Pet-friendly holiday rentals in Longwood

4.95 out of 5 average rating, 125 reviews

A set of wooden steps leads up to a charming cottage nestled among trees. The entrance features large glass doors, inviting natural light into the space. The surrounding area is landscaped, enhancing the tranquil ambiance of the private property.

Cottage in Eustis

Redbird cottage and farm. Equestrian lake cottage

Step back into “Old Florida” charm at this updated 1968 lake cottage, on a 7-acre equestrian farm. Secluded from main roads yet just minutes from downtown Mount Dora and Eustis, this peaceful retreat offers the perfect blend of rustic serenity and comfort. Located on a lake that offers direct water access. Campfires are welcomed, and the tranquil setting is made even more magical by the sight of horses. Inside, you'll find cozy touches and comfortable furnishings, including pillow-top mattresses

4.95 out of 5 average rating, 225 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.

Guest suite in Altamonte Springs

A comfortable sitting area is visible, featuring a blue sofa with yellow accent pillows, a gray armchair, and a dark wood TV stand with a large flat-screen TV. Natural light filters through the large windows adorned with blinds, creating a bright and inviting space.

4.97 out of 5 average rating, 107 reviews

Private Studio King Bed & Massage Chair + Sofa

Quiet, peaceful & centrally-located private studio in Altamonte Springs. 1st floor, 2 private entrances, full kitchen, private AC, strong WiFi, free parking, and total privacy. Walk to Sandlando Park & Seminole Wekiva Trail. Just 2 blocks from I-4, 1.5 mi to Cranes Roost, Uptown & Altamonte Mall. Less than 10 min to Downtown Orlando, Wekiva Springs, hospitals & shopping. Ideal for remote work, extended stays, couples or solo travelers. Enjoy comfort, location & convenience. Book now and enjoy!

4.94 out of 5 average rating, 259 reviews

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.

Flat in College Park

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

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, 232 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.

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, 237 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.

Guest house 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, 115 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.

4.83 out of 5 average rating, 108 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, 121 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 Longwood pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 106 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

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

4.97 out of 5 average rating, 147 reviews

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.

Home in Orlando

Beautiful House Completely Remodeled

5 out of 5 average rating, 156 reviews

Home in Orlando

Orlando Cactus House! 5min from Universal Studios

4.88 out of 5 average rating, 113 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

4.91 out of 5 average rating, 161 reviews

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.

Home in Orlando

Modern Tropical House Heated Salt Pool

4.88 out of 5 average rating, 161 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

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

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 456 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 Resort Style - Pool & central location ☀️

4.97 out of 5 average rating, 198 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.

Flat in Winter Park

Just 3 Blocks to Shops/Restaurants on Park Ave!

4.99 out of 5 average rating, 143 reviews

A charming blue cottage is set within a lush green landscape, surrounded by a white privacy fence. Mature trees provide shade in the background, and a well-maintained pathway leads to the entrance, inviting exploration of the property.

Home in Mount Dora

Mount Dora, FL Private Corner Home w/pool

4.86 out of 5 average rating, 101 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.

Apartment in Orlando

5 mins Universal 10 mins Epic park | Rustic LOFT

4.97 out of 5 average rating, 400 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.

Apartment in Orlando

Waterfront Resort Condo near Disney &Universal

4.91 out of 5 average rating, 155 reviews

A spacious living area features a sectional sofa and a round coffee table, complemented by soft lighting. A television is placed on a low cabinet, while decorative plants and a wall art piece add visual interest. Natural light enters through a window, enhancing the inviting atmosphere.

Flat in Winter Garden

Stay A While

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

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.

4.92 out of 5 average rating, 385 reviews

Downtown Orlando Garden Retreat

Private, pet-friendly home rentals

4.89 out of 5 average rating, 36 reviews

The living area features a comfortable seating arrangement with a dark leather sofa and loveseat. A rustic coffee table is centered on a wood-style floor, while a stone fireplace adds warmth. Natural light enters through multiple windows adorned with blinds, enhancing the inviting space.

Apartment in Lake Mary

3/2 near beaches and theme parks

5 out of 5 average rating, 15 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

4.93 out of 5 average rating, 14 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.

4.85 out of 5 average rating, 48 reviews

The kitchen features modern cabinetry and a striking wall mural with geometric shapes and vibrant colors. A coffee maker and essential appliances are neatly arranged on the countertop. A dining chair is positioned at the small table against one wall, enhancing the space's functionality.

Flat in Sanford

Totally 80s!

5 out of 5 average rating, 4 reviews

A Key West style house is set within a lush landscape, featuring a spacious front porch and surrounded by greenery. The exterior displays soft pink siding, large windows, and a charming roofline. Tall palm trees and vibrant flowers contribute to the inviting atmosphere of the yard.

Home in Sanford

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

4.95 out of 5 average rating, 42 reviews

A modern kitchen features a large granite island with three upholstered stools. Sleek cabinetry and stainless-steel appliances complement the light grey walls and wood-like flooring. Natural light pours in through large windows, enhancing the spacious and functional layout.

Home in Sanford

4/3 Modern Farmhouse On 5 Acres Large Pond

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