Holiday rentals with a pool in DeLand

Guest house in Port Orange

A private tropical pool area is framed by lush greenery and vibrant plants, complemented by a stone water feature. The sparkling water reflects sunlight, creating a serene atmosphere. Loungers are positioned nearby for relaxation, inviting guests to enjoy the tranquil setting.

4.94 out of 5 average rating, 375 reviews

Relaxing Tropical Pool Get Away Suite

Relaxing Tropical themed pool, spa with grilling area and tiki bar. Private secure parking space near detached suite with gated entry code access. Centrally located to all main area attractions and events. Coffee, shopping, and walking distance from the popular local restaurants and drinking establishments, also two waterfront dog walking parks in the neighborhood. Only 2 miles to beachside. Our home away from home resort is the perfect place to find peace, tranquility and a short stay getaway.

4.91 out of 5 average rating, 332 reviews

A compact kitchen area features modern black cabinetry and a wooden countertop. A stainless steel sink is visible, along with neatly arranged kitchen items. Stairs lead to a private sleeping area, illuminated by warm lighting, and a framed artwork is displayed on the wall.

Boat in Sanford

Unique Concrete House Boat! No cleaning fees!

This ferrocement boat Later Gator was made in Sweden in 1973. That’s right! It’s made of concrete! The boat circumnavigated the globe twice before eventually ending up here in sunny Sanford FL. We spent 2 years completely renovating everything and tried to leave as much of the boat’s original personality intact while adding modern amenities. Restaurant/bar, pool, laundry facilities, showers and restrooms, diner, and marina store all on site, and downtown historic Sanford and river walk close by.

4.98 out of 5 average rating, 412 reviews

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.

Guest house in Leesburg

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

4.88 out of 5 average rating, 589 reviews

A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.

Bungalow in Maitland

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.

5 out of 5 average rating, 133 reviews

A spacious outdoor area is highlighted by a swimming pool and two lounge chairs under a large umbrella. A wooden dock extends over the water in the background, while the expansive water view extends towards the horizon.

Flat in Astor

Sanctuary on Lake George, Waterfront Paradise!

This is a small , attached Mother-in-Law apartment with a separate entrance. Best suited for a family. A waterfront paradise in the Ocala National Forest, down a 4 mile dirt road in a small neighborhood. Located on Beautiful Lake George at the mouth of the St. Johns River, a romantic getaway for two or fun small family water vacation. Close 5 Springs. Popular area for boating, jetskiis, airboats, fishing. Birdwatching, kayaking, canoeing, relaxing or sightseeing, hiking Amazing sunsets!

Guest suite in Orange City

A cozy lounge area features a gray sofa and a small dining table with two wooden chairs. A wall with natural wood accents complements a colorful beach-themed art piece. Light streams through a nearby window, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 127 reviews

The Hillside Haven Oasis

Enjoy a warm and inviting stay in our beautiful Sanctuary in your own private guest quarters, sweetly dubbed, "The Hillside Haven Oasis" This is an extension of our home, similar to a Mother In Law Suite. Only shared space would be the outdoors and we leave that for your private enjoyment. We created this Oasis with a desire is for our guests to feel calm, comfort and tranquility while being showered with Florida Sun. It would be our privilege to serve you as our guests here. :)

4.9 out of 5 average rating, 270 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

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

4.98 out of 5 average rating, 120 reviews

Home in Orange City

The Lemon Cottage -NO EXTRA FEES

Our cottage is nestled in Orange City RV Park. It is your home away from home! Our kitchen is equipped with all pots, pans, and dishes you will need. Our living room has a queen pull out sofa. Our bathroom provides towels, shampoo & conditioner, and a hair dryer. The bedroom has a queen size bed. We are pet friendly; we allow up to two pets. - 20m Daytona Speedway - 26m Daytona Beach - 35m Universal Studios - 41m Disney World - 66m Kennedy Space Center - 73m Legoland

4.96 out of 5 average rating, 107 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.

A spacious studio room is seen, featuring a queen bed with a patterned coverlet and a twin bed that can be converted to a king. Light filters in through large windows, illuminating the room. There is a plush area rug on the floor, adding comfort.

4.87 out of 5 average rating, 167 reviews

Beachfront! Clean City view Studio & beach gear!

Queen and a twin bed that opens to king, stocked with beach gear. We offer beach chairs, umbrella, boogie boards and more for 2. On the beach with city view. Max 4, no pets. No smokers. Light cooking only. No children under 10. WARNING: Resort’s garage and sea wall are not operational Access to beach is adjacent to resort on North side, right next to our beautiful BEACH FRONT POOL! Parking lot is on the South side. We are N Daytona Beach, almost Ormond Beach.

4.89 out of 5 average rating, 105 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 Lake Mary

Markham Woods 4BR Pool Retreat near Attractions

1 camera near the front door for security. Recording 24/7 ANY PARTIES HOSTED WILL BE CANCELED STRICT POLICY 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. Conveniently close to Disney, Daytona Beach, and local attractions for a serene getaway. getaway.

4.98 out of 5 average rating, 194 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

Floating Cottage - Summer/Fall Rates Reduced

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.

Popular amenities for DeLand rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 5 reviews

Home in Lake Mary

Pool House Paradise-Walk to Downtown Lake Mary

4.99 out of 5 average rating, 143 reviews

A charming blue cottage is set within a lush green landscape, surrounded by a white privacy fence. Mature trees provide shade in the background, and a well-maintained pathway leads to the entrance, inviting exploration of the property.

Home in Mount Dora

Mount Dora, FL Private Corner Home w/pool

Home in Colonialtown South

A spacious private pool is enclosed by a screened structure, featuring a basketball hoop at one end. The crystal-clear water is surrounded by a concrete deck, while colorful flags decorate the fencing, adding a friendly vibe to the outdoor space.

4.97 out of 5 average rating, 157 reviews

Private pool home near Downtown

4.98 out of 5 average rating, 144 reviews

Home in Minneola

Pool + Heated spa Family friendly King suite Oasis

4.91 out of 5 average rating, 161 reviews

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.

Home in Orlando

Modern Tropical House Heated Salt Pool

4.88 out of 5 average rating, 162 reviews

The exterior of a two-story Spanish Mission-style home is depicted in soft twilight. The structure features arched entryways with large windows, surrounded by lush landscaping. A decorative lantern illuminates the front entrance, enhancing the inviting charm of the property.

Home in Lake Cherokee

3,000 Sqft Historic Home With Pool Near Everything

4.96 out of 5 average rating, 101 reviews

A bright, inflatable swan floats in a clear, inviting pool. Sunlight reflects off the water's surface, enhancing the serene surroundings. Lush greenery can be seen beyond the pool enclosure, providing a tranquil setting for relaxation.

Home in Canaveral Groves

Serenity in the country with a heated pool!

4.98 out of 5 average rating, 122 reviews

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.

Home in Longwood

Private 4-Bedroom home with pool!

Apartment rentals with a pool

4.9 out of 5 average rating, 110 reviews

A light-filled living area features a soft blue couch paired with a wooden coffee table. Decorative artwork adorns the wall, and a ceiling fan provides ventilation. The open layout offers a view into a dining area with a table and chairs in the background.

Apartment in Sea Woods

Heated Pool * Balcony * Steps To The Beach

Superhost

A wide view of the ocean reveals gentle waves lapping against the soft, sandy beach. The horizon showcases a clear blue sky dotted with a few clouds, creating a serene coastal landscape. The beach area is uncluttered, allowing for tranquil beach activities.

Apartment in Ormond Beach

4.87 out of 5 average rating, 241 reviews

Beachfront Condo with heated pool and epic view

A private balcony offers two white rocking chairs positioned on a patterned rug. The view includes a sandy beach with gentle waves and palm trees lining the shore, under a partly cloudy sky.

4.92 out of 5 average rating, 169 reviews

Daytona Escape

Apartment in Coronado Beach

A modern living area is furnished with a navy blue sectional couch and a geometric coffee table. Large glass doors provide expansive views of the ocean, and natural light fills the space. A wall-mounted television is positioned across from the seating area.

5 out of 5 average rating, 104 reviews

Direct Oceanfront Luxury Suite

4.97 out of 5 average rating, 132 reviews

The image captures a view from a balcony overlooking a heated pool area, surrounded by palm trees. In the background, the ocean is visible, along with beach access and lounge chairs set along the shoreline, inviting relaxation by the water.

Apartment in Sea Woods

Heated Pool | Ocean Views | Direct Beach Access

An aerial view captures the Daytona Beach Resort situated along the coast. The modern building stands beside the beach, with its private access visible. Surrounding areas showcase a parking lot and nearby structures, with the ocean extending into the horizon under a bright sky.

4.81 out of 5 average rating, 186 reviews

Luxury One Bedroom Condo with private balcony

Superhost

A cozy seating area features a dark-toned sofa adorned with a patterned pillow. A mild yellow and teal wall adds character, while three framed prints of beach scenes hang above the sofa. A modern, white coffee table with a potted plant sits centrally.

4.79 out of 5 average rating, 140 reviews

Its a Vibe Beachfront Condo in Daytona Beach

A spacious terrace features comfortable lounge chairs with blue cushions and a stylish hanging chair. A small table accompanies two chairs, providing a perfect spot for relaxation. An umbrella offers shade, while the expansive view overlooks the surrounding area, enhancing the outdoor experience.

4.86 out of 5 average rating, 514 reviews

Lakefront Studio •Private Terrace• near Universal

Home rentals with a private pool

The living area features a spacious arrangement of light-colored leather furniture, including a sectional sofa and additional seating. A dark coffee table sits atop a textured area rug. Soft lighting is provided by table lamps, and the open kitchen can be seen in the background.

10-106 2 Bedroom Condo

A spacious living area features hardwood flooring, complemented by a large gray sectional sofa and a black leather sofa. A glass coffee table sits at the center, with decorative accents noted on the walls. Natural light filters in through sheer curtains, enhancing the welcoming ambiance.

Townhouse in Orlando

Vista Cay Casa Bonita

A spacious dining area features a large wooden table surrounded by upholstered chairs. Natural light fills the room through multiple windows, highlighting modern decor elements. Adjacent to the dining space, a cozy sitting area with a large television and decorative plants can be observed.

Vista Cay Luxury Secret

A furnished lanai with a glass-top table and comfortable seating is visible, featuring tropical-patterned cushions. The space overlooks the pool and landscaped area below, with lush greenery and resort buildings in the background, providing a relaxing view for moments spent outside.

Home in Orlando

Pool View Penthouse - New!

An open-plan living area is showcased, featuring a comfortable seating arrangement with a sofa and armchairs. A light-colored rug is beneath the furniture, and a dining table for six occupies a corner. The modern kitchen is visible in the background, highlighting sleek cabinet finishes.

3 Bed Penthouse Near Convention Center!

A comfortable living area is presented, featuring a modern sectional sofa and a stylish armchair. A dark coffee table is positioned atop a plush blue area rug. Light walls and a piece of wall art enhance the ambience, with a glimpse of the open kitchen and dining area in the background.

7-305 (your Vista Cay)

An open-plan living area features a comfortable sectional sofa, a 46" flatscreen TV, and a light wood floor. A round dining table is set for two, while a modern armchair adds a splash of color. Natural light fills the space through large windows.

Executive Penthouse

An open plan living area is showcased, featuring a spacious seating arrangement with a large sectional sofa. A dining table with ample seating is positioned under a decorative light fixture, while a rug adds warmth to the neutral carpet. Large windows allow natural light to fill the space.