Holiday rentals with a patio in Chesapeake

The Port - Large condo on Mason Avenue!

Welcome to The Portal - a newly remodeled escape in a historic building on Mason Ave. Enjoy modern luxury in the heart of downtown, complete with high ceilings, two spacious bedrooms, two bathrooms, and a gourmet kitchen. Relax on your private balcony with views of the charming Main street below. Property offers 2 coveted off-street parking spaces, 1 golf cart space with charging, and an outdoor shower for beach days. Each room and the living room feature flat-screen TVs for your entertainment.

Historic Charm & Modern Comfort : Downtown Escape

Surrounded by an array of restaurants, bakeries and a variety of unique boutiques and experiences, this apartment offers the perfect blend of charm and convenience. Juliette balconies invite fresh air and natural light, creating a Parisian-inspired ambiance. Inside, a fireplace creates a cozy setting. The state-of-the-art kitchen, designed in a striking 1950s vintage style, features Smeg appliances and bold crimson red accents, seamlessly blending retro elegance with modern functionality.

Cape Cottage B (Upstairs)

Cape Cottage B (upstairs) is an updated & cozy 2BR/2BA duplex perfect for long weekend get-aways to historic Cape Charles. Enjoy coffee or cocktails on the small screened porch or brick patio. We recommend the amazing local restaurants but provide a fully equipped kitchen if you stay in. BR1 has a Queen & BR2 has 1 Bunk & 1 Twin. Each BR has a private BA w/tub shower. In unit w/d for guest use. BYOBeach Towels but use our chairs. Book unit A (downstairs) too if your group needs more room.

Oasis at the Creek| Park, Family & Pet Friendly

Dive into Your Oasis in Deep Creek! Welcome to our 3-bedroom, 2-bath home where the vibes are as laid back as your morning stroll around the neighborhood. Perfect for families, friends, business travelers, or anyone looking to trade city hustle for a serene time. Our home is your ticket to sun-soaked fun and easy commute to local attractions. Located 25-minutes from the local airport, less than 5-minutes from fine dining and local fun. Bring the whole family. Can't wait to host you!

Quiet Suite with Private Entrance

Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

Wave Break Hideaway

Welcome to your perfect beach getaway in Virginia Beach's vibrant Vibe district! Enjoy this centrally located, stylish townhome, located one block from the future Atlantic Park. You're near eclectic restaurants, breweries, and entertainment! Now under new ownership, we're committed to the same attention to detail that made this a top rental in the past. Enjoy sunsets on your private balcony. Ideal for romantic getaways or family vacations. Book now for an unforgettable experience!

The Canvasback Cottage

This unique place has a style all its own. Cottages on the Point was launched in 2018 and offers timeless interior styling and stunning resort style outdoor views. The property features a seasonal (Mid-April to the end of October) 14,000 SF outdoor tiki bar with a shared saltwater pool with swim up bar, outdoor kitchen, and live music. The residences are adjacent to the tiki bar deck and include open layouts, terraces, and custom décor.

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

Captain's Corner

Captain's Corner, The Ultimate Sandbridge Beach Retreat – Luxury 5BR/3BA Getaway! Welcome to Captain’s Corner! Sandbridge’s Premier Beach Escape – a newly renovated, luxury 5-bedroom, 3-bathroom retreat just a 1-minute walk from direct beach access. Whether you're seeking relaxation, adventure, or family fun, this coastal oasis is designed for unforgettable vacations.