Vacation rentals with outdoor seating in Leesburg

4.99 out of 5 average rating, 121 reviews

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

Getaway on the Waterway: Kayak, SUP, fish, relax!

Welcome to your peaceful Getaway on the Waterway right on the beautiful canal that connects Big and Little Lake Weir! Kick your feet up and wave at the boats going by as you grill or fish from the dock. Play a round of corn hole, hop on one of our paddleboards or kayaks for beautiful ride to either lake! Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, (they also offer sunset cruises and water taxi service to Eaton's Beach restaurant right from our dock!) RELAX and ENJOY!

Guesthouse in Silver Lake

The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.

4.98 out of 5 average rating, 425 reviews

Silver Lake Guest Pool House Very Private !

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

4.99 out of 5 average rating, 295 reviews

The tiny home is set amidst a lush forest backdrop, featuring a welcoming entrance that is framed by large windows. A spacious wooden deck is adorned with comfortable seating, including two bright blue chairs and two red chairs. A black hammock hangs between trees, inviting relaxation.

Campsite in Thonotosassa

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘tiny-house’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This brand new luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 1G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

The welcoming entrance of the home features a bright yellow façade with white trim and a covered porch. Two rocking chairs are situated on the porch, and brick steps lead up to the front door, framed by simple white columns.

4.96 out of 5 average rating, 183 reviews

Country Chic Cottage with Private Boat Parking

Beautifully remodeled historic home combines up-to-date amenities with charming southern style. 4 bedroom, 3 full bath home located in friendly Tavares, America’s Seaplane City. Only a half mile from downtown Tavares restaurants and shops, 10 minutes to Downtown Mount Dora, 15 minutes to Howey in the Hills and centralized between Lake Dora, Lake Eustis, and Lake Harris with lakeside activities, seaplane rides, boat rentals, and festivals. Less than an hour to Disney, Universal, and Sea World.

Guesthouse in Deer Island

A screened patio area is shown, featuring a private pool surrounded by an expansive deck. Comfortable seating arrangements are visible, along with lush plants and natural light streaming in from large windows overlooking the wooded landscape.

4.96 out of 5 average rating, 134 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

On 5 beautiful wooded acres with a boat dock on the canal. Relax by the shared pool, enjoy a BBQ by the firepit, fish from the boat dock, enjoy nature, or simply read a book in the gazebo. Sapphire Cottage has a Master with a queen size bed, a fully equipped kitchen, 2 full size sofa-beds, dinning area for 6, and a full size bathroom. Whether you are looking to relax, enjoy the farm animals, or a bit of adventure we have the perfect location. We live in the main house across the cottage.

4.97 out of 5 average rating, 194 reviews

A spacious wooden dock extends over the calm waters, surrounded by lush greenery. Several people are seated, enjoying a meal together. Lawn chairs are arranged comfortably, with trees reflecting off the clear surface of the water nearby, creating a serene atmosphere.

Home in Weirsdale

Beautiful House On the River, Kayaks, Large Dock!

Come relax by the river in this 3-bedroom, 2-bathroom vacation rental in Lady Lake, Florida. Recently built by our family in 2022, the home has a screened in back porch, a fire pit, WIFI, and is complete with a large private dock right on the Ocklawaha River. All that and it's located only 10 minutes from The Villages where you can shop and have fun. Centrally located 1-1/2 hours from Disney, Daytona beach, and Tampa. Lockbox key access is available for check-ins at any time of day.

4.91 out of 5 average rating, 116 reviews

A wooden dock extends into the calm waters, surrounded by lush greenery and mature trees. Steps lead up from the dock to a cottage nestled among the foliage, offering a serene and natural setting.

Cottage in Leesburg

Waterfront Cottage on The Harris Chain in Leesburg

Cozy waterfront cottage on Haynes Creek. Whether its relaxing, fishing from your own dock, boating the Harris chain, paddle boarding, birdwatching, use our kayaks or pedal boat, or exploring the nearby towns and springs... we have it all. Fully equip kitchen, outdoor grilling area, wifi and cable, parking, laundry, gas fire pit on your private deck, boat parking at your dock or book a tour with Monster Bass fishing. Walkable to nearby stores or Gator Bay for a drink, meal, or music!

Place to stay in The Villages

An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.

5 out of 5 average rating, 112 reviews

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

4.98 out of 5 average rating, 174 reviews

The exterior of the property features a fenced yard with shaded trees and a front lawn leading to a single-story house. A pool area with protective mesh surrounds the heated pool, illuminated with vibrant LED lights in evening settings. Indoor spaces exhibit an open layout with natural light and comfortable seating.

Home in Minneola

Spacious Getaway ~ Heated LED Pool & Ping Pong

Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $40 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

An open living area features a stylish blue sofa and a mustard-yellow couch, accompanied by a round coffee table. A dining set with teal chairs and a kitchen bar area are visible. Natural light enters through windows, highlighting the warm wood flooring.

4.77 out of 5 average rating, 114 reviews

Retreat with/full kitch/near pavilion/fenceyrd

Minutes from Tavares/Eustis Lakes Playground 🛝 in neighborhood 6 minutes from Downtown Mout Dora 6 minutes from Lake Pavillion Center 15min from via entertainment Pot, pan, and dinnerware Toaster, Blender available Grill available TV in all rooms This Gorgeous house is filled with board games, along with plenty of space to relax and spend quality times with loved ones. Pet Friendly** But please following proper instructions. please contact me and pay your pet fee

4.9 out of 5 average rating, 165 reviews

Home in Silver Lake

The Faith Estate - A Lakefront Storybook House

Welcome to The Faith Estate, a historic 5-bedroom, 3.5-bathroom lake house in Leesburg, FL, near The Villages, Eustis, and Mount Dora. Perfect for reunions, retreats, or a relaxing getaway. Ideal for boaters, with space for multiple boats and trailers—great for Harris Chain of Lakes events. The estate also allows approved events. Submit details via Airbnb for approval before check-in. Unapproved events are not permitted. Event setups must respect property guidelines.

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.

4.97 out of 5 average rating, 125 reviews

Lake Dora Dream-Waterfront/Pool

Luxurious lakefront home on Lake Dora - 8 minutes to downtown Mount Dora and Tavares. Enjoy your vacation in this newly renovated pool home (Pool Not Heated) on Lake Dora and the Harris chain of Lakes. Bring your boat or rent one nearby to explore the area by water and cruise the Dora Canal to Lake Eustis. Included is a guest apartment with private entrance totaling 4 bedrooms and 4 full baths. Just a half mile to the Tavares Pavilion and dining in downtown Tavares.

Popular amenities for Leesburg outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

5 out of 5 average rating, 6 reviews

Home in Wildwood

The Coconut Lounge 3/2 w/ Hot Tub & Pool Table

5 out of 5 average rating, 14 reviews

Begonia on the Bend – Stylish Home Near Sawgrass

A large outdoor pool is surrounded by a spacious deck, featuring neatly arranged lounge chairs. Palm trees are visible in the background, and a covered area with seating can be seen to the left. The sky features a mix of soft blue and wispy clouds.

5 out of 5 average rating, 12 reviews

2 min walk to pool, 4 seat cart, 5 min to Eastport

4.86 out of 5 average rating, 36 reviews

Villages - Priv. Htd. Pool 3BR/2BA, Conv. Location

A spacious living area features a sectional sofa arranged around a low wooden coffee table. A colorful accent chair adds a pop of color. Natural light streams through large windows, illuminating the light hardwood floor. A floor lamp and wall decor enhance the inviting atmosphere.

4.89 out of 5 average rating, 65 reviews

Your Home Away from Home in The Villages

4.97 out of 5 average rating, 92 reviews

Home in Mount Dora

Beautiful Mount Dora Charmer with Lake Ola Views

4.96 out of 5 average rating, 167 reviews

A covered outdoor deck features a colorful area rug with floral patterns, surrounded by two blue chairs and a small round table. The peaceful canal view is framed by lush greenery, with a dock visible in the background.

Home in Eustis

Summer on the water! Boating, Fishing, Tubing, Fun

A charming one-story house is set against a backdrop of large trees, with Spanish moss hanging gracefully. Features include a paved pathway leading to a small seating area with tables and chairs, surrounded by greenery. The nearby lake is visible in the distance.

5 out of 5 average rating, 10 reviews

The Golden Anchor

Apartment rentals with outdoor seating

4.8 out of 5 average rating, 51 reviews

A spacious bedroom showcases a large bed with a blue throw blanket and white linens. A modern lamp and a side table are positioned next to the bed. A vibrant blue accent wall complements the decor, while a large artwork piece hangs above the bed.

Apartment in Mount Dora

The Willow - The Estate at Mount Dora

4.93 out of 5 average rating, 110 reviews

An open living area features a modern design with a spacious layout. A comfortable sofa with accent pillows and a coffee table is set in front of a large window. The adjacent kitchen is equipped with sleek cabinetry and modern appliances, complemented by a dining space visible in the background.

Apartment in Kissimmee

3180-207 Resort Pool View Disney Universal Orlando

4.81 out of 5 average rating, 303 reviews

The bedroom features a spacious bed adorned with soft pillows and a textured throw blanket. Flanking nightstands hold stylish lamps, providing gentle lighting. A framed landscape image above the bed complements the neutral color scheme, and doorways to additional spaces are visible in the background.

Apartment in Clermont

Charming Lakefront Apt. Near Disney

5 out of 5 average rating, 61 reviews

A compact living area features a light-colored sofa with decorative pillows. A small dining table and two chairs are positioned nearby. The kitchen is equipped with cabinets and appliances, and warm lighting creates an inviting atmosphere.

Apartment in Leesburg

Downtown Leesburg Owners Suite

4.97 out of 5 average rating, 189 reviews

A living area features comfortable leather seating with red accent pillows and a coffee table. A wall-mounted television is positioned across from the seating. Two framed art pieces and green plants add decor to the neutral-colored walls and tiled flooring.

Apartment in Lakeland

Your Charming Place in Central Florida

Apartment in Ocala Historic District

The exterior of the Kemp House is showcased, featuring Tudor Revival architecture with distinct brick detailing and half-timbering. The structure is adorned with large windows and a well-kept front yard, highlighting the inviting entrance and surrounding greenery.

4.95 out of 5 average rating, 135 reviews

Historic second floor 3 bedroom apartment

4.94 out of 5 average rating, 105 reviews

A private sleeping area features a spacious bed adorned with floral bedding. Natural light enters through a window with blinds, illuminating the soft grey walls. A comfortable couch sits in the corner, while two lamps provide a gentle glow on bedside tables.

Apartment in Minneola

Private Cedar Hideaway

4.96 out of 5 average rating, 147 reviews

A living room is presented with green accent walls and hardwood flooring. A comfortable sofa with orange throw pillows faces two small coffee tables. Wall decorations include woven art pieces. A ceiling fan hangs above, and a door leads to a balcony, allowing natural light into the space.

Apartment in Kissimmee

Cozy 2Bed Boho Hideaway 10 Min to Parks Allows Pet

Condo rentals with outdoor seating

4.93 out of 5 average rating, 214 reviews

The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.

Condo in Citrus Ridge

Magical Stay Near Disney & ESPN

4.82 out of 5 average rating, 438 reviews

An aerial view of the property reveals a well-maintained swimming pool surrounded by lounge chairs. Palm trees are strategically placed around the pool area, providing shade. The building showcases a welcoming yellow exterior, and ample parking spaces are visible nearby.

Condo in Orlando

ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER

4.83 out of 5 average rating, 109 reviews

A contemporary living area features a gray sectional sofa and two blue armchairs. A wooden coffee table rests on a plush area rug. Art pieces adorn the wall above the sofa, and large glass doors open to a patio, allowing natural light to fill the space.

Condo in Kissimmee

Storey Lake Themed 3BR w/ Resort Pool- near Parks!

4.91 out of 5 average rating, 174 reviews

Condo in Orlando

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

4.92 out of 5 average rating, 145 reviews

The master bedroom features a spacious bed with a tufted headboard, complemented by a decorative mirror and framed artwork. Natural light streams in through a large window, revealing views of greenery. A warm color palette and wood accents create a relaxing atmosphere.

Condo in Citrus Ridge

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

4.92 out of 5 average rating, 191 reviews

A spacious heated swimming pool is surrounded by palm trees, offering a tropical atmosphere. Lounge chairs with umbrellas line the pool area, providing ample seating for relaxation. The pool's clear blue water reflects the blue sky, enhancing a calm and inviting environment.

Condo in Orlando

Spacious+LakeView 3b2b w/Pool&Shuttle to Parks!

4.86 out of 5 average rating, 111 reviews

A dining area features a round table set with white plates and glasses, complemented by woven placemats. A cozy seating area with a brown leather couch and decorative pillows is visible, alongside a large window offering natural light and views of the outdoor space.

Condo in Celebration

Private balcony, Disney under 10 mins, Roku+Cable