Vacation rentals in Cypress Gardens

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Top-rated vacation rentals in Cypress Gardens

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Guest favorite
Guesthouse in Lakeland
4.96 out of 5 average rating, 190 reviews

Swan City Studio + Cozy Courtyard, near downtown

Your cozy retreat awaits you in Swan City Studio! It is centrally located in Lakeland, a short drive from downtown, Florida Southern College (1.4 miles) Southeastern University (1 mile) The studio comes fully equipped with everything you need to enjoy a relaxing or adventurous stay! Cook a dinner for two in the well appointed modern kitchen! Enjoy a glass of wine in the warm lit courtyard to cap the night! Private parking is just a few steps down the pathway through the courtyard from your door!

Guest favorite
A comfortable bedroom features a spacious queen bed with decorative pillows and a textured blanket. A cozy seating area is positioned at the foot of the bed. A wooden barn door partially covers a window, while a TV is mounted on the wall above a stylish console table adorned with greenery.
Guest suite in Winter Haven
4.9 out of 5 average rating, 200 reviews

2 Bedroom Winter Haven Guest Suite

Private lock-off unit. Only shared between your party. Attached to main home , no shared spaces inside. 1st bedroom -Queen bed and sitting area bathroom attached. 2nd bedroom- two twin sized beds Kitchen and living room included and not shared outside of your party. 3 minutes from Winter Haven hospital. Self check in and out. 20 minutes from Legoland. 45 minutes from Disney and Universal This is an older florida neighborhood with a diverse and working class vibe. Located on Lake Maude

Top guest favorite
A bright sleeping area features a wooden bed frame with a neutral-toned bedspread, accented by a decorative orange pillow. A green chair sits beside a nightstand with lamps. Wall art and a textured hanging piece add character, while natural light filters through the curtains.
Apartment in Winter Haven
5 out of 5 average rating, 30 reviews

Cozy Boho Studio

Welcome to this cozy and stylish retreat! This is a separate private apartment attached to our home. It is cozy and very clean. This thoughtfully designed living space combines modern elegance with comfort, perfect for unwinding after a day of exploring. The space is ideal for relaxing or catching up on your favorite shows. The space has a warm couch/futon and everything you need to feel at home. Ideal for solo travelers or couples looking for a comfortable and stylish getaway.

Top guest favorite
A wooden deck overlooks the calm waters of Lake Ariana, framed by greenery. A small table with two chairs is positioned to enjoy the view, while a potted plant adds a touch of nature to the space. Spanish moss drapes gracefully from nearby branches.
Apartment in Auburndale
4.95 out of 5 average rating, 243 reviews

Ariana Place - Tree House Like Lakefront Views

An Upstairs Sumptuous Tree house (like) Apt on Lake Ariana Waterfront. Upper Outside Deck with chairs & table. Quiet and tranquil with Hi-Speed Wifi for Business Travelers, Smart Antenna TV and Incredible Views for Romantic Get-Aways. Located near Disney, Legoland & Busch Gardens in Central Florida. Luxurious Bedding, Full Kitchen with Coffee & Wine Bar. One Complimentary Bottle of Cabernet per Stay. Sorry, No Pets. No Smoking inside Apt but allowed on property. Save 5% monthly

Guest favorite
A serene pool area is enclosed by a protective screen, featuring a clear swimming pool surrounded by a tiled patio. A comfortable seating area is visible in the background, with a stylish egg chair. Lush greenery enhances the tranquil setting.
Guesthouse in Auburndale
4.98 out of 5 average rating, 241 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. The apartment is behind my personal home with no connecting doors. I live in a centralized location. I am within walking distance to restaurants, park, arcade, gym & library.

Guest favorite
A single-story guesthouse is surrounded by a neatly landscaped yard, featuring a prominent tree in front. The house displays a modern façade with large windows and a black garage door. Soft evening light creates a welcoming atmosphere against a colorful twilight sky.
Guesthouse in Winter Haven
4.92 out of 5 average rating, 91 reviews

Comfy Guest House

Welcome to our inviting and family-friendly guesthouse, designed with your comfort and privacy in mind. Ideal for travellers visiting our wonderful city, our 1-bedroom retreat features a cozy queen bed and a full bathroom, ensuring a relaxing stay for up to 2 guest. The well-equipped kitchen area boasts a sink, refrigarator, microwave, cooking appliances, utensils, and a convenient pantry to store your items. Stay connected with our strong WiFi connection.

Top guest favorite
A comfortable living space features a large sectional couch adorned with decorative pillows. A mirror and wall art enhance the ambiance. Natural light enters through the front door, and a dining table is situated nearby. A ceiling fan provides a refreshing atmosphere.
Guest suite in Winter Haven
4.89 out of 5 average rating, 103 reviews

Cute & Cozy in Winter Haven, Florida

The guesthouse Cute & Cozy is private yet adjacent to the main house (owner lives) and has its own entrance. Located in central Florida, between Orlando and Tampa; 3 miles from Legoland, 5-10 minute walk from shopping and restaurants on Cypress Gardens Blvd. The Cute & Cozy is also in a great location from Florida's amazing beaches, just under 2 hours east or west. Maybe an hour drive to Disney, SeaWorld and Universal (depends traffic)

Top guest favorite
The exterior of the tiny house is showcased, featuring a welcoming front porch with steps leading up. Landscaping includes vibrant tropical plants and a stone pathway. The structure is set against a clear blue sky, highlighting the charming design and inviting ambiance.
Tiny home in Winter Haven
4.9 out of 5 average rating, 135 reviews

4 a Tiny House w/ Bunk Bed in Quiet Marina Unit 14

Our cozy tiny house is perfect for when less is more :-). An intimate space for a long reflective weekend or a more affordable option for a few days with the kids at nearby Legoland. Offering a queen-size Murphy bed and two additional single-size bunk beds, the Cypress Inlet Tiny House can comfortably accommodate up to four people. Equipped with a mini-fridge, a microwave, and a Keurig duo (drip & pod) coffee maker.

Guest favorite
A spacious outdoor area includes a pool surrounded by a white deck. Seating options are available, featuring lounge chairs and tables. The two-story building provides multiple balconies, framed by lush greenery and palm trees, contributing to a serene environment.
Loft in Auburndale
4.93 out of 5 average rating, 223 reviews

2 Bedroom Apartment near Legoland and Disney

This Private Studio features 2 bedrooms, kitchenette with dining area, private bath, walk-in closet, own entrance and from the Main Studio bedroom a large Balcony with Spectacular lake views. The Kitchenette with dining table and the bathroom is located in between of the 2 Bedrooms. The second Bedroom is only 10'x10' with a Queen bed and Wardrobe. Early Check in or late check outs are not available

Guest favorite
A cozy seating area is present, featuring a blue sectional sofa with a decorative pillow and a wooden coffee table. A small TV unit stands nearby, while a piece of wall art depicting a pathway by the water adds visual interest. Soft lighting complements the space.
Guesthouse in Winter Haven
4.83 out of 5 average rating, 6 reviews

Winter Haven Guest Suite

Winter Haven Guest Suite, your perfect getaway in the heart of FL! Nestled in a quiet neighborhood, our private 550 sq ft Studio guest room offers comfort & convenience. It is centrally located, less than a mile from Lake Summit Boat Ramp, 1.4 miles from Legoland, 2 miles from AdventHealth Fieldhouse, 4 miles from the Country Club of Winter Haven and 5 miles from Cypresswood.

Guest favorite
A spacious living area is presented with a sectional sofa, a wooden coffee table, and a wall-mounted television. Large windows allow natural light and views of the outdoor patio. The room features light-colored walls and art pieces that add a modern touch.
Home in Winter Haven
4.95 out of 5 average rating, 133 reviews

Legoland Getaway 7 mins • Sleeps 7 • Elevator

Come relax with your family in this peaceful 2BR/2.5BA home, just 7 minutes from LEGOLAND®. Sleeps up to 7 guests, with pool access, board games, and arcade fun for all ages! Wheelchair accessible with elevator between floors. No parties, no smoking. Primary guest must be 25+ and present during stay; ID may be required.

Superhost
A living area features a blue sofa adorned with decorative pillows, a wooden coffee table, and a cozy armchair. A wall-mounted television is positioned above a white fireplace. Natural light filters through a window with sheer curtains, while a wooden table stands against the wall.
Apartment in Dixieland
4.89 out of 5 average rating, 205 reviews

Adorable 1 bed/1bath with office and free parking

This beautiful duplex is located in a Historic Bungalow built in the late 1920s, centrally located in Lakeland downtown. Nice park across the street for exercising or spending time with kids. Walgreens is one block away, and local bars, restaurants, antique stores, and lots of beautiful historic bungalows

Popular amenities for Cypress Gardens vacation rentals

When is the best time to visit Cypress Gardens?

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Avg. priceG$23,430 GYDG$26,358 GYDG$26,149 GYDG$26,149 GYDG$26,149 GYDG$25,731 GYDG$26,777 GYDG$23,639 GYDG$22,384 GYDG$25,940 GYDG$26,149 GYDG$26,149 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • Do house rentals in Cypress Gardens have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Cypress Gardens have free parking?

    Absolutely! We offer over 10 hotel rentals with free parking in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Cypress Gardens?

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with air conditioning, over 60 homes with a kitchen, over 60 homes with wifi, over 60 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Cypress Gardens have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • Are there Cypress Gardens vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Cypress Gardens, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly vacation rentals in Cypress Gardens?

    Cypress Gardens has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Cypress Gardens?

    Four-legged friends are welcome in Cypress Gardens. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Cypress Gardens?

    Yes! Work meets play with ease at over 60 vacation rentals in Cypress Gardens featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Cypress Gardens have wifi?

    Absolutely! We offer over 20 hotel rentals with wifi in Cypress Gardens. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Cypress Gardens?

    Experience the best of Cypress Gardens with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Cypress Gardens

  • Total vacation rentals

    Explore 110 vacation rentals in Cypress Gardens

  • Nightly prices starting at

    Cypress Gardens vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,480 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Cypress Gardens vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cypress Gardens rentals

  • 4.7 Average rating

    Cypress Gardens stays receive an average rating of 4.7 out of 5 from guests

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