
Holiday rentals in Lakeland-Winter Haven Metropolitan Area
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Lakeland-Winter Haven Metropolitan Area
Guests agree: these stays are highly rated for location, cleanliness and more.

Sunshine Studio + Courtyard, Firepit, near downtwn
Your cozy retreat awaits you in Sunshine 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!

The Studio - LKLD
The Studio, stylish and comfy, is located on our home property. With easy access to I-4, you are a short distance from Tampa, Orlando, and many of our beautiful beaches! You are also a 15 minute drive to Southeastern University, Florida Southern College, downtown, and many of our amazing and unique local businesses! With a central location like this, there’s nowhere you can’t go. Nestled in a quiet neighborhood, it’s the perfect weekend stay! Disclaimer: There are chickens & roosters around.

Serenity at Success
Nestled in the heart of the Lake Morton Historic District, this completely detached private suite offers both charm and convenience. Just a 2-min walk to Lake Morton, home to Lakeland’s famous swans, and only half a mile from Lake Hollingsworth, a favorite spot for walking, running, and cycling. FSC is just one block away, making this an ideal stay for campus visitors. Enjoy a leisurely one-mile stroll to downtown Lakeland, where you’ll find an array of restaurants, bars, and boutique shops.

Charming Tiny House on 5 acres with POOL/ HOT TUB
Escape to the heart of Lakeland where our charming Tiny House awaits. Nestled on 5 acres of tranquility, you'll experience the best of both worlds: a peaceful retreat and easy access to local shopping centers just a stone's throw away. The Tiny House is furnished with a queen size bed and a king sized bed in the upstairs loft, kitchen, full bath as well as a designated work area. Take a refreshing dip in the shared pool, unwind in the hot tub, or simply soak up some sun on the lounge chairs.

La Casita Azul
The Little Blue House is a studio,guest house in our backyard. The backyard, which includes a covered deck, comfortable furniture, and a TV, is yours to enjoy. Separate entrance on the opposite side of the main house. This cozy comfortable room has a microwave, small refrigerator/freezer, and Kurig coffee maker( coffee included).It is perfectly located in the historic East Lake Morton, walking distance to Lake Morton, Lake Mirror, and downtown Lakeland. Perfect location to enjoy Lakeland.

Romantic Lakefront – Feed Swans – Walkable Dining
Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

Gorgeous Gem in the Heart of Lakeland
LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Charming Historic Area Retreat!
Welcome to our charming one-bedroom short-term rental nestled in the scenic Lake Morton Historic District and conveniently located near the prestigious Florida Southern College. This thoughtfully designed accommodation offers a perfect blend of modern comfort and historic charm. Situated just a stone's throw away from the beautiful Lake Hollingsworth and Lake Morton our property provides an easy access to leisurely strolls around the lake and jogging trails.

Central Location, Charming Historic Bungalow
Craftsman style bungalow on quiet, cobblestone streets in a beautiful Historic District. Enjoy the neighborhood park, sip a latte at the Hillcrest Coffee Shop, enjoy the birds and wildlife of Lake Hunter or take a short walk to downtown Lakeland with it's many wonderful restaurants, entertainment venues and more beautiful lakes. The RP Funding Center is a 10 minute walk away and the location also provides easy access to I-4 for trips to Tampa or Orlando.

Quiet, Clean, and Cozy Apartment
This is a 300 square foot comfortable spacious efficiency apartment. You have complete privacy like a hotel suite. There is parking right by the apartment and a private wooden gate and entrance. There is a small kitchenette with a microwave, a comfortable bed, new bathroom, dining table for two, and more! The entire space is yours to enjoy. This is a very quiet and safe location. It is close to stores, restaurants, and a shopping mall.

Historic District Home w/ King Bed Near Downtown
📍Lakeland Historic District — Just a 10 minute walk to Florida Southern College (FSC) & 4 minutes walk to Morton Lake (aka ‘Swan Lake’) Highlights: → Located in the 1920s character filled historic district → Walking distance to prime downtown Lakeland, FSC & Morton Lake → Fully stocked kitchen with cooking essentials → 70” Samsung SmartTV for entertainment → Backyard with BBQ grill and outdoor dining → Dog friendly accommodation

Modern lakeside retreat by SEU and FSC
This 1920’s 1 bedroom 1 bath lakefront historic cottage is separate from the main house with its own entrance, parking, front porch & beach. The queen bed and large couch sleeps 3 adults. Only 1 mile from Southeastern University and 3 miles to Florida Southern College. Kayaks, pedal boat, and fishing poles and tackle are provided for your enjoyment. Come unwind and enjoy the lake views from the hammock and private beach!
Popular amenities for Lakeland-Winter Haven Metropolitan Area holiday rentals
Other great holiday rentals in Lakeland-Winter Haven Metropolitan Area

Stylish Bungalow 3 Bedroom Near Downtown Lakeland

Family & Pet-Friendly Stay Near Tigertown

Luxury 3BR Near Downtown | Pet Friendly + Peaceful

Cozy Private Studio

Private Bungalow In Peaceful Downtown Lakeland

The Studio Collection

Luxury Cozy Home·3BR/2BA· Dixieland Lakeland

The Lakeland Cottage.
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Give Kids the World Village
- Orlando / Kissimmee KOA
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Universal's Volcano Bay
- Vinoy Park
- Amalie Arena
- Aquatica
- Island H2O Live!




