Holiday rentals with a pool in Portsmouth

Cavalier Manor: Pool, Luxury Home, & Scenic Views

Escape to the Cavalier Manor, a luxurious 6,000 sq. ft. estate where elegance and relaxation converge. Start your day with freshly ground coffee from our Bosch coffee maker. Enjoy the sun by the pool and indulge in gourmet meals in the outdoor kitchen. Our spacious bedrooms with plush mattresses promise serene rest. Savor stunning lake views and embrace tranquility. Ideal for a peaceful retreat or a memorable family vacation, this estate offers a unique blend of comfort and sophisticated living!

Unique 1 Bedroom Apartment in Bridgeport

A unique location featuring one bedroom, one bath and a sleek living area design. Find this loft in the Bridgeport community, above the state-of-the-art Blue Hippo Car Wash. Fear not, the only audible sound in your loft is an ambient white-noise-like humming. This space gives you an exceptional birds-eye view of the surrounding area along with a secluded bal- cony where you can kick back and relax. Enjoy access to the season pool, fitness center, and clubhouse at 3800 Acqua. No elevator access.

Elegance Escape on Saunders Dr

Experience all that Portsmouth has to offer from this 3-bed, 2-bath vacation rental! This home features 5 Smart TVs, a fully equipped kitchen, and an awesome outdoor space fit for the whole group. Get outside and enjoy a morning stroll through Portsmouth City Park, then hit the links at Elizabeth Manor Golf and Country Club! For the art fanatics, visit the Chrysler Museum of Art. Following your leisure, cool down with a dip in the pool or gather around the fire pit for stargazing and s’mores.

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

"Shangri-La", of Hampton, Virginia

2nd story 1200 square foot apartment with 2 BR's, Wi-Fi, microwave, fridge and bar with sink. Walk in glass enclosed shower & soaker tub. Private deck with gas grill down the spiral stairs below on ground level patio. Pool table in BnB. We share our pool with our BnB guests seasonally. Please inquire about pool availability if important to your booking. Local history, sites, nature and beaches abound. Security cameras surround the exterior of our home for our protection as well as yours!

Gorgeous Vacation House

This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

Half house w/pool & new patio all to yourself

PLEASE READ TO THE END!!!!!! Our home is close to restaurants, parks, the resort oceanfront and art and culture. You’ll love our place because of the location and the ambiance. Our space is good for couples, solo adventurers, business travelers or small families. Please know that my wife and I live in the other half of the house. There is NO shared space!!! You have a private entrance with full & private access to all amenities. Our home is LGBTQ+ friendly because LOVE IS LOVE!

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

Welcome to the Blue Octopus! This charming coastal retreat offers comfort and convenience for your seaside escape. Just a short walk to the beach, it's perfect for families, couples, or solo travelers. Location Highlights: 3 minutes to the beach 10 minutes to restaurants & Norfolk Naval Base 15 minutes to outlets 20 minutes to VA Beach Features: Private Pool Hot Tub Outdoor Movie Projector BBQ Grill Home Office Smart TV & Wi-Fi Kid-Friendly Book your stay today!

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

4BD home w/ game room & pool near Langley & PTC!

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!