
Apartment vacation rentals in Winter Haven
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Top-rated apartment rentals in Winter Haven
Guests agree: these apartments are highly rated for location, cleanliness, and more.

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.

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

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 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.

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.

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

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.

❤️ 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.

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

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.

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.

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
Weekly apartment rentals

Gorgeous 2bd/2ba oasis w/resort pool near Disney!

*NEW* Villa Amalfi Boho• FreeParksShuttle•PoolView

Modern Condo: 10 Min to Disney + Fireworks Views!

Stunning Resort 2BR Condo w/ Themed Room!

Comfy Reunion Apto /Vista Golf • Piscina y Disney

Comfortable Family Apartment next to Disney World

Lake Hunter Haven- Minutes to Downtown/FSC/SEU

Cozy Apartment Studio by South Lakeland
Private apartment rentals

4 - 1Bed 1bath Retreat in Lakeland

2-Bedroom Loft • Safe and Sanitized Stay

Golf Course View/Free Parking/Pool /Gated/Disney

Bahama Bay Resort-2BR/2BA Near Disney

2BDR Waterview Villa | Pool | 1st Floor

Your Gateway to Adventure and Relaxation

Gorgeous Apt. Near Legoland/Disney & Beaches (#2)

17 minutes to Disney
Apartment rentals with a hot tub

Near Disney Condo 3B2B Pool & Spa at Tuscan Resort

Carmen Romantic Studio W/Private Beautiful Terrace

Cozy Disney apartment

Modern 3 Bedroom Apartment Near the Theme Parks

Shady Lawn Lodge

Gorgeous Award Winning Renovated Mins to Disney

Modern Luxury Kissimmee Retreat

King Bed/Free Shuttle to all Parks/Themed/Pool
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!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- Walt Disney World Resort Golf
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- Streamsong Resort
- Universal CityWalk
- ICON Park