Vacation rentals in Longwood

Home in Altamonte Springs

The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.

Orlando Poolside Oasis

Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

4.95 out of 5 average rating, 112 reviews

4.9 out of 5 average rating, 299 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!!!

4.85 out of 5 average rating, 374 reviews

Two red kayaks are positioned on a tree trunk beside a peaceful lake, reflecting blue skies and lush greenery. A covered patio area is visible, alongside a hot tub, creating an inviting space for relaxation by the water.

Home in Lake Mary

Independent Unique Lake guest house/kayaks/jacuzzy

Independent Guest house with a beautiful lake where you can have unlimited kayaking use during your stay as option(2 kayaks). Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl, walking distance to windixie super market, downtown Lake Mary, dunking donuts , near Orlando Sanford International Airport. Walk to many restaurants and entertainment, 30 min to Daytona Beach. Near Wekiva springs. To go to Disney or Universal, we have easy access to I-4 and 4-17.

4.97 out of 5 average rating, 268 reviews

A screened wrap-around porch offers views of the lake, with sunlight casting striped shadows on the floor. Two lounge chairs are positioned for relaxation, while a colorful playpen is set against the railing. Decorative surfboards are mounted on the walls, enhancing the space's charm.

Cottage in Sanford

Lakefront,Sanford airport, Boombah, Venue 1902,UCF

The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.

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

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

4.98 out of 5 average rating, 120 reviews

4.98 out of 5 average rating, 144 reviews

A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.

Guesthouse in Longwood

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

5.0 out of 5 average rating, 48 reviews

Home in Apopka

Spacious Lake Home w/HotTub, Firepit, Grill, Games

Modern 3BR/2BA retreat designed for style, comfort & fun. Enjoy a huge living room with oversized couch & 105” 4K projector for movies or sports. Relax in the sunroom with workspace, sofa lounger & air mattress option. Game room offers pool, foosball, board games & more. Luxe bathrooms feature tile walls, floating vanities & spa-style tub/shower. Outdoors, unwind on the spacious deck, grill & dine by the firepit, or soak in the hot tub—perfect for groups seeking relaxation & entertainment.

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, 176 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

A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 133 reviews

Relaxing 3-Bedroom Pool Getaway

This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

4.91 out of 5 average rating, 149 reviews

A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.

Guesthouse in Lake Mary

Nature Unique lake view Tiny Guest studio

Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

Home in Altamonte Springs

A backyard swimming pool is surrounded by a natural landscape, featuring colorful floaties resting on the water's surface. Comfortable seating is arranged nearby, and palm trees provide a tropical touch to the serene outdoor setting, all under a softly lit evening sky.

Private Pool / Cozy Central Florida Home

Updated four-bedroom home in Altamonte Springs, ready for your stay! Perfect for groups. Plenty of free parking in the driveway and curb side. Only minutes from I-4, which means easy access to your favorite spots in and around Central Florida. Universal Studios, for example, is about 25 minutes away. SeaWorld is 30 and Disney Springs is about 35, depending on traffic. Plenty of sports complexes are nearby. Uptown Altamonte is just around the corner. No parties or events please.

4.87 out of 5 average rating, 142 reviews

4.96 out of 5 average rating, 84 reviews

A spacious living area features a comfortable sofa and armchair, with a decorative rug anchoring the space. A television is placed on a wooden stand opposite the seating. Natural light filters through large windows, enhancing the inviting atmosphere.

Home in Wekiwa Springs

Nob Hill-Comfort cozy home away from home Longwood

Located in the Lake Brantley Shores neighborhood of Longwood, this quaint and recently updated 3-bed/2-bath home is a welcome site for those wanting to relax and unwind in a cozy and comfortable setting. It’s truly a hidden gem that we call Nob Hill! Whether you’re working at a nearby office or venturing out the many theme parks and natural attractions of Central Florida, you’ll love the convenience of its location. Located minutes to Merrill Park and Wekiwa Springs State Park!

Popular amenities for Longwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Longwood

A bocce ball court is presented with a lush green playing area bordered by wooden planks. Colorful bocce balls are positioned at one end of the court. The surrounding features include a stone pathway and a wooden fence, providing an enclosed and inviting recreational space.

4.95 out of 5 average rating, 56 reviews

Central Florida Pool Home

Townhouse in Winter Springs

The Springs -Townhouse in the Winter Springs

4.94 out of 5 average rating, 51 reviews

4.84 out of 5 average rating, 63 reviews

2BR Home in Heart of Longwood

4.97 out of 5 average rating, 38 reviews

Home in Lake Mary

Casa Alma Vacation Home Steps from LM Event Center

The exterior of a single-story home is displayed, featuring a well-maintained lawn and a paved walkway leading to the entrance. Large windows flank the entrance, allowing natural light. Surrounding trees provide shade, enhancing the inviting curb appeal of the property.

4.97 out of 5 average rating, 37 reviews

WHEELCHAIR ACCESSIBLE 3 bedroom 2 bath family home

4.78 out of 5 average rating, 36 reviews

A spacious living area is adorned with rich wooden paneling and a high ceiling with exposed beams. A stone fireplace serves as a focal point, flanked by large windows allowing natural light. Comfortable grey sofas are positioned around rustic tables, enhancing the room's charm.

Home in Sorrento

Historic Hammock House

Superhost

A serene view of the lake is captured through large glass windows, displaying calm waters and natural greenery along the shoreline. The setting sun casts a warm glow on the landscape, highlighting the tranquil atmosphere. The indoor seating area, with woven chairs, offers a cozy vantage point.

5.0 out of 5 average rating, 6 reviews

Lakefront Home Where You Can Retreat and Relax