Holiday rentals with a pool in Tavares

A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

4.96 out of 5 average rating, 141 reviews

2/2 custom pool home with 4 person gas golf cart

Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

4.94 out of 5 average rating, 112 reviews

Tiny home in Clermont

Tiny Hamptons | No Pet Fees | Main Floor Bed

A Masterclass in Luxury Tiny Living Welcome to the "Bridgehampton"— model by Tiny Hamptons LLC. As professional luxury tiny home builders, we designed this space to prove that downsizing doesn't mean compromising. Unlike standard DIY rentals, this home features master-grade craftsmanship, from custom cabinetry to premium quartz finishes. Whether you're here for a 'test drive' before building your own or just a high-end Clermont getaway, you’re staying in a professionally engineered work of art.

4.96 out of 5 average rating, 339 reviews

A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

Home in Lady Lake

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

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

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, 136 reviews

Sapphire Cottage - sleeps 6, on 5 acres with canal

Escape to Sapphire Cottage, a 5-acre wooded retreat with a private canal boat dock. Relax by the shared pool, fish from the dock, or enjoy a BBQ at the firepit. Our cozy cottage features a queen master, 2 sofa-beds, a full kitchen, and dining for 6. From meeting our farm animals, biking, kayaking, or reading in the gazebo, there is something for everyone! We live in the main house across the way and are happy to help while ensuring you have a peaceful stay. Come make lasting memories with us!

4.96 out of 5 average rating, 377 reviews

A bright outdoor lounge area is furnished with comfortable wicker sofas, set against a backdrop of large windows overlooking a shared saltwater pool. A colorful area rug adds vibrancy, while a ceiling fan circulates air within the space.

Guest suite in Lake Mary

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized jetted tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

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, 114 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!

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 103 reviews

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

4.97 out of 5 average rating, 129 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

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.

4.98 out of 5 average rating, 198 reviews

A charming yellow cottage with a metal roof is docked at the marina. A covered front porch features blue chairs and offers a view of the water. An American flag waves gently, while a sign indicates a private dock. Lush greenery surrounds the area.

Houseboat in Sanford

Enjoy the Magic - Floating Cottage on the River

Welcome to FLOATING COTTAGE . . . Imagine staying in a small cottage, gently afloat on the beautiful St. Johns River in Sanford, Florida. Perfect for social distancing! Sanitized between guests. Contactless check-in. Floating Cottage provides a magical space to relax, refresh and explore. Relax on the front porch; enjoy the warm breeze while watching marina activity, and the bounty of nature. Enjoy the peaceful comfort of the fully equipped small home.

4.94 out of 5 average rating, 145 reviews

A circular fire pit area is surrounded by six blue adirondack chairs, set on a stone patio. Lush greenery and colorful plants frame the space, with a view of the house and pool area in the background. Sunlight brightens the inviting outdoor gathering spot.

Home in Clermont

Spacious Bungalow with Pool and Courtyard

Whether you seek relaxation or adventure, this house offers the best of both worlds! Relax in this spacious bungalow with a courtyard, pool, hot tub, and fire pit! Take a short walk to downtown Clermont and discover the charming shops, restaurants, and breweries! Explore the sights and attractions that Central Florida has to offer! Whether you crave the vibrancy of downtown or the tranquility of your own oasis, this property offers the best of both worlds!

4.92 out of 5 average rating, 135 reviews

Cottage in Clermont

Beautiful country house

Take the whole family to this fantastic place with many areas to have fun. We have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and you will witness a beautiful sunset unparalleled, stay and watch the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and hiking. NOTE: if you want an event, check first for our rates

Popular amenities for Tavares rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 43 reviews

A serene outdoor space is featured, with a sparkling pool reflecting sunlight. Comfortable lounge chairs and a dining table are situated on a wooden deck, providing a perfect area for relaxation and leisure. The pool is enclosed with a screened structure, ensuring a peaceful environment.

Home in Eustis

Heart of Florida❤️ Private pool home

A decorative sign is mounted on the wall, featuring a blue background with white text that reads 'welcome to our happy place.' The sign is framed in a simple wooden border, adding a homey touch to the interior.

4.8 out of 5 average rating, 107 reviews

Carlton Courtyard Villa - Walk to Sumter Landing

4.78 out of 5 average rating, 36 reviews

A spacious bedroom features a modern design with bold black and white patterned accent walls. A large bed is positioned centrally, accompanied by two plush seating areas. Green curtains frame the windows, allowing natural light to illuminate the room, complemented by indoor plants and stylish decor.

Home in Apopka

Casa Esmeralda w/ Kg Bd+Heated Pool+Lanai Bonfire

4.98 out of 5 average rating, 127 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

4.5 out of 5 average rating, 6 reviews

Home in Fruitland Park

Sunny Lakeside Retreat w/ Pool + Firepit

4.79 out of 5 average rating, 43 reviews

A large pool reflects the evening sky, surrounded by a neatly maintained yard. The classic old Florida home can be seen in the background, framed by lush greenery and trees. A fenced area provides privacy and security.

Home in Eustis

Old Florida Charm

4.97 out of 5 average rating, 90 reviews

Home in Clermont

Fun Getaway Ranch Lake Pool Soccer 6 Bed 3 Bath

4.98 out of 5 average rating, 63 reviews

A spacious ranch-style home is set within a large green lawn, featuring light-colored exterior walls and a brown roof. The front porch is accessible from the centrally located entrance, surrounded by a wooden fence and lush trees that provide a sense of seclusion.

Home in Lady Lake

The Promise Land~10 beds~New

Condo rentals with a pool

4.84 out of 5 average rating, 116 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 !

4.89 out of 5 average rating, 188 reviews

A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.

Condo in Kissimmee

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

4.92 out of 5 average rating, 131 reviews

The image captures a vibrant pool area surrounded by lush palm trees and comfortable lounge chairs. An inviting infinity pool is centrally located, accompanied by cabanas and umbrellas. Multiple water slides are visible in one corner, enhancing the family-friendly atmosphere of the space.

Condo in Celebration

Pet friendly Orlando area near ESPN Center

4.97 out of 5 average rating, 429 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.

Condo in Orlando

Waterfront Condo minutes to Disney & Universal

4.92 out of 5 average rating, 165 reviews

A modern living area features a cozy sofa facing a mounted TV, displaying a serene landscape. Behind the sofa, an electric fireplace adds ambiance. The open layout connects to a well-equipped kitchen, enhancing a sense of space within the inviting atmosphere. Accessibility to dining areas is evident.

Condo in Citrus Ridge

Chic Disney Resort Condo • Pool Access Near Parks

4.92 out of 5 average rating, 143 reviews

A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.

Condo in Kissimmee

Modern Condo with Lake View Near Disney 3151

4.91 out of 5 average rating, 174 reviews

Condo in Orlando

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

4.86 out of 5 average rating, 335 reviews

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

Condo in Citrus Ridge

Westgate Vacation Villas - 1 Bedroom

Other holiday rentals with a pool

5 out of 5 average rating, 15 reviews

A Georgian-style mansion features a classic red brick exterior and large windows framed by manicured gardens. The expansive lawn offers lush greenery, while mature trees provide shaded areas. A winding driveway leads to the entrance, enhancing the home's charming presence in a tranquil setting.

Home in Silver Lake

The Silver Lake Estate

4.89 out of 5 average rating, 61 reviews

A lakeside deck features two comfortable chairs adorned with vibrant red fabric, framed by sprawling trees draped in Spanish moss. The tranquil water reflects a colorful sunset, while a small boat is seen in the distance under a serene sky.

Home in Lake Panasoffkee

Pool home on Lake Panasoffkee - Boho Fish Camp

4.86 out of 5 average rating, 44 reviews

The exterior of the home showcases a two-story structure with light grey siding and dark shutters. Lush green grass surrounds the property, and palm trees are visible in the front yard. The garage features a single door, and decorative landscaping frames the entrance.

Villa in Calabay Parc

Calabay Oasis (452 CP)

5 out of 5 average rating, 55 reviews

The modern home features a spacious driveway leading to a large carport and a two-car garage. A covered porch with steps provides access to the front entrance, surrounded by greenery and trees.

Home in Lady Lake

Villages home with unique elevated front porch

4.92 out of 5 average rating, 79 reviews

The kitchen features a blend of modern appliances and rustic charm, with wooden cabinets and a granite countertop. Decorative tiles above the archway add character. Large windows allow natural light to fill the space, enhancing the inviting environment for cooking and gathering.

Home in Mount Dora

Spacious "The Lodge" 3 bed 2 bath Pool home!

4.97 out of 5 average rating, 39 reviews

The outdoor pool area is framed by a screened enclosure, reflecting the warm lights above. The pool water shimmers softly, and a colorful beach ball rests on the surface. A glimpse of the inviting interior, including white furniture, is visible through the large windows.

Villa in Clermont

Luxury home | Lakeside Landing

4.97 out of 5 average rating, 33 reviews

The farmhouse features a classic design with a wraparound porch and decorative elements reminiscent of its historic roots. Surrounded by large trees, its inviting exterior is complemented by American flags and seasonal décor, creating a charming first impression in the serene landscape.

Home in Sorrento

1920 Farmhouse on 6 ac, Chefs kitchen & huge pool!

A decorative entrance sign for Villa De La Vista South is set against lush greenery and vibrant flowering plants. The sign stands prominently atop a circular flower bed, with a clear blue sky and soft clouds in the background.