Vacation rentals with a pool in St. Mary's County

Waterfront Paradise with a Private Pool

Set on three acres of spectacular waterfront property, there’s everything you need to escape – a dock, a fire pit, crab traps, kayaks, bikes and a POOL. Next door: 20 acres of unkempt forest where bald eagles fly. The pool is closed until end of April and is not heated. The home is warm, unpretentious, with a minimalist approach to décor but a stocked kitchen for those who love to cook. Amenities: a HDTV with premium channels, high speed internet, a ping pong table, lawn croquet and more.

New Private Beachfront panoramic view every window

This luxurious waterfront home has its own private beach exclusive to this property with unmatched panoramic views from almost every room in the house. Perfect for a quiet family getaway where you are looking to just unplug and enjoy the water! This home has everything you need including a fully stocked kitchen, appliances, washer/dryer machines, a screened in porch, 2 open decks off (sunroom & primary suite). Enjoy an evening hanging with the family in the movie room or catch the best sunsets!

Retro Retreat w/ Beaches, Pool + Tennis + Firepit

A quintessential 1970s house, characterized by bold patterns, earthy color schemes, and avocado green appliances. Geometric wallpaper and low-slung furniture dominate the living spaces. Disco-era charm extends to vibrant bedrooms; backyard boasts a lighted firepit area. This nostalgic retreat immerses guests in the groovy aesthetics of the 70s, providing a retro-cool escape. 4 beaches, a pool, and tennis. Close to Westmoreland State Pk, Colonial Beach, art galleries, great restaurants, and more.

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

10/15-18 OPEN Waterfront | Gameroom+Kayak+Firepit

*Ask about our 3+ Night promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Cozy Retreat w/ Pool: MIR & DC

Relax in this spacious 4-bedroom, 1-bath home with a private pool (open May 13th - October 1st) perfect for families or groups. The Maryland International Raceway and Budds Creek Motocross Park are only 7 miles away, making this an ideal spot for race fans...and we have plenty of parking for your race trailers or cars. Washington, D.C. is also just a short drive. With a prime location and plenty of space to unwind, this home offers comfort and convenience for your next getaway.

Year-Round Heated Indoor Pool & Beach Sleeps 16

Make sure you check out the bigger & better version of our property at: www.airbnb.com/h/blackbeard-cottage Welcome to our 5200 sq. ft. 6 bedroom, 11 bed, multi-family beach home on the Potomac River. The 20x60 ft private heated indoor salt water pool, hot tub, kayaks, canoe, paddle boards, fast internet, and more. It's the only waterfront property that's even better in cold weather! Experience the most epic sunrises you've ever seen. This is best river home experience, period.

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Beach Retreat

Relax with the whole family at the Beach Retreat! Enjoy the beautiful Sunrise and Sunsets in the Hot tub overlooking your own private beach! There is plenty to do in the Northern Neck of Virginia! We have Wineries, a Brewery, historical sites, boating, swimming, fires on the beach, bike rides, kayaking, plenty of Summer and Fall Festivals and so many great places to eat on and off the river! The Northern Neck of VA is a hidden gem! Just a 90 minute drive from the DC area

Serenity Bay-Priv Pool-ask about 2-night stays!

Now offering 2-night stays!! Send a message to ask about this! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. Six bedrooms and 5 full baths provide plenty of space for family and friends to enjoy time together. Plenty to do with an outdoor pool, an abundantly equipped recreation room, and a dock from which to launch your kayak or canoe. Easy access to plenty of activities in the surrounding area makes for a memorable vacation.

Waterfront, pool, pickleball

Escape to this luxurious two-story waterfront home with two master suites, sleeping up to 12. Enjoy a gorgeous pool, large decks with scenic views, and a deep-water pier perfect for boating and fishing. Gather around the fire pit or stay active on the private pickleball and tennis court. Inside, spacious living areas offer comfort and style, ideal for families and groups. A serene retreat for relaxation and adventure alike. Book now for an unforgettable waterfront getaway!