Accommodation with a pool in Longwood

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Top-rated rentals with a pool in Longwood

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

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Guest favourite

Guesthouse in Leesburg

4.98 out of 5 average rating, 333 reviews

Silver Lake Guest Pool House

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.

16 – 23 Oct

$1,199 AUD total

Guest favourite

Bungalow in Maitland

4.86 out of 5 average rating, 493 reviews

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.

11 – 18 Aug

$1,197 AUD total

Guest favourite

Home in Deltona

4.96 out of 5 average rating, 150 reviews

St. John’s Luxury Pool Lake House

Centrally located 30 min. to Orlando and Daytona beach, 15 min to Boombah. Beautiful 5/2.5 resort like home on a canal that leads directly to Lake Monroe & St. John’s River. 3000 sq ft of living space plus 3500 sq ft of outdoor space that is completely screened in! Enjoy Florida lifestyle in the massive outdoor space that has a sparkling pool, seating, dining, & lounging areas including a gas grill. Close to shopping, Boombah,and 5 parks nearby. Once you’re here you will never want to leave!

30 July – 6 Aug

$5,641 AUD total

Guest favourite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 317 reviews

St Augustine suite

Luxurious space with PRIVATE ENTRANCE, PRIVATE 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 , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

12 – 19 Aug

$1,146 AUD total

Guest favourite

Guesthouse in Sanford

4.95 out of 5 average rating, 227 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 - Solar heated pool(not propane heated) with private sitting area with 2 Fire pits Gas & Wood; BBQ Gas

25 Feb – 4 Mar

$1,466 AUD total

Guest favourite

Guest suite in Oviedo

4.9 out of 5 average rating, 315 reviews

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and guests have complete privacy. There are no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge , microwave, TV, Wifi and access to non-heated swimming pool. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles

20 – 27 Feb

$1,323 AUD total

Guest favourite

Home in Maitland

4.94 out of 5 average rating, 148 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

19 – 26 Mar

$2,728 AUD total

Guest favourite

Guest suite in Lake Mary

4.96 out of 5 average rating, 287 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

29 July – 5 Aug

$1,718 AUD total

Guest favourite

Guesthouse in Mount Dora

4.9 out of 5 average rating, 707 reviews

Key West cottage of Mt Dora

Cozy little cottage located in the gardens of the main house. It has a full kitchen. 1 bath with a jacuzzi tub.. Queen size bed and a couch for a 3rd person. THE LOCATION is 3 MILES between Mount Dora ,Tavares & Eustis a short drive or bike ride to all location. I’m 2.5 blocks off Lake Shore Dr. to beautiful Lake Dora. FRESH eggs from the Easter egg hens for your use ( When available) The eggs they lay are pink, green and blue. They will need to be washed before use..

27 Oct – 3 Nov

$1,638 AUD total

Guest favourite

Home in Sanford

4.86 out of 5 average rating, 214 reviews

Private Pool at Flamingo Cottage

This 3 bedroom, 1.5 bath is equipped for a peaceful stay! A mile off 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 – 11 Sept

$1,974 AUD total

Guest favourite

Guest suite in Orlando

4.92 out of 5 average rating, 317 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

16 – 23 Aug

$1,896 AUD total

Guest favourite

Houseboat in Sanford

4.98 out of 5 average rating, 177 reviews

Floating Cottage - Sweet River Retreat in Florida

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.

15 – 22 Oct

$2,122 AUD total