Vacation rentals with a pool in Cypress Gardens

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Top-rated rentals with a pool in Cypress Gardens

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

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Guest favorite

Home in Winter Haven

4.99 out of 5 average rating, 114 reviews

Beautiful Lake House Boating Fishing near Legoland

Welcome to The Executive Lake House ten minutes from Lego Land in beautiful Winterhaven, Florida. The brand new rental home sits on a lake and offers a dock, with boats, fishing gear and beautiful views of the lake. The home offers two bedrooms, a loft , full kitchen and laundry and one full bathroom. The 1100 square foot space which offers 12 foot ceilings and unique interior design will leave you amazed. If your looking for more than a space to sleep but a place to vacation than this is It.

Guest favorite

Guesthouse in Lake Alfred

4.96 out of 5 average rating, 148 reviews

Adorable Agave Suite w/ private pool and entrance

Relax & unwind in The Agave Suite, located in a peaceful lake town. This will be your “shome” away from home. Upon entry of the the property you will find a private back entrance, covered parking, private screened in pool and mature trees. Your guesthouse comes equipped with 1 cozy queen size bed, pull-out sofa bed, walk-in shower, kitchenette, smart tv, wifi and more. Looking to explore? We are centrally located to your nearest parks & Florida attractions. Close to fishing docks & bike trails.

Guest favorite

Home in Auburndale

5 out of 5 average rating, 102 reviews

Private Pool Tropical Garden Oasis, Fenced Yard

Come stay @ "The EstablishMint" while you experience Central Florida! Professionally designed home close to Disney, Legoland, Golf Courses, Lake Myrtle Sports Complex, Winter Haven Chain of Lakes, Waterskiing, Bike Trails. Between Tampa & Orlando. Minutes from Lakeland. Come relax at this clean, modern home. Hang out in the private pool or play yard games. Family & pet-friendly with fenced back yard. Walking distance to Lake Juliana for great fishing and watersports! Extended stays welcome!

Guest favorite

Vacation home in Haines City

4.9 out of 5 average rating, 135 reviews

Updated Southern Dunes Pool Home on Golf Course

We invite you to Stay at our Updated 3 Bedroom Southern Dunes Pool home with a Golf View located in the award winning Southern Dunes Golf & Country Club. Of all Orlando golf courses in the Central Florida area, Southern Dunes may be the most unique. Located between Disney and Legoland, and Central Florida attractions. So whether it's the theme parks, golfing, beaches, shopping, water sports, fishing, relaxing or all of these, you'll find yourself perfectly placed for a great Florida vacation.

Superhost

Home in Davenport

4.89 out of 5 average rating, 122 reviews

Camille's Family Guest Home.

Collecting Memories One City at a Time. Davenport Is The Place To Be. Remember Families That Vacation Together, Stay Together. Come Enjoy This Experience. We are only 20 minutes away from Disney. After a fun-filled day at Disney, you can enjoy our pool and spend time in our game room. We offer FREE WiFi. Must Do's In Davenport Lake Davenport True Blue Winery Providence Gulf Club Time In! (Kids) Fun Spot Crayola Factory All the bedrooms have a 📺 Disney World is about 7 miles away!!!

Guest favorite

Home in Winter Haven

4.99 out of 5 average rating, 109 reviews

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Only 6 miles to Legoland, this stylish home is perfect for vacation. 2 ensuite bedrooms + 2 additional rooms and 2 additional semi private sleeping areas there is room for everyone. Every space is newly furnished with stylish pieces and comfortable beds. The pool area is fully screened so you can enjoy the Florida weather without the bugs. The open concept space is perfect for large groups and families and the kitchen is ready for you to make a meal. A laundry room houses a washer and dryer.

Guest favorite

Home in Haines City

4.92 out of 5 average rating, 100 reviews

Breathtaking Home

New two story home with large private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities are located right across the street with an amazing clubhouse (private owned), Bar & Grill restaurant, water park (extra fee), arcade, gym, volleyball court, soccer & football fields, & event center for parties & weddings. Only 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

Guest favorite

Home in Haines City

4.89 out of 5 average rating, 157 reviews

Southern Dunes Villa - Pool - Golf - near Disney

Stunning executive home with a south facing screened in-ground pool overlooking the 2nd hole of the Southern Dunes Golf Course. Only 13 miles from LEGOLAND and 22 miles from WALT DISNEY WORLD, this is the perfect place to relax after a busy day at the parks. Impeccably maintained, our villa features upgraded furniture, electronics, mattresses and flooring. Southern Dunes is a gated golf community that prides itself on the quality of its golf course and the security and beauty of its homes.

Guest favorite

Guesthouse in Winter Haven

4.87 out of 5 average rating, 254 reviews

The Russell Lake House

This is a Cabana. It has 2 sets of bunk beds (4 total beds). Approx 400 sq. Ft. . Includes a bathroom with sink, toilet, and walk-in shower. AC and heat are available. The property has a pool that can be used while onsite. The entire property's back yard is on a lake (lakefront) with a dock. Ample off street parking, quiet neighborhood with a private entrance for guests. **** we are in the process of rebuilding the dock so it will be unavailable until further notice ****

Guest favorite

Villa in Haines City

4.82 out of 5 average rating, 117 reviews

Sandy's Southern Dunes Villa

This villa is in the Southern Dunes Golf & Country Club, which is an immaculately kept, secure complex, which maintains a 24-hour manned gate, making this a safe place to stay. There are community swimming pools, tennis courts, a gym, library and children's playground for those days when meeting Mickey Mouse is just too much trouble. With a Super-Walmart a minute away plus Dicks and several well-known restaurants just further away, virtually everything is on hand.

Superhost

Guesthouse in Lakeland

4.87 out of 5 average rating, 106 reviews

Luxury Cottage on Prestigious Million$ Property

Close to everything. Away from it all. Situated on 5 grassy acres and home to the Lewman family, this pristine south Lakeland home is fully fenced with a gated entry. The Guest House sits detached next to the main house with plenty of shared parking. Enjoy the outside without the worry of traffic. Free Wifi. We pride ourselves in providing a clean and safe home for you to make your own while you are here.

Guest favorite

Guesthouse in Auburndale

4.98 out of 5 average rating, 217 reviews

Private Poolside Villa

Lovely, private, poolside villa. The apartment is inside a completely enclosed, block walled pool deck. It provides privacy & your own personal oasis! Due to the proximity to the pool, my place is best suited for adults. I will only host young ones 13 & older that are proficient swimmers. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.