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Apartment vacation rentals in Winter Haven

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Winter Haven

Guests agree: these apartments are highly rated for location, cleanliness, and more.

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Top guest favorite
A private rooftop terrace features several blue adirondack chairs arranged around a small outdoor rug atop a light-colored floor. Bright sunlight illuminates the space, which is bordered by walls and overlooks a cityscape in the distance. Umbrellas provide shade in select areas.
Apartment in Orlando
5 out of 5 average rating, 108 reviews

Private Rooftop Suite!

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

Top guest favorite
A circular fire pit area is surrounded by multiple light gray Adirondack chairs on a stone patio. The fire pit is filled with glowing flames, creating a cozy atmosphere against a backdrop of a calm lake at dusk, with soft colors in the sky.
Apartment in Winter Haven
5 out of 5 average rating, 22 reviews

Luxury by Legoland 104

Experience comfort and convenience in this stylish 2-bedroom, 2-bathroom apartment, located less than one mile from the LEGOLAND entrance. Situated in a brand-new 2024 luxury complex, this ground-floor unit offers a seamless blend of relaxation & entertainment, perfect for families and theme park enthusiasts. Amenities & Features: • Resort-style heated pool • State-of-the-art fitness center • Fire pits, BBQ grills, and picnic spaces • LEGOLAND-themed kids’ bedroom for a fun, immersive stay

Top guest favorite
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.
Apartment in Winter Haven
4.98 out of 5 average rating, 153 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!

Top guest favorite
A bright workspace is featured, highlighted by large windows allowing natural light to fill the room. A simple desk is paired with a chair, and a vibrant plant adds a touch of greenery. The tranquil view of Lake Morton is visible through the windows.
Apartment in South Lake Morton Historic District
5 out of 5 average rating, 140 reviews

Top 1% Stay – Cozy Lakefront with Hand-Fed Swans

In the Heart of Lakeland, FL... on the Banks of Lake Morton! Nestled between the Historic District and beautiful South Lake Morton Historic District... (or as we like to call it, "Swan Lake") this property is located in easy walking distance to: Restaurants & Shopping Lakeland Public Library The Polk Museum of Art Historic Downtown Lakeland Lake Hollingsworth Florida Southern College Lake Mirror Hollis Gardens AND of course... Lake Morton Take it easy at this unique and tranquil getaway.

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 cozy living area features a comfortable couch adorned with decorative cushions. A coffee table sits in the center, complemented by a small potted plant. Natural light filters through sheer curtains, and a ceiling fan adds a sense of openness.
Apartment in Dixieland
4.88 out of 5 average rating, 354 reviews

2BR/1 Downtown Cozy Hideaway close to colleges.

This cozy mother in law suite is a duplex that shares a wall with the main house but not an entrance. You will be blocks away from a neighborhood playground as well as beautiful Lake Hollingsworth. Being in the heart of Lakeland, you are never far from entertainment or nature. It's almost equally distant from Orlando and Tampa at about a 45-minute drive and the beach being about an hour and 20 minutes away. All that downtown has to offer is just 2 miles away.

Superhost
A modern kitchen area is depicted, featuring a black refrigerator and a microwave mounted above it. Dark wood cabinetry provides ample storage, and a silver kitchen sink is positioned next to a coffee maker. A decorative plant adds a touch of greenery to the countertop.
Apartment in Lakeland
4.83 out of 5 average rating, 126 reviews

❤️ Brand New Modern Studio Perfect for Long Stays

This modern and private modern studio has space for three people, located in one of the best areas of Lakeland, less than 1 mile from Lake Hollingsworth, close to downtown Lakeland and major universities. Close to Disney World and 1 hour from Clear Water Beach. It is a central but quiet neighborhood, close to Publix supermarket, restaurants, gas station and laundry. Without a doubt, a cozy space !!! Don’t hesitate to ask if you have any questions.

Top guest favorite
A comfortable living area features a sectional sofa adorned with cushions in shades of yellow, teal, and deep purple. Two small tables sit in front, accompanied by a patterned area rug, while decorative wall art adds visual interest. Natural light filters through a window with blinds.
Apartment in Bay Lake
4.97 out of 5 average rating, 100 reviews

Charming Oasis 10 Min to Parks Pets Allowed

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Top guest favorite
The spacious bedroom features a queen-sized bed dressed in neutral linens. Light filters through sheer curtains, illuminating a dresser and a television. A bedside lamp adds functionality, while decorative elements enhance the calming decor of the room.
Apartment in Cleveland Heights
4.96 out of 5 average rating, 166 reviews

Hidden Emerald-Apartment with Kitchen and Laundry

Your family will be close to everything when you stay at this centrally-located place. Within walking distance to restaurants, major grocery stores, parks, and much more. Midway between the major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, yard sitting area, washer & dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

Superhost
A modern living space is presented with a futon sofa and a stylish blue accent chair. A round glass coffee table sits on a soft area rug, enhancing the open layout. Natural light filters through the windows, complemented by dark curtains.
Apartment in Kissimmee
4.83 out of 5 average rating, 157 reviews

Spacious Apartment near Disney

Welcome to our cozy and inviting apartment in the heart of The Loop, Kissimmee! Ideally located for both convenience and comfort, this charming space is perfect for couples, solo travelers, business professionals, and those looking for extended stays. Whether you're here for a magical Disney vacation, a work trip, or a romantic escape, our apartment offers the perfect home away from home for all your adventures.

Guest favorite
The exterior of Southeastern University is depicted, featuring a large, arched entrance. The building's beige walls are complemented by palm trees, casting gentle shadows. The university name is prominently displayed above the entrance, contributing to the structured appearance of the campus.
Apartment in Lakeland
5 out of 5 average rating, 22 reviews

Brisa sur

Prime location just 0.7 miles from Florida Southern University in Lakeland. Private accommodation with two queen beds, Smart TV and high-speed WiFi, sleeping up to 4 people. It includes a fully equipped kitchen, plus complimentary coffee and water. Private entrance with smart lock and free parking with 24-hour cameras. Access to common areas with barbecue, trampoline and swing.

Popular amenities for Winter Haven apartment rentals

Quick stats about apartment rentals in Winter Haven

  • Total vacation rentals

    Explore 20 vacation rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven vacation rentals start at € 43 per night before taxes and fees

  • Verified guest reviews

    Over 420 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winter Haven vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Haven rentals

  • 4.9 Average rating

    Winter Haven stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

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