Vacation rentals with a pool in Orange City

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Top-rated rentals with a pool in Orange City

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

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Guest favourite
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
4.91 out of 5 average rating, 355 reviews

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.

Top guest favourite
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
4.96 out of 5 average rating, 339 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 favourite
The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.
Barn in St. Cloud
4.97 out of 5 average rating, 178 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

Top guest favourite
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
4.96 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!

Top guest favourite
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, 135 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 to 5 Springs. Popular area for boating, jetskiis, airboats, fishing. Birdwatching, kayaking, canoeing, relaxing or sightseeing, hiking Amazing sunsets!

Top guest favourite
A wooden tray rests across a bathtub filled with warm water, decorated with rose petals. A glass of wine and a small potted plant are placed on the tray, complemented by candles that provide gentle illumination in the background.
Home in Deltona
4.94 out of 5 average rating, 117 reviews

The Great Escape! Explore,Romance, Rest,Relaxation

Welcome to the Inca Inn, a Cozy Private & very spacious home. Romantic & very roomy. Features Beautiful themed bedrooms a Private screened in pool, Tranquil and fenced private backyard. This private house has everything you need for a Business trip, Romantic getaway or a fun family vacation with the kids. The home is central to the beaches & major attractions as well as many parks for biking, running or canoeing. Enjoy nearby restaurants, Golf, Mini golf, Go-Carts, Movie Theater and more!

Top guest favourite
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
4.96 out of 5 average rating, 378 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 jetted tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Guest favourite
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
4.93 out of 5 average rating, 136 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 favourite
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
4.9 out of 5 average rating, 281 reviews

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

Top guest favourite
Home in Orange City
4.99 out of 5 average rating, 147 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 favourite
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, 198 reviews

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.

Top guest favourite
A dedicated pathway leads from a sandy area to the beach, flanked by greenery and palm trees. The ocean is visible in the distance under a clear blue sky, complemented by scattered clouds. The pathway features wooden railings on either side.
Condo in Sea Woods
4.98 out of 5 average rating, 126 reviews

Sea Woods Condo Near Pool and Beach | Bottom floor

Welcome to your next Florida beach getaway! Our cozy first floor (no stairs!) condo is just a few minutes walk, via a dedicated pathway, to the no drive (no vehicle access) part of New Smyrna Beach. It’s across the street from 1 of 3 pools, shuffleboard, tennis, pickleball & clubhouse. It is a short drive to Flagler Ave., restaurants, shopping & more. The Sea Woods community offers 53-acres of old Florida style, including shaded walking and biking trails.

Popular amenities for Orange City rentals with a pool

When is the best time to visit Orange City?

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Quick stats about vacation rentals with a pool in Orange City

  • Total vacation rentals

    Explore 20 vacation rentals in Orange City

  • Nightly prices starting at

    Orange City vacation rentals start at $55 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Orange City vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Orange City rentals

  • 4.9 Average rating

    Orange City stays are highly rated by guests—averaging 4.9 out of 5!