Vacation rentals with a pool in Cypress Gardens

Apartment in Winter Haven

A balcony view overlooks a serene lake, framed by lush palm trees and vibrant green foliage. Bright blue skies and scattered clouds add to the tranquil setting, while glimpses of the driveway and nearby structures can be seen in the distance.

4.99 out of 5 average rating, 150 reviews

Florida Penthouse in luxurious mansion!

Stay in your own themed Florida apartment . Tropical, palm trees, beaches ,marine life, flamingos throughout this stunning apartment in a multimillion dollar home. After parking on gated driveway walk up to your own private entrance way to paradise. Keyless entrance. One flight up and your viewing gorgeous lake views second to none. Executive kitchen with everything you need to cook a 5 course meal. Outdoor balcony that will leave you amazed. Opulence, security, with Florida Style awaits you!

4.96 out of 5 average rating, 162 reviews

An aerial view captures a large pool surrounded by lush greenery and palm trees. Colorful umbrellas and lounge chairs are arranged around a play area featuring a pirate-themed water structure, adding a playful touch to the outdoor space.

Townhouse in Davenport

Luxury Townhouse. Great location nearby Disney.

Beautiful 3 beds, 2-1/2 baths townhome, professionally decorated with all the comforts of home. Perfect place for those who would love to spend time with family and friends to visit the attractions, relax or just to get away. This gorgeous home is the ideal place for your Orlando vacation, look no further, book while it lasts! This property is just 18 mins away from Disney and less than 35 minutes away from Universal , Airport and Downtown. Close to restaurants, supermarkets, pharmacies, etc.

4.9 out of 5 average rating, 117 reviews

The two-story home is illuminated under a night sky, featuring clear glass windows that reflect soft light. Landscaped greenery surrounds the property, with a stone driveway leading to a garage. A large patio area is visible on the right side.

Home in Haines City

Breathtaking Home

New two story home with private pool, patio, barbecue area & game room. Surrounded by parks, gardens, tranquil lakes & walkways with breathtaking views. Resort amenities 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. (Pet free home) 12 mi Legoland/19 mi Disney/26 mi SeaWorld & International Drive/29 mi Universal Studios.

A screened-in pool area is featured, showcasing a well-maintained swimming pool with a soothing spa. Natural light filters in, highlighting the surrounding greenery and the clean stone deck. A peaceful atmosphere is created by the clear blue water and inviting space.

4.88 out of 5 average rating, 113 reviews

Heated pool/hot tub, near Legoland, Disney,

Relax in the heated pool and hot tub after enjoying theme parks such as Busch Gardens, Disney world, and Universal Studios! LegoLand is 1 mile away! Lego bedroom for kids. Centrally Located in the middle of Florida allows beach trips to both east & west coast. air conditioned garage has been turned into a game room pool table, air hockey and a miss pac-man arcade game! Private boat & RV parking with RV outlet thru gate in backyard. Pool can be heated to 85 degrees for a small fee if $10/ day

The exterior of the home features a sleek black façade with large windows allowing natural light in. A neatly landscaped yard includes tropical plants and colorful foliage, enhancing the inviting entrance. The driveway leads to a single-car garage, with ample space to welcome guests.

4.99 out of 5 average rating, 128 reviews

Cheerful 4 Bed, 3 Bath Home with Screened Pool

Just 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.

Guesthouse in Lake Alfred

A screened-in pool area features a clear, inviting swimming pool with a light blue surface. Two striped lounge chairs are positioned beside the pool, and a small seating arrangement is visible in the background, providing a space for relaxation and outdoor enjoyment.

4.94 out of 5 average rating, 177 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 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.

Superhost

Two white domes are situated within a landscaped outdoor area featuring artificial grass and tropical plants. A wooden swing hangs nearby, and a gravel pathway leads through the space, flanked by greenery and decorative lights overhead, creating a welcoming atmosphere.

Dome in Davenport

4.88 out of 5 average rating, 110 reviews

Modern Domes | Pool | Hot Tub- Private Retreat!

Reserve your stay with us now and take advantage of the following amenities: Newly Built- Our facilities are completely new Climate Control- Enjoy cold AC/heat with fans and full insulation for comfort Complete Privacy Pool with pool toys and floats Hot Tub High-Speed WiFi Coffee Bar Hammock for Two Entertainment- TV with Netflix, Hulu, etc. Private Outdoor Shower- Enjoy a hot shower in a secluded setting. Private Fire Pit Variety of Games Secure Location- Gated area with keypad entry

4.94 out of 5 average rating, 114 reviews

Fantastic Water Front Home on the Chain of Lakes

We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitchen with granite counter tops, stainless steel appliances, and numerous appliances. The large TV room features a Samsung smart 65" TV that connects to the Lanai/Pool area. A must see to believe! Numerous pictures provided to allow your mind to wonder. My interaction with you will be based on you. We have keypad entry for your convenience. I am here for you though!

A serene backyard features a clear swimming pool surrounded by a tiled deck. Sun loungers are positioned around the pool, with a shaded dining area beneath a striped umbrella. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.

4.78 out of 5 average rating, 319 reviews

Florida Oasis w/ Pool near LEGOLAND

We have added a modern twist to the design of this 1950's home with all the modern appliances and finishes. This home is nestled in-between 2 lakes among the Winter Haven Chain of Lakes! The backyard is a Florida Oasis of a great pool and pool deck with plenty of fun available with games for you and the kids, or just enjoy laying peacefully in the sun! 2.5 mile drive from Legoland 3.5 mile drive from Downtown Winter Haven with great restaurants and small town unique shops.

A spacious outdoor area features a large swimming pool surrounded by concrete and greenery. Comfortable blue lounge chairs are situated nearby, along with a shaded seating area underneath an umbrella. The brick home, seen in the background, is complemented by large windows allowing natural light.

4.91 out of 5 average rating, 182 reviews

Legoland Lakehouse w/Pool &New AC

Relax in style in this 100 year old custom built home.Tall ceilings,large rooms and wood floors throughout.With an extra large swimming pool overlooking Little Lake Otis this outdoor area is second to none.Less than 2 miles from Legoland,Chain of Lakes Fieldhouse,and Downtown Winter Haven. It is possible that days may be available and not listed on the calendar. This is to give ample time for cleaning. Feel free to ask for additional availability and shorter stays.

A charming lake home is showcased with a light-coloured façade and blue shutters. A welcoming entrance is flanked by decorative chairs, with well-maintained landscaping featuring green grass and flower beds enhancing the outdoor appeal.

4.98 out of 5 average rating, 100 reviews

Lake View, Game Room, 10 min Legoland

Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor games designed w/ family fun in mind! Only 3 min to charming downtown Winter Haven shopping & restaurants, 10 min to Legoland, 30 min to historic downtown Lakeland, & conveniently located between Tampa & Orlando (45 min to Disney & just 60 min to Tampa). We can't wait for you to enjoy the beautiful lakes of Winter Haven at The Elby!