Family-friendly holiday rentals in Pearl

The Funky Monkey Cottage in Fondren!

The Funky Monkey is a 1bedroom cozy, whimsical, historic cottage brimming with charm in the heart of Fondren! The perfect spot for a quiet romantic weekend, a last-minute getaway, or a family trip to the famous Hal's St. Paddy’s day parade. Within walking distance to local restaurants, coffee shops, boutiques, movie theatre and music venues and a short drive to all major medical facilities, universities and museums. The Funky Monkey Cottage is the most unique spot for your Jackson adventure!

*Home away from home! Studio suite/peaceful farm

We have renovated from floor to ceiling! Our fresh, clean space is exactly what you need for any occasion - whether you need a break from the daily grind or you’re just passing through. We provide a warm, comfortable environment and top-tier hospitality to make you feel like a friend, not just a visitor. We’re located at the end of a quiet, friendly street just minutes from downtown Raymond. During your stay, you'll have access to our gorgeous land including a play set, farm animals, and more!

Stay Local - Game Room near Ampitheater / Baseball

Come and experience luxury and fun at our fully equipped airbnb! Our spacious 3BR 2BA property can comfortably accommodate up to 8 guests with its king, queen, full & twin trundle, twin fold out, memory foam mattresses. Immerse yourself in endless entertainment in our game room with a 4500 game arcade, foosball, air hockey, shuffleboard and more. The fully equipped kitchen and outdoor gas grill allow for convenient cooking and dining. Book now and make lasting memories with friends and family!

SunChaser 042

Welcome to SunChaser 042 •Game Room: Enjoy hours of fun with a well-equipped game room. •Professional Landscape Backyard: Relax in our beautifully landscaped backyard. Gather around the fire pit for a evenings under the stars. •Stylish Interior: Our home is designed by a professional interior decorator. •Attractions: Conveniently close to Brandon’s entertainment and shopping options. We look forward to hosting you and ensuring you have a fantastic stay in Brandon, Mississippi!

The Modern Hideaway

Welcome to your unique private oasis, where modern minimalist decor meets serene tranquility. This thoughtfully designed space features open-concept living areas filled with natural light and stylish furnishings, ensuring a comfortable and chic retreat. Step outside to discover your own private backyard space, perfect for relaxing or entertaining. Experience a getaway that makes an ideal choice for those seeking both comfort and privacy. Unwind and recharge in a world of modern comfort!

Relax in Architecture! Secluded, Safe, and Serene.

Welcome to the Falk House! Listed on the National Register of Historic Places by the US Department of the Interior, the Falk House is a treasure of mid-century modern design. We've transformed the original art studio into a stylish, private oasis, with expansive views of nature and Eastover’s Upper Twin Lake. You will be central to all metro destinations, including amazing restaurants, bars, and shopping, as well as area hospitals, courts, and businesses. Long stays ideal.

Modern Farmhouse w/ Gameroom + Close to Everything

Newly remodeled farmhouse in the perfect location. Fully stocked kitchen, on site laundry, outdoor gathering with fire pit. The game room has pool table, arcade games, karaoke machine, and extra large projector. Perfect location within 15 minutes of Downtown Jackson, outlet mall, Mississippi Braves, Brandon Amphitheater, golf courses, JAN airport, Tesla, several museums, & more. If you need a car, we can accommodate you through Turo. Just message us for availability.

Hospitable Reservoir home w/King Bed near Shaggy’s

If you want the best food, a comfortable stay, and a place that feels like home, look no further than staying on the Rez Cottage. Walking Trails, Water Activities, and Parks are nearby. This fully furnished Cottage will have the perks of Simple Luxury without the hassle of the upkeep. Come stay for a Week or an Extended Weekend to enjoy all the Reservoir has to Offer. This property has a Beautiful Master Suite with a King Bed and Two Adjacent Bedrooms with a Queen Beds

Downtown Apartment, Close to the Best of Jackson

Long-term discounts now available. Welcome to this cozy one-bedroom apartment in a quiet, safe neighborhood minutes from the heart of downtown, Belhaven university, and Millsaps. This well-lit space is part of a 1940s duplex with off-street parking and a private yard for outdoor relaxation after a long day-- perfect for business professionals and cultural enthusiasts. By default we do not allow pets, however we are open to it with conditions so please request first.

The Cottage on College Near Downtown Brandon

Welcome to The Cottage on College, a cozy, private and pet-friendly guesthouse in Brandon’s Historic District. Enjoy vintage-industrial charm, a peaceful setting and easy access to Downtown Brandon, less than half a mile away. We’re approximately six minutes from the Brandon Amphitheater, near Shiloh and Quarry parks, and about 13 minutes from JAN Airport—ideal for concerts, tournaments, work trips, weekend getaways and longer stays.

Belhaven Guest Suite - Private

Cozy private guest suite in Belhaven home with vintage kitchenette, queen bed, full pullout sofa, Keurig, toaster oven, microwave, hotplate, oven, and fridge. Private entrance and space to a single-family home in a beautiful neighborhood. Nearby Belhaven University, Millsaps College, hospitals, and downtown. Ideal for solo travelers, couples, small families, or those traveling for work.

Hope's Treasure

Hope's Treasure is just that--a sweet retreat less than 15 minutes from Mississippi College and Hinds Community College. With 2 bedrooms, a private bathroom, a comfortable living room, and a kitchenette, you can relax and enjoy some beautiful sunsets in a peaceful wooded setting. A picturesque half-mile drive leads from the gated entrance to your getaway.