Vacation rentals with a pool in Diamondhead

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Top-rated rentals with a pool in Diamondhead

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

The exterior of Henley House is framed by a large, mature tree, providing ample shade. The home features a light-colored facade with a welcoming front door and multiple windows that allow natural light. A green lawn surrounds the property, emphasizing the tranquil setting.

Home in Bay St. Louis

4.98 out of 5 average rating, 104 reviews

Henley House - Enjoy Pool, Old Town or Beach

Enjoy coastal living in the quaint town of Bay St. Louis. Visit the beach (half a mile) or spend the day in the private pool. Henley House offers three bedrooms, a guest bath, along with a spa-like master bath. We provide you with a well stocked kitchen, fully stocked bathrooms, WIFI and smart TV in living room and bunk room. Come prepared to swim in the newly renovated pool (not heated), with a tiki bar, grill, and outdoor bath and shower. Close to Old Town; near boutique shops and restaurants.

Top guest favorite

A clear view of a swimming pool surrounded by a textured concrete deck and loungers. Two-story buildings with balconies are visible in the background, framed by palm trees. An umbrella provides shade over a table set for outdoor seating.

Condo in Biloxi

4.97 out of 5 average rating, 247 reviews

Contemporary Biloxi Condo for 2 - Oak Shores

Welcome to this beautifully renovated condo in the Biloxi Oak Shores complex. Luxury amenities include a gorgeous bathroom, a gourmet stainless steel granite kitchen, luxurious bedding, and a 50-inch TV. Enjoy TV with Sling, Roku, or use one of the apps the smart TV provides. You will be surrounded by a carefully curated mix of bespoke antiques from Europe, modern and custom furnishings, and eclectic original artwork. Please note a 2-person max occupancy. Exterior cameras present. None inside

Top guest favorite

A heated saltwater pool is surrounded by a spacious deck, illuminated by soft outdoor lighting. Comfortable lounge chairs line the poolside, while a table with colorful seating is positioned nearby. A fire feature adds warmth to the space, creating a cozy gathering area.

Home in Bay St. Louis

4.99 out of 5 average rating, 140 reviews

Spencer’s Way Beach House A with heated pool

Come and relax with the family at our newly constructed beach themed home. Blocks away from the center of Bay St. Louis and the beach. The Bay has a small little city Key West vibe , with boutiques, antique shops, great restaurants with live music. We Invite you to stay at our cozy Place and have a wonderful time. There is also a new HEATED salt water pool with barbecue area, fridge & sink. Bar area with television and blue tooth speakers for your enjoyment. The pool is shared by both units.

Guest favorite

A studio space is displayed with a spacious bed featuring striped linens. A wooden dresser and small television are positioned against one wall. Two lamps offer soft lighting beside the bed. A nautical wheel decorates the wall, complementing the light blue curtains and seating options in the room.

Condo in Biloxi

4.85 out of 5 average rating, 257 reviews

Beach Getaway

Full studio (388 sf) near Keesler, across from the beach, restaurants, and shopping. There is a public bus stop on the corner & shuttles for the casinos. Wifi with small smart TV. Let yourself in with keyless entry then go for a swim, enjoy coast seafood, or join the excitement at a casino. Make yourself at home and feel safe with security lighting and no stairs. My place is good for couples and solo adventurers. No trailer parking allowed. Max. occupancy is 2: violation results in eviction.

Guest favorite

A two-story beach home stands amongst mature trees, featuring a large driveway leading to its elevated porch. The exterior presents a combination of white and blue, with multiple windows allowing for natural light. Lush greenery surrounds the property, providing a serene environment.

Home in Long Beach

4.9 out of 5 average rating, 175 reviews

Gulf Moon II - Spacious Beachfront Home with Pool

Beautiful two-story home located on the sandy beaches of the Mississippi Gulf Coast. Boasting a large pool, gated backyard, and spacious pergola, this beachfront home is the perfect spot to host your next getaway! Enjoy unobstructed views of the calm Gulf waters or take the short 50-yard walk to put your toes in the sand. Positioned directly on Beach Blvd in cozy Long Beach, you'll be only minutes away from some of the finest restaurants, cafes, bars, and shops that the coast has to offer!

Top guest favorite

An open living area is presented with a spacious sofa and coordinating armchairs. Large windows invite natural light, complementing the light-colored walls and tiled flooring. A dining table with chairs is visible, alongside a kitchen area featuring a coastal-inspired design.

Condo in Long Beach

4.97 out of 5 average rating, 151 reviews

Beautiful Long Beach Condo with Ocean View+Pool!

Pristine condo right on Beach Blvd. Grab your flip flops and walk across the street to the beach and enjoy the beautiful sunsets. Stainless steel appliances, granite counter tops, and Flat Screens in each room. Our condo has a beautiful beach view. Long Beach is the hidden gem of the Mississippi Gulf Coast. Hop in the car and visit the sights in Gulfport, Biloxi, Ocean Springs, Pass Christian, and Bay St Louis. All of these towns are filled with great shops, restaurants, and museums.

Top guest favorite

A pool area is highlighted by a clear blue swimming pool, surrounded by a concrete deck. Patio tables with umbrellas are positioned nearby, offering shaded seating options. Two-story condominium units are visible in the background, framed by lush greenery and a clear sky.

Condo in Biloxi

4.99 out of 5 average rating, 151 reviews

Come and "Stay Awhile" at Oak Shores

Come "Stay Awhile" at my beautifully updated condominium. I am located directly across the street from beautiful Biloxi Beach. I am centrally located within minutes of several 5-star casinos, including the Beau Rivage and Hard Rock . The entertainment and dining options are endless. After a busy day, you can return to enjoy the 2 beautifully updated pools on property and cook a delicious meal in my fully stocked kitchen. You will love visiting Biloxi as much as I love living here!

Top guest favorite

A cozy living area features a gray sofa adorned with turquoise cushions. Two white wicker chairs with blue accents provide additional seating. A round, white coffee table with a small plant centers the space. Three landscape photographs hang above the sofa, enhancing the ambiance.

Condo in Diamondhead

4.92 out of 5 average rating, 37 reviews

Beautiful condo on Golf Course

Relax with the whole family for a fun yet relaxing getaway. This gorgeous second floor condo overlooks a crystal clean pool and is walking distance to Diamondhead country club which features a golf course, tennis, pickleball, swimming and restaurants. And, if you need to get a little work done during your stay, there’s a desk and comfortable work chair with a great view of the pool and garden area. You’ll be close beaches, casinos and other fun activities during your stay.

Guest favorite

A peaceful private pool is surrounded by a wooden fence, adorned with potted plants. Gentle water flows from a feature fountain into the vibrant blue water, reflecting sunlight. Comfortable lounge spots are available around the deck for relaxation.

Home in Bay St. Louis

4.95 out of 5 average rating, 144 reviews

Private Pool, One minute to Beaches!

Experience the charm of Old Town Bay St. Louis, just a short 5 minutes away! Indulge in the delights of local restaurants, boutique shopping, thrilling fishing adventures, and so much more! Indulge in our fully equipped kitchen, lounge by the pool, and BBQ in your private oasis. Rest soundly in our cozy beds. Book now for the ultimate getaway! Don't miss out on this unforgettable experience! Book now and secure your slice of paradise! Your dream getaway awaits.

Guest favorite

An aerial view displays the condo complex nestled among mature trees, with a tranquil lake nearby reflecting the greenery. The scene includes a pool area, surrounded by nature, and hints of the golf course in the distance, highlighting the serene environment.

Tiny home in Diamondhead

4.88 out of 5 average rating, 60 reviews

UnForeGettable 19th Hole Golf Course Condo-pets ok

Steps away from the Country Club and 36 holes of golf! Remodeled & updated 2nd floor condo overlooking the lake at Lakeside Villas. Our studio condo offers sleeping for 4 with a full kitchen, fireplace, & smart TV in a cozy, bright environment. The covered back porch is the perfect place to unwind after a day of golf or relax at the pool by the lake. Mature oaks, park like setting. The complex is next door to the Clubhouse & Grill+Bar. Fan favorite property!

Guest favorite

An outdoor heated pool features clear, inviting water, surrounded by wooden decking. Sunlight reflects off the surface, while green trees and a view of the river are visible in the background, offering a tranquil setting for relaxation.

Home in Pass Christian

4.95 out of 5 average rating, 151 reviews

Reduced AUG/SEP Pool, Hot Tub, Boat/Fish Dock

Isolated Riverfront on 3 acre estate overlooking the Wolf river. Hot tub. Heated Pool. No pet fees. We answer inquiries IMMEDIALTLY. Fish or park your boat in the back yard. Free boat launch is one mile west. Managed by owners who live nearby. Open ten years. Check our reviews and review scores. 16 Guests is an AIRBNB advertising limit. We have a limit of 30 overnight guests but have beds for 18. Floor mattresses available.

Superhost

A private pool is set in a well-maintained outdoor space, surrounded by green grass. Comfortable lounge chairs sit beside the pool, accompanied by a fire pit. The structure showcases a raised deck with a seating area, blending seamlessly with the surrounding nature.

Vacation home in Waveland

4.83 out of 5 average rating, 109 reviews

Coastal Oasis - Heated Pool, Walk to Beach!

Bring the whole family to enjoy a beach vacation on beautiful MS Coast. Just 5 minutes to the shops and restaurants in downtown Bay St. Louis, the West Inn Beach club is it's own private oasis. 3 blocks to beach, private pool, ping pong, outdoor living room/tv, yard games, 600 sq ft. of screened in porches. Sleeps 12! We offer the pool to be heated November - March for an additional fee. Please inquire.