations, business trips, wedding groups, graduations have all been hosted in the past, and everyone had a great time. There's significant value in having your own quiet place and multiple rooms in a family-friendly setting. DO NOT BOOK MY QUIET PLACE IF YOUR PLAN INCLUDES ANY LARGE GATHERING WHICH MIGHT IMPACT MY HOME OR NEIGHBORHOOD. YOUR RESPECT IS EXPECTED.

4.83 out of 5 average rating, 109 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.

Apartment 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.

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.

4.98 out of 5 average rating, 122 reviews

Private 4-Bedroom home with pool!

Entire home located on 1 acre of land in the luxury neighbor hood of Markham Woods. This property is the ideal place to stay for a family vacation, or business trip. Take a swim in our large pool and enjoy the Florida Sun! Please add exact number of your guests, in your booking! Please NO Parties or gatherings! Please NO smoking on the property. If any violation occurs, your stay will be terminated immediately, and you will be charged a $1,500 fine!

Villa in Altamonte Springs

A modern kitchen is equipped with stainless steel appliances, including a refrigerator, oven, and dishwasher. White cabinetry contrasts with the light-colored backsplash and countertops. A window provides natural light, while a coffee maker and various kitchen utensils are arranged on the counter.

4.8 out of 5 average rating, 102 reviews

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

-Studio Style Unit, Renovated cozy peaceful home with convenience of walkout patio & nature to a walking distance for the mall, park, & Publix - Studio Style Unit, Perfect location yet secluded from the hustle and bustle of Orlando and surrounding areas. - Close to Orlando attractions, lots of stores and uptown Altamonte springs but still nestled in a quiet and peaceful area. - Plenty of parking right in front of the property

Popular amenities for Winter Springs pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 107 reviews

An open-concept living area features natural light streaming through large windows with scenic views of the lake. Cozy seating arrangements include a comfortable sectional and accent chairs, complemented by a dining space and a well-equipped kitchen with modern appliances.

Home in Tavares

Lake Dora Dream-Waterfront/Pool

5 out of 5 average rating, 9 reviews

A refreshing pool is surrounded by a stone patio, featuring a spa and tiled accents. Sunlight creates a shimmering pattern on the water's surface, while shadows from trees add depth to the serene outdoor setting.

Home in Winter Park

Gem Vacation Winter Park

4.93 out of 5 average rating, 147 reviews

The cozy sleeping area features a spacious bed adorned with luxurious cotton sheets and coordinating pillows. A rattan headboard complements the tropical-themed wallpaper. A small seating area with a brown couch and decorative pillows is visible, adding to the inviting atmosphere.

Home in College Park

The Boho Jungalow - Private | HotTub I Downtown

4.95 out of 5 average rating, 108 reviews

The inviting living room features a light-colored sofa flanked by two dark gray armchairs. A round coffee table is centrally placed, surrounded by a textured area rug. Natural light is provided by large windows, enhancing the room's spacious feel.

Home in Deltona

Stunning home with screened patio & fenced yard

Home in Colonialtown South

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.

4.97 out of 5 average rating, 156 reviews

Private pool home near Downtown

4.81 out of 5 average rating, 27 reviews

The entrance area is shown, featuring a welcoming front door framed by two lantern-style lights. A pumpkin sits on the ground next to a small garden bed with plants. A mat lies in front of the door, creating a cozy entryway.

Home in Winter Park

New built Private Studio Orlando/Winter Park area

The exterior of the house is showcased, illuminated by soft lighting. Lush palm trees are positioned nearby, enhancing the tropical atmosphere. A spacious patio area is seen, featuring a custom in-ground pool surrounded by comfortable lounge furniture, ideal for relaxation.

4.87 out of 5 average rating, 118 reviews

Tropical Oasis - Heated Luxury Pool - Game Room

4.97 out of 5 average rating, 130 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

Pet-friendly home rentals with a pool

4.86 out of 5 average rating, 147 reviews

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.

Home in Orlando

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

4.93 out of 5 average rating, 15 reviews

A serene lakeside view features a calm body of water reflecting the sky. Three tall trees are visible on the grassy banks, with the surrounding greenery creating a natural environment. The image is framed by a staircase leading down towards the lake.

Flat in Lake Mary

Entire Condo with Water View.

4.98 out of 5 average rating, 458 reviews

A fenced oasis-style backyard features a heated in-ground pool surrounded by lounge chairs and tropical plants. A sunshade provides comfort over the pool area, while an outdoor seating area with a gazebo can be seen in the background beneath the bright blue sky.

Guest suite in Orlando

Sunny Heated Pool Suite • Prime Resort Area

4.88 out of 5 average rating, 168 reviews

Flat in Orlando

Apartment, 7 Min to Orlando Airport/ Lake Nona

4.89 out of 5 average rating, 79 reviews

Home in Casselberry

Moxy Luxe Vacation / Heated Pool/ King Bed Ste

4.95 out of 5 average rating, 107 reviews

A comfortable living area features a sectional sofa adorned with cushions in shades of yellow, teal, and deep purple. Two small tables sit in front, accompanied by a patterned area rug, while decorative wall art adds visual interest. Natural light filters through a window with blinds.

Flat in Bay Lake

Charming Oasis 10 Min to Parks Pets Allowed

4.88 out of 5 average rating, 162 reviews

The exterior of a two-story Spanish Mission-style home is depicted in soft twilight. The structure features arched entryways with large windows, surrounded by lush landscaping. A decorative lantern illuminates the front entrance, enhancing the inviting charm of the property.

Home in Lake Cherokee

3,000 Sqft Historic Home With Pool Near Everything

Guest house in Southern Oaks

A bright living area is presented with vaulted ceilings and hardwood floors. Comfortable seating is arranged around a central coffee table, with soft lighting provided by table lamps. Natural light filters through the windows, illuminating the decor and creating a welcoming atmosphere.

4.84 out of 5 average rating, 109 reviews

Historic lakefront guesthouse

Private, pet-friendly home rentals

5 out of 5 average rating, 16 reviews

An open-plan studio layout is displayed, featuring a full kitchen with stainless steel appliances, a dining area with a small table, and a comfortable living space with a dark sofa. A spacious bed is positioned against the far wall, with ample natural light streaming in from multiple windows.

Flat in Apopka

Comfy Farm Studio Stay

5 out of 5 average rating, 4 reviews

The exterior of the home features a pastel pink siding, complemented by white trim and a classic porch with railings. Tropical plants, including a palm tree, are visible in the yard. The roof is topped with a weather vane, adding to the charming design.

Home in Sanford

Home in Sanford Countryside 3 Bed/2 1/2 Bath

4.92 out of 5 average rating, 26 reviews

A bright, open living area is furnished with a deep blue sofa and two woven chairs. A wooden coffee table sits in the center, surrounded by decorative elements. Large windows provide views of the lush greenery outside, while a wall-mounted television complements the space.

Home in St. Cloud

2 BR Lake View off-grid Home

5 out of 5 average rating, 8 reviews

The living room features a high, sloped ceiling with skylights, allowing natural light to fill the space. A light-colored sectional sofa is paired with gold-accented side tables. A piano sits in a corner, with a decorative fireplace and a television mounted above it.

Home in Maitland

Casa Feliz

4.98 out of 5 average rating, 40 reviews

An outdoor area is enclosed by a gazebo, featuring a charcoal-colored sofa and an orange inflatable hot tub. A hammock is suspended nearby, while yellow lounge chairs are positioned along a grassy lawn, creating a relaxing space for leisure and enjoyment.

Home in Orlando

Jacuzzi+GameRoom by Downtown/UCF

4.97 out of 5 average rating, 29 reviews

An outdoor area features a paved surface with a blend of grey and black tiles. A welcoming sign hangs on a white fence, which encloses the space. Potted plants add greenery, including a tall palm and another succulent, enhancing the relaxing environment.

Guest house in Orlando

The Cozy Corner

4.82 out of 5 average rating, 11 reviews

A living area features a comfortable gray sofa and a dark sofa set against light-colored walls. A small black table sits in front, displaying minimal decor. A mounted television is positioned above a wooden shelf, and natural light filters through white shuttered windows.

Loft in Oviedo

New Cozy Apartment Studio