Vacation rentals with a pool in Longwood

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Top-rated rentals with a pool in Longwood

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious living room is featured with light-colored tile flooring. A large flat-screen television is mounted on the wall above a dark media console. One side includes a sleek sofa and a foldable futon, while a round coffee table is situated in the center.

Guest suite in Altamonte Springs

4.95 out of 5 average rating, 175 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Enjoy a stylish guest experience at this centrally-located Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

Top guest favorite

A private pool features a natural rock waterfall, surrounded by a paved patio. Lush greenery and trees provide shade, while a secure black fence encloses the area. Large windows of an adjacent building suggest inviting indoor spaces nearby, contributing to a tranquil outdoor setting.

Bungalow in Maitland

4.88 out of 5 average rating, 562 reviews

Maitland-Orlando Area, FL. Pool House Bungalow

Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Top guest favorite

A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.

Apartment in Altamonte Springs

4.96 out of 5 average rating, 326 reviews

St.John suite

Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

Guest favorite

Home in Lake Mary

4.88 out of 5 average rating, 99 reviews

Markham Woods 4BR Pool Retreat near Attractions

1 camera near the front door for security. Recording 24/7 Great blend of medieval charm and modern comforts in the spacious living area with expansive glass windows. Luxuriate in the lavish master suite boasting a king-sized bed and indulgent oversized showers. Outside, discover a sprawling backyard with a pool. **Please note: we charge a small event fee; discuss and pay before booking. ** Conveniently close to Disney, Daytona Beach, and local attractions for a serene getaway. getaway.

Top guest favorite

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.

Guest suite in Longwood

4.97 out of 5 average rating, 108 reviews

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

Share the backyard and NON Heated Pool with your hosts if we are home. Between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 31". We are not Handicap Certified but most wheelchair guests do not have issues. Grab bars in the bathroom.

Top guest favorite

A round above-ground pool is surrounded by a stone pathway and a grassy area. A blue shade sail is positioned overhead, offering protection from the sun. A swing set is located nearby, enhancing the outdoor recreational space.

Home in Longwood

4.96 out of 5 average rating, 137 reviews

Pvt Fishing lk , Pets,Nature, Pool,garage

No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes and kayak, 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 NEW SHOWS at DISNEY close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah

Guest favorite

A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.

Home in Maitland

4.86 out of 5 average rating, 123 reviews

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Guest favorite

A private, screened-in pool is visible, featuring a clear blue water surface and surrounding tiled edges. The pool area is enclosed, providing a tranquil atmosphere with natural light filtering into the space. A ladder is present for easy access to the water.

Home in Sanford

4.87 out of 5 average rating, 245 reviews

Private Pool at Flamingo Cottage

This 3 bedroom, 1.5 bath is equipped for a peaceful stay! At the intersection of 429, I-4 & SR417, under 40 miles from Disney & Parks, close to shopping & transportation, a screened private pool, a backyard, 2-car garage, cable, wi-fi, new appliances, fully equipped, renovated kitchen, a washer and dryer. Inside, tile floors keep allergens at bay. An older home set up to be comfy and homey. Vacation in a home setting! With outdoor seating and citrus trees, Florida is at your doorstep!

Top guest favorite

A serene pool area is surrounded by lush tropical plants and palm trees, providing a vibrant setting. A spacious pool is situated in the center, with a concrete deck and a charming thatched umbrella nearby. Comfortable outdoor seating is visible under a covered porch, enhancing relaxation.

Home in Maitland

4.95 out of 5 average rating, 167 reviews

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.

Guest favorite

Home in Casselberry

4.87 out of 5 average rating, 101 reviews

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 & Pool, it's great for both the adults and kiddos!

Guest favorite

A tranquil outdoor space features a private pool surrounded by light-colored stone tiles. Lush greenery and vibrant pink flowers add color to the scene. Multiple lounge chairs are positioned nearby, providing options for relaxation in a peaceful setting.

Apartment in Winter Park

4.96 out of 5 average rating, 214 reviews

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

Superhost

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

4.89 out of 5 average rating, 259 reviews

Gated community XL pool Home 2500sq/f

Our LK Mary home sits in Between the 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 quite nights for a full rest. NO BIKERS PLease! My home is in a Gated community.1 mile to Dtwn Lake Mary. Our pool is NOT heated, the hot tub only CAN be headed at an additional cost