Pet-friendly vacation rentals in Winter 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.

4.98 out of 5 average rating, 117 reviews

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

Your Tropical Paradise is ready and fully furnished from top to bottom! The Pool area has a hot tub. Near all attractions. Top of the line furnishings. Split plan--Master Bedroom is a king suite, pvt bathroom, 2 seperate bdrms on the other side of house. Heated pool/ hot tub has an small add'l fee Moments from I-4 & 20-25 minutes to Disney, Sea World, Universal, Famous Names discount malls, 35 minutes to Daytona & New Symerna Beach. Cranes Roost Park, Altamonte Uptown/Mall, 5 min

PetsWalkabilityWifi

A spacious living area is highlighted by exposed wooden beams above. A light-colored sofa is complemented by two bright orange chairs. A round coffee table is centered on a textured rug, while large windows provide natural light and views of the outdoors.

4.98 out of 5 average rating, 364 reviews

A Home Where Eclectic Luxury Meets Affordability

Welcome to The Altamonte House. Your home away from home. We offer free amenities, luxury bedding and pillows, and quintessential design throughout the home. There are work spaces in every bedroom, ultra-fast wifi, games galore, and a beautiful outdoor space equipped with outdoor dining and lounging. Events are allowed with fee. Pet Fee's per pet: $100 (notify host if you are bringing a pet-charged separately upon check in) Read the rules of the property before booking, to ensure that you agree.

Outdoor spacesWalkabilityLong stay

4.9 out of 5 average rating, 297 reviews

A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.

Home in Lake Mary

Gated community XL pool Home 2500sq/f

Need one night stay , reach out 4 special pricing. home rest between 2 most famous places central Florida has to offer, Disney World & Daytona beach and everything else in between. This property sits on 1/2acre of land, tropical landscaped backyard making your stay with us the true Floridian experience . Total privacy with quiet nights for a full rest. ! My home is in a Gated community.1 mile to Dtwn Lake Mary. POOL NOT heated, the hot tub only CAN be headed at an additional cost. NO TRAILERS!!!

Outdoor spacesQuietAccess

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, 142 reviews

Cozy King Studio • Massage Chair • Sleeps 4

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!

Outdoor spacesPetsDecor

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.

4.95 out of 5 average rating, 175 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

Outdoor spacesPetsView

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.

4.99 out of 5 average rating, 135 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! (Family visits are welcome 🤗) 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!

Outdoor spacesWalkabilityLong stay

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.

WalkabilityPetsIndoor spaces

4.88 out of 5 average rating, 156 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 in the heart of Casselberry/Orlando! Featuring 2 king beds, 1 queen, a bunk room (2 doubles & 2 twins), and an 8' farmhouse table seating 8, it's perfect for families and groups. Relax in the hot tub, cool off in the private above-ground pool, enjoy the Marvel Arcade, spacious walk-in shower, and patio with pergola, grill, and seating. Plus, a larger neighborhood pool & playground are just around the corner!

PetsOutdoor spacesDecor

4.86 out of 5 average rating, 251 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

Newly remodeled house located in beautiful Lake Mary, Florida. If the dates don't work for you, see our other nearby listing here: airbnb.com/h/gm-vacation-rentals-2 With the Central Florida theme parks, the surrounding restaurants, Florida's beautiful beaches, and dozens of other nearby attractions, you'll never run out of things to do. We look forward to being able to give you an amazing guest experience at our house.

WalkabilityPetsComfort

A contemporary house is framed by lush greenery, featuring a striking dark exterior with large windows. The front entrance is highlighted by a vibrant green door. A paved walkway leads to the entrance, complemented by a spacious lawn area.

4.95 out of 5 average rating, 115 reviews

Modern house with sauna and fenced yard

Come enjoy this uniquely stylish retreat for your next getaway! Our chic house blends comfort and contemporary design, creating a relaxing haven with sleek interiors and thoughtful touches. Unwind in the cozy living spaces or escape to the tranquil garden where you can relax in the sauna. Located in a quiet neighborhood, just a few blocks from Historic Venue 1902. Make your stay extraordinary in this one-of-a-kind oasis!

Outdoor spacesWalkabilityNearby

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.

4.86 out of 5 average rating, 222 reviews

Elegant, Spacious Three Bedroom Residential House.

Get the best experiences of Central Florida in this stylish, newly renovated centrally-located house. Minutes from top restaurants, beautiful Wekiva Springs and Rock Springs, Altamonte Mall, and Cranes Roost Area. Minutes from Super I-4 which can take you straight to downtown Orlando, Universal Studios, Walt Disney World. If you decide to go east enjoy beautiful downtown Daytona Beach, NASCAR, and New Smyrna Beach.

PetsOutdoor spacesLocation

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.

4.89 out of 5 average rating, 109 reviews

Recharge @ Timberland Lodge: Pool Hottub Sauna

Escape to Recharge @ Timberland Lodge — a bold, modern retreat in a quiet, mature neighborhood. This stylish home features sleek black ceilings, warm brass accents, a private pool, hot tub, sauna, firepit, and outdoor shower. At night, enjoy glowing outdoor lighting and total relaxation. Whether you're unwinding or celebrating, this space is made to impress. Book your recharge now!

Outdoor spacesPetsLayout

Popular amenities for Winter Springs pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

WalkabilityOutdoor spacesLaundry

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, 178 reviews

Modern Tropical House Heated Salt Pool

PetsWalkabilityValue

A spacious bedroom is shown, featuring a large bed with neutral bedding and pillows. Two bedside lamps provide soft lighting. A chair with a throw blanket sits in the corner beside a tall plant. Artwork hangs on the walls, and a window with sheer curtains allows natural light.

4.94 out of 5 average rating, 131 reviews

Bright & Airy in DowntownSanford

Outdoor spacesWalkabilitySleep quality

A modern living space is centered around a large gray sofa accented with bright orange pillows. A sleek wooden console holds a flat-screen TV, while a decorative plant and a small potted arrangement provide a touch of greenery. Large windows allow natural light to fill the room.

4.96 out of 5 average rating, 110 reviews

Cozy home in Orlando near UCF

Outdoor spacesPetsBreakfast

4.85 out of 5 average rating, 127 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 Heathrow

Markham Woods 4BR Pool Retreat near Attractions

Outdoor spacesPetsBiking

A historic home is nestled among lush greenery, with a wraparound porch and stairs leading to the entrance. Tropical plants and a wooden fence create a welcoming entrance. The large trees provide shade, enhancing a sense of tranquility in this charming neighborhood.

4.95 out of 5 average rating, 221 reviews

Historic Sanford Sunshine Cottage w/ Treetop suite

Outdoor spacesWalkabilityBiking

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

PetsWalkabilityLayout

A modern kitchen area is visible, featuring white cabinetry and a dark granite countertop. A large flat-screen TV is mounted above a fireplace, while a geometric design adorns the wall. Stainless steel appliances are included, providing a stylish and functional cooking space.

4.87 out of 5 average rating, 126 reviews

Renovated Peaceful Luxury Walk to Mall Park Publix

Outdoor spacesPetsKitchen

Pet-friendly home rentals with a pool

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, 109 reviews

Recharging Lakeview Oasis w/Pool centrally located

WalkabilityOutdoor spacesQuiet

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, 109 reviews

Private Pool Oasis w/Xbox, Fireplace, Projector

PetsOutdoor spacesParking

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, 177 reviews

Stunning Orlando Getaway w/Spa & Heated Pool

Outdoor spacesPetsWifi

4.93 out of 5 average rating, 147 reviews

Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Outdoor spacesPetsCleanliness

4.96 out of 5 average rating, 235 reviews

A modern living area features a sleek leather sofa with decorative pillows, complemented by a glass coffee table. The wall displays a large fishing-themed artwork. Neutral tones accentuate the space, and a dining area with high chairs is visible in the background.

Apartment in Winter Park

Apt D -Modern Elegance in the Heart of Winter Park

PetsOutdoor spacesWifi

4.97 out of 5 average rating, 159 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

Outdoor spacesPetsAccuracy

4.95 out of 5 average rating, 146 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

WalkabilityPetsLocation

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!

PetsWalkabilityShared spaces

Private, pet-friendly home rentals

4.88 out of 5 average rating, 443 reviews

Guesthouse in Maitland

Chez Bienvenu

PetsOutdoor spacesHospitality

4.99 out of 5 average rating, 198 reviews

Guest suite in Orlando

Lakefront Hot Tub Retreat | Sunset View | Near UCF

PetsOutdoor spacesAccess

4.98 out of 5 average rating, 63 reviews

Cozy, Clean 4BR Family Home Near Sanford Airport

Outdoor spacesPetsFamily

4.84 out of 5 average rating, 62 reviews

2BR Home in Heart of Longwood

PetsOutdoor spacesAmenities

The exterior of a single-family home is surrounded by lush greenery, featuring two prominent trees and tropical plants. A landscaped yard showcases a variety of colorful flowers along the path, complementing the warm tones of the house's facade.

4.93 out of 5 average rating, 95 reviews

Peaceful retreat family friendly home with parking

WalkabilityOutdoor spacesGetting around

4.95 out of 5 average rating, 77 reviews

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.

Home in Winter Park

Top 1% Modern Japandi Retreat - Jacuzzi No Fee

PetsWalkabilityBathroom

4.99 out of 5 average rating, 87 reviews

Guest suite in Sanford

The Studio atThe Bedford House-Sanford / 1BR&1BA

PetsOutdoor spacesTV