Pet-friendly holiday rentals in Maitland

4.97 out of 5 average rating, 137 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

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.

4.94 out of 5 average rating, 271 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

4.93 out of 5 average rating, 151 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 | Downtown

This relaxing 1 bed 1 bath space in Downtown Orlando boasts a lush fenced-in private yard, hot tub, and fully equipped kitchen. We pride our studio on comfort, wellness, and delicate attention to detail to experience the magic of a trendy space in the heart of Orlando. Enjoy brand-new remodeling, furnishings, and appliances. This is the back unit of a 2-unit property. We include: ✅50" TV ✅Luxury mattress ✅Fiber optic Wi-Fi ✅Decaf Coffee & Tea ✅Disney Plus, Hulu, Max, Netflix ✅ Free Parking

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, 187 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.

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, 246 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, 178 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.

4.96 out of 5 average rating, 219 reviews

A contemporary living area features a large flat-screen TV mounted on a wall. A wooden console table sits beneath it, displaying decorative items. Two upholstered chairs provide seating, with a colorful area rug added for warmth. Natural light filters through window coverings.

Apartment in Winter Park

Apt C -Modern Elegance in the Heart of Winter Park

Light, bright and full of delight! Fastest internet speed available: 154MBPS download and 20 MBPS upload! Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Heated pool , poolside grill and bikes for your enjoyment! Three blocks to Park Ave and two blocks to the Winter Park Village! Simple elegance downtown defined by contemporary design and leisurely living. Enjoy the convenience and tranquility of one of Florida's best walking communities

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, 120 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, 388 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, 112 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.

4.9 out of 5 average rating, 146 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.

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.

4.81 out of 5 average rating, 103 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 Maitland pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 114 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

4.83 out of 5 average rating, 210 reviews

The spacious kitchen features a large island with a granite countertop, white cabinetry, and modern appliances. A comfortable seating area with two couches is visible in the background, complemented by wood flooring that enhances the home’s open layout.

Home in Lake Mary

RemodeledHouse w/king beds near Downtown Lake Mary

5 out of 5 average rating, 164 reviews

Orlando Cactus House! 5min from Universal Studios

4.97 out of 5 average rating, 116 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

Waterfront EPIC views, Dock, wildlife Near Disney

A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.

4.88 out of 5 average rating, 231 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

4.93 out of 5 average rating, 485 reviews

A spacious backyard is enclosed by wooden fencing, featuring a gazebo with seating and a clear space for outdoor activities. A pathway leads to a raised wooden platform. Sunlight casts shadows across the green lawn, enhancing the inviting outdoor setting.

Home in Clear Lake

Pet friendly house w/washer & dryer & AC & Parking

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.

4.93 out of 5 average rating, 122 reviews

Updated Home* 2 King Bed Suites * Downtown Orlando

4.88 out of 5 average rating, 111 reviews

A modern kitchen features sleek cabinetry and a large island with bar seating. Unique patterned ceiling tiles complement the granite countertops. A stainless steel refrigerator and double ovens are visible, highlighting a functional yet stylish cooking space.

Home in Lake Mary

Markham Woods 4BR Pool Retreat near Attractions

Pet-friendly home rentals with a pool

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.

4.86 out of 5 average rating, 108 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

4.89 out of 5 average rating, 174 reviews

Apartment in Orlando

Apartment, 7 Min to Orlando Airport/ Lake Nona

4.89 out of 5 average rating, 121 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

A bright bedroom is presented, featuring a spacious bed with crisp white linens and a decorative orange pillow. Soft overhead lighting highlights the warm tones of the wooden headboard. The room includes an ensuite bathroom, visible through an open door, enhancing accessibility.

4.91 out of 5 average rating, 393 reviews

Westgate Palace Resort 2 bedroom

4.87 out of 5 average rating, 119 reviews

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.

Home in Longwood

Tropical Oasis - Heated Luxury Pool - Game Room

4.98 out of 5 average rating, 120 reviews

A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.

Home in Kissimmee

Perfect Getaway. Private Pool.Kissimmee/Orlando

A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.

4.98 out of 5 average rating, 220 reviews

Lakefront Resort Condo near Disney and Universal

4.96 out of 5 average rating, 522 reviews

Guest suite in Orlando

Oasis comfy Suite #1 Location~Heated pool~4 Guests

Private, pet-friendly home rentals

The exterior of the bungalow is surrounded by lush greenery and colorful flowering plants. A manicured lawn leads to the front entrance, where a modern black door is framed by large windows. Tall trees provide additional shade and natural beauty.

4.85 out of 5 average rating, 39 reviews

Cozy Blue Bungalow

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, 69 reviews

Recharging Lakeview Oasis w/Pool centrally located

A modern living area is highlighted by large windows providing expansive views of the cityscape at sunset. A comfortable sectional sofa is positioned beside a dark accent wall, while a sleek pendant lamp hangs over a dining area, emphasizing the contemporary design.

5 out of 5 average rating, 4 reviews

The Blackstone® Luxury 1BR w/ King Bed, Gym, Pool

4.94 out of 5 average rating, 203 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

Private Guest unit W/Tropical Views!

5 out of 5 average rating, 71 reviews

Joe's Bar and Grill

4.85 out of 5 average rating, 165 reviews

A modern living area features a large sectional sofa and a glass coffee table. Natural light floods the space through multiple windows, enhancing the warm wooden flooring. A round dining table is set for four, while a decorative artwork piece adorns the wall.

Condo in South Eola

Beautiful Downtown Condo 1/1

An aerial view showcases the modern home with a welcoming gray and white facade. A golf cart sits on the paved driveway, ready for use. Lush greenery is present around the property, indicating a serene outdoor environment.

4.92 out of 5 average rating, 12 reviews

Golf Car Fun ,Spring & Swing Retreat

The pool area is shown with clear blue water reflecting sunlight, surrounded by lush palm trees. String lights hang above the pool, creating a vibrant outdoor atmosphere. A scenic view of the lake is visible in the background, enhancing the inviting environment.