Vacation rentals with a pool in DeLand

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Top-rated rentals with a pool in DeLand

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

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Top guest favorite

A sparkling blue pool is centered in a landscaped area, bordered by a smooth concrete deck. Lush greenery and colorful flowers create a serene atmosphere. A shaded seating area is visible in the background, enhancing the inviting outdoor space.

Home in Lady Lake

4.96 out of 5 average rating, 321 reviews

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.

Top guest favorite

The pool area features a large saltwater pool with a paved deck. Several white lounge chairs are arranged near the water, and the back of the property is adorned with windows that provide natural light. Lush greenery surrounds the area, enhancing the tranquil setting.

Guesthouse in Leesburg

4.98 out of 5 average rating, 403 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

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, 332 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.

Top guest favorite

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.

Guesthouse in Deer Island

4.95 out of 5 average rating, 126 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.

Guest favorite

A refreshing pool area is framed by lush tropical plants and features patterned tiles around the edges. Two striped lounge chairs are positioned poolside, facing the water. The charming yellow residence stands in the background, topped with a warm terracotta roof.

Guesthouse in Lake Cherokee

4.97 out of 5 average rating, 109 reviews

1926 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.

Top guest favorite

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

5 out of 5 average rating, 133 reviews

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!

Top guest favorite

A serene outdoor space showcases a solar-heated pool surrounded by lush green palm trees and manicured grass. A comfortable lounge chair is positioned near the pool, while a shaded patio area with a black outdoor seating arrangement is visible in the background, offering additional relaxation options.

Guesthouse in Sanford

4.95 out of 5 average rating, 282 reviews

Palmetto Pool Retreat

The Palmetto Pool Retreat offers complete privacy - detached studio cottage, with a pull-down Queen Murphy bed. * Kitchen - refrigerator, stove, cookware, Keurig , microwave, toaster, dishes and utensils. * Studio Living area - Queen size Murphy Bed, Roku TV, WiFi Internet, AC/Heater; Closet, Iron. Please don’t put AC lower than 72. * Private Bathroom - shower, hairdryer. *Outdoors - Pool, not heated, with private double patio sitting area with 2 Fire pits Gas & Wood; BBQ gas grill

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, 258 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 tranquil pool area is surrounded by a screened enclosure, showcasing a crystal-clear saltwater pool. Comfortable lounge chairs are positioned near the water, and lush greenery, including ferns and tropical plants, enhances the serene setting.

Guest suite in Lake Mary

4.96 out of 5 average rating, 347 reviews

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 tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Top guest favorite

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.

Guest suite in Orange City

4.94 out of 5 average rating, 121 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. :)

Guest favorite

Home in Orange City

4.98 out of 5 average rating, 112 reviews

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

Top guest favorite

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

4.98 out of 5 average rating, 194 reviews

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.