Vacation rentals with a pool in DeLand

Guesthouse 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, 373 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.

4.96 out of 5 average rating, 325 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.

4.98 out of 5 average rating, 411 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.

Guesthouse 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, 588 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.

Guesthouse in Deer Island

An outdoor patio area features a screened enclosure with a private swimming pool. Comfortable seating is arranged around the pool, and lush greenery surrounds the space, providing a serene environment. Potted plants add a touch of color, enhancing the tranquil setting.

4.95 out of 5 average rating, 127 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.

Guesthouse in Lake Cherokee

A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.

4.97 out of 5 average rating, 113 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

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.

Apartment 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!

4.87 out of 5 average rating, 260 reviews

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

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!

4.91 out of 5 average rating, 331 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 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.

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, 124 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

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, 12 reviews

A spacious living room features comfortable seating arranged around a central coffee table. Large sliding doors open to an outdoor area, while bright, natural light illuminates the room. Modern appliances and a dining area are visible in the background, enhancing the inviting atmosphere.

Home in Deltona

Relaxing Stay with Private Pool/ Near Orlando

5 out of 5 average rating, 24 reviews

A heated pool is framed by a screened enclosure, surrounded by a spacious patio. Two lounge chairs provide a relaxing space, while a basketball hoop is seen at one end of the pool. The sky above is a blend of evening hues, enhancing the tranquil atmosphere.

Home in Deltona

Chamorro Retreat Home with Heated Pool

4.99 out of 5 average rating, 142 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

4.99 out of 5 average rating, 151 reviews

A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.

Home in Sanford

The Cypress House

4.87 out of 5 average rating, 133 reviews

A spacious living area features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.

Home in Maitland

Bonheur Ala Maison

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, 154 reviews

Private pool home near Downtown

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, 160 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

Condo rentals with a pool

4.96 out of 5 average rating, 107 reviews

A private balcony offers views of the shared pool area surrounded by palm trees. Sunlight brightens the space, highlighting a comfortable chair and the well-maintained grounds below. The inviting atmosphere allows for relaxation while enjoying the warm ocean breeze.

Condo in Sea Woods

Beachfront | Ocean View | Heated Pool

A spacious studio features two large beds with light-colored bedding, positioned near expansive floor-to-ceiling windows that provide unobstructed ocean views. A contemporary television is mounted on the wall, and a palm plant adds a touch of greenery to the room.

4.98 out of 5 average rating, 132 reviews

Breathtaking Direct Oceanfront

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

4.86 out of 5 average rating, 100 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

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

5 out of 5 average rating, 104 reviews

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.

Condo in Coronado Beach

Direct Oceanfront Luxury Suite

4.98 out of 5 average rating, 129 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.

Condo in Sea Woods

Heated Pool | Ocean Views | Direct Beach Access

Two queen size beds are positioned against a green accent wall, featuring floral-patterned bedding. A large window allows natural light to fill the room, revealing beach views. A lamp is placed on a nightstand, enhancing the cozy atmosphere of the sleeping area.

4.87 out of 5 average rating, 276 reviews

Relax & Recharge | Wake Up to the Waves |Oceanview

Superhost

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, 185 reviews

Luxury One Bedroom Condo with private balcony

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 is furnished with a light grey sectional sofa and a circular glass coffee table. Soft pillows add comfort to the seating. Two table lamps provide gentle illumination, while large windows allow natural light to fill the room. A textured area rug complements the decor.

Vista Cay Lakeview Elysium

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.