Holiday houses in Highland City

4.85 out of 5 average rating, 185 reviews

A small outdoor seating area is presented with a black round table and two folding chairs, situated on a green lawn area. A door adorned with a floral wreath provides access to the suite. Surrounding plants add greenery to the tranquil space.

Guest suite in Lakeland

Private Studio Suite

🧳 Perfect for a solo traveler or couple looking to visit the peaceful city of Lakeland. 📍Located about 40 minutes from Tampa and an hour from Orlando, in the family friendly area of Lakeland Highlands. - There’s nearby trails, grocery stores, convenience stores and eateries. - Polk Parkway is less then 10 minutes away, it’s the quickest route to get to i4. 🏠 The suite includes a private entrance with full bathroom and backyard area. 🚗 Free Parking Space(s) 👐🏽 Flexible & Contactless Entry

4.96 out of 5 average rating, 305 reviews

Guesthouse in Lakeland

Cottage On Cambridge-Lake Hollingsworth/FSC Area

This cozy Studio Cottage is located steps away from Lake Hollingsworth and close to Florida Southern College. It's a separate home located behind the main one and is private. You can enjoy all outside living areas. If you've stayed in previous years it’s unrecognizable from before! I'm just re-listing after almost 2 years when Hurricane Milton decided to crash it with our big Oak tree. The Cottage has been completely rebuilt! Landscape is so different without our beloved Magnolia and Oak trees!

The exterior of a spacious house is displayed, surrounded by lush green grass and mature trees. A pathway leads to the entrance, flanked by shrubbery. Bright daylight emphasizes the clean lines of the house and the inviting front porch.

4.98 out of 5 average rating, 47 reviews

Tranquility! Cozy and quiet home

Spacious house on a quiet street where you can relax and recharge during your central Florida vacation. Sleeps up to 7 people. Guests have access to a full kitchen, a dining room, a large living room and a patio. Guests can also park up to two cars in the enclosed garage and do laundry in the laundry room. Master bedroom has a king size bed, an en-suite bathroom and a walk-in closet for anything you need to store. bedroom two has a king size bed. bedroom three has one queen and one double bed.

5.0 out of 5 average rating, 51 reviews

Family Heated Pool Home Sleep 12 Near Tampa Disney

Wake up to sunshine, step outside to your PRIVATE HEATED POOL, and let the day unfold at your own pace. This is where FAMILY MEMORIES ARE MADE: kids laughing in the playground, slow mornings with coffee poolside, and evenings enjoying movie nights on the 75” TV. Tucked in one of Lakeland’s most peaceful neighborhoods, this spacious retreat is designed for connection and comfort. About 1 hour from Tampa or Disney, Publix minutes away, quick access to SEU, Florida Southern College, and Polk State.

An open living space features a dining area with a floral tablecloth and wooden chairs. Adjacent, a cozy seating area includes a light fixture and a large window providing natural light. The polished tile flooring reflects the warmth of the interior.

5.0 out of 5 average rating, 65 reviews

Edinger's Nest

Relax with the whole family in this natural setting with abundant birds and wildlife. Host has garden next door with seasonal fruits and vegetables. Located in central Florida between Tampa and Orlando. Easy access to I-4 with a short drive to Disney, Busch Gardens, and Legoland. Directly across the lake from the Detroit Tiger's Stadium with beautiful sunset views and home game Sat. night fireworks. 5 min. drive to Southeastern U. 10 min to Florida Southern U. & 14 min to Florida Polytechnic U.

The living room features a vintage vinyl record wall that adds character. A spacious white sofa and a brown leather couch are positioned for relaxation. Natural light filters through shuttered windows, illuminating the hardwood floor and a round area rug with a geometric pattern.

4.96 out of 5 average rating, 102 reviews

LKLD Legacy near Downtown Lakeland

The LKLD Legacy is a midcentury ranch, and third generation owned home, in the heart of Lakeland. It's located 5 minutes from downtown, near colleges, and close to I4 exits toward Tampa & Orlando (37mi to Disney, 19mi to Legoland)! The home is in a family-friendly neighborhood and within walking distance to parks and lakes. The large fenced in backyard is perfect for kids and pets (*pet fee required*). Before you leave, snap a photo with the instant camera and add it to our guest photo album!

The open living area features a comfortable sofa set, a stylish area rug, and large windows allowing natural light to fill the space. An island kitchen with contemporary bar seating and modern appliances is visible, creating a seamless flow between dining and living spaces.

4.98 out of 5 average rating, 184 reviews

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!

Home in Lakeland Highlands

The Highland House • Cozy 3BR • Fireplace • Patio

Stylish and spacious, this South Lakeland retreat is the perfect home base for your stay. Enjoy a beautifully updated interior with an open-concept layout, modern kitchen, and cozy living space for relaxing or gathering. With comfortable bedrooms, a large dining area, and plenty of room to unwind, it’s ideal for families, groups, or work trips. Features a screened patio, fenced yard, and keyless entry, all in a quiet neighborhood close to shopping, dining, and local attractions.

5.0 out of 5 average rating, 18 reviews

4.97 out of 5 average rating, 38 reviews

“Pool Retreat, Sleeps 10. Near Downtown Lakeland”

Welcome to this beautiful house with a pool in Lakeland, ideal for families and groups of up to 10 guests. Large pool with a covered terrace, lounge chairs and a grill. 3 bedrooms, 6 comfortable beds and 3 full bathrooms. Equipped kitchen, washer and dryer. Fenced garden, perfect for children. Close to downtown, Lake Hollingsworth, and parks. Legoland is 25 minutes away, Tampa is 45 minutes away, and Orlando is 1 hour away. Self check-in, fast Wi-Fi, and EV charger.

The saltwater heated pool is enclosed within a screen patio, surrounded by a well-maintained white fence. Comfortable cushioned seating is visible nearby, along with potted plants adding a touch of greenery. Clear blue skies enhance the peaceful atmosphere of the outdoor space.

4.85 out of 5 average rating, 40 reviews

Relax in Heated Saltwater Pool w/ Screened Lanai

Experience luxury and comfort in this spacious rental featuring a master suite with king bed and en suite bath, fully equipped kitchen, dedicated office, and cozy living areas. Enjoy a heated saltwater pool, outdoor TV, grill, and large fenced yard. All bedrooms have large beds, TVs, and ample storage. Includes free WiFi, private driveway, and welcome snacks. Perfect for families, couples, or business travelers!

4.99 out of 5 average rating, 125 reviews

A modern living area features a sectional sofa adorned with blue and white decorative pillows. A round coffee table with a marble top sits on a textured area rug. Natural light fills the space through sheer curtains, complemented by a stylish console table and a round mirror.

Home in Winter Haven

Cozy 3 bedrooms 2 bathrooms

Relax with the whole family at this peaceful and charming home in Winter Haven.This home is centrally located and is within walking distance to Lake Howard , downtown winter haven and plenty attractions We are located 10 minutes from Legoland, Peppa Pig Park, five minutes to Advent Health Fieldhouse, five minutes to Winterhaven Hospital, 45 minutes to Walt Disney World, SeaWorld and Busch Gardens.