Holiday rentals with a pool in Diamondhead

A cozy living area is presented with a light-colored sofa and armchair, complemented by a wooden coffee table. Natural light filters through the blinds, illuminating decorative elements like framed art and stylish mirrors on the wall.

5.0 out of 5 average rating, 90 reviews

Robin’s Nest A Golfers Delight

Welcome to Robin’s Nest located in Molokai Vlg, Diamondhead MS. Golf course, & country club walking distance away. Updated, 1 bdrm condo located on the second floor.Adjustable, queen size bed, guests say is the very “best” and a queen sofa sleeper. 3-4 guests total. Full kitchen,bath with soaking tub. Pool is gorgeous & steps away. Green space, historic oak trees and lots of deer, birds and nature to enjoy! Casinos & Beaches approx 12 min NOLA approx 45 min If shows not avail for a date, msg us

4.99 out of 5 average rating, 141 reviews

A balcony view features two chairs and a small table with a decorative item. The vibrant sunset casts shades of pink and orange over the horizon, creating a serene backdrop against the calm Gulf waters.

Apartment in Gulfport

Gorgeous Oceanview 3BR Luxury Condo - "Latitude"

Welcome to “Latitude”, your dream vacation getaway on the 13th floor of the luxurious Legacy Towers in Gulfport MS. This newly renovated condo includes top-of-the-line finishes and offers breathtaking ocean views that will leave you speechless. Whether it’s waking up every morning and enjoying your coffee while watching the sunrise over the Gulf or relaxing on the balcony while sipping a glass of Champaign witnessing the stunning sunsets, this condo has much to offer and will not disappoint!

4.91 out of 5 average rating, 164 reviews

Pool, Hot Tub, Game Area, Waterfront Bay St. Louis

Relax in this spacious home in Bay St. Louis and enjoy the private pool and hot tub. This home is located on a quiet dead end road and features plenty of space to spread out, relax, and entertain. There is plenty of outdoor seating to enjoy while watching the kids play in the pool, fish from the back yard, or enjoy the fire pit. Cook on the grill and enjoy amenities like the bicycles, beanbag toss, ping pong, beach toys and more. This home is perfect for your next getaway so don't wait.

5.0 out of 5 average rating, 47 reviews

Flat in Diamondhead

Lacey's Coastal Cabana - Charming & Quiet Condo

[Pool access is not available at this time, but pool passes to all other pools are provided] Welcome to Lacey’s Coastal Cabana, the only 1st-floor poolside STR in the complex—dive in anytime! This redesigned 1BR combines the coziness of a weekend getaway with the practicality of extended stays (full-sized kitchen & washer/dryer). 20 mins to sandy shores, 15 to casinos, 45 to NOLA. Golf, tennis, & country club perks are a quick stroll. Stream Hulu, Disney, & ESPN to catch the big game.

4.96 out of 5 average rating, 24 reviews

A patio area features a round black metal table surrounded by four matching chairs. Bright umbrellas provide shade, with one red umbrella prominently positioned. A view of lush greenery is visible beyond the railing, creating an inviting outdoor space.

Townhouse in Diamondhead

Diamond on the Gulf

View sunrises from the front deck, and sunsets from the rear as herds of deer feed just outside. Margaritaville and the George Ohr Pottery Museum are located in nearby Biloxi. Explore a charming former railroad town of Ocean Springs with its shopping and dining district. And it's only a 15-20 minute drive to sandy beaches in Waveland and Bay St Louis from Diamondhead. Free parking is available along the beach road and side streets. Nearby casinos offer seafood buffets throughout the week.

An open-concept studio apartment is showcased, featuring a well-equipped kitchen with white cabinetry and wooden countertops. Natural light fills the space through large windows draped with patterned curtains. The living area includes a comfortable sofa, with a spacious bed visible in the background.

4.87 out of 5 average rating, 53 reviews

"116 On the Green"

116 On the Green is the perfect place for you and your family to enjoy a stay on the desirable Mississippi Gulf Coast. You can step out on the back patio and enjoy your coffee and watch golf as our studio condo sits on the 12th hole. There are two eighteen-hole golf courses and a nearby pool just steps away to enjoy. Bring your appetite and enjoy dinner in or around Bay St. Louis. The beach is only a short drive away and New Orleans is less than one hour away. Located on the first floor!!

Holiday home in Bay St. Louis

Main St BSL: Private Pool & Golf Cart | Sleeps 10

****Now with private heated pool added May 2023**** Welcome to Hidden Paradise on the Bay, a 3 bedroom 2 1/2 bath curated cottage on Main Street in the heart of old town Bay Saint Louis, MS. 2 blocks from the marina and steps away from shopping and restaurants. Take the complimentary golf cart to the beach or for coffee and antiquing, take in a parade or cruising the coast right from the front porch swing. This family friendly home has a private pool and fire pit area for entertaining!

4.95 out of 5 average rating, 107 reviews

4.92 out of 5 average rating, 272 reviews

A well-maintained estate is set on expansive green grounds, featuring a charming two-story house with multiple windows. Towering live oak trees provide shade, and a manicured lawn is adorned with small ornamental plants. A pathway leads from the driveway to the inviting property entrance.

Bungalow in Long Beach

Shell House Estate Bungalow

We are located on the Gulf of Mexico. A private beach is out your front door along with Fishing and Sailing. We are also a short distance from Casinos, as well as many family-friendly activities. This is a three acre 170 year old private estate property with 500 year old registered live oak trees. The Bungalow also has a covered parking space. THE POOL HOUSE sleeps 6 two in one room and 4 in the other room. BUNGALOW sleeps 4 two in one room and 2 in the other room. See photos.

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.

4.92 out of 5 average rating, 59 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.

The charming beach house is surrounded by lush greenery and features a well-maintained garden area. A gravel path leads to the entrance, with welcoming steps leading up to a covered porch adorned with ceiling fans. A picket fence encloses the inviting front yard.

4.99 out of 5 average rating, 109 reviews

Beach Bungalow - Private Pool+Walk to Town & Beach

Uniquely sophisticated and charmingly luxurious beach house with a private saltwater pool in Bay St. Louis' Historic District. Experience all that Bay St. Louis has to offer from this cozy, beautifully appointed bungalow located 1/2 a block from the beach and walkable to a vibrant downtown. Located about a 30 minute drive to Stennis Space Center and less than an hour drive to New Orleans. Across the Bay Bridge, discover neighboring towns of Mississippi’s “Secret Coast".

A shaded outdoor lounge area is featured, furnished with a dark sectional sofa adorned with red cushions. A coffee table is placed centrally, accompanied by a bottle of wine and a floral arrangement. The background showcases a private pool surrounded by greenery.

4.96 out of 5 average rating, 169 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.

4.84 out of 5 average rating, 134 reviews

The exterior of the multi-level house features a private pool surrounded by a safety fence. A shaded seating area and outdoor dining space are visible beneath the house, with green grass extending around the property. Tall trees provide natural shade and enhance the outdoor space.

Home in Waveland

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.

Popular amenities for Diamondhead rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A heated saltwater pool is framed by lounge chairs and an umbrella, and a fire pit with a glass top sits nearby, producing a warm glow. Soft lighting illuminates the surrounding area, creating a relaxed outdoor setting that encourages leisurely gatherings.

4.99 out of 5 average rating, 113 reviews

Spencer's Way Beach House B with heated pool

A spacious vacation home is set within a natural landscape, featuring a fenced heated pool. Umbrellas provide shade around the pool area, while palm trees frame the exterior. The home's multiple decks overlook the surrounding greenery and can be accessed via outdoor stairs.

4.94 out of 5 average rating, 113 reviews

Heated Pool! Petite Retreat in The Pass

A waterfront home is shown, featuring a spacious deck and a private boat launch. The structure is positioned alongside a canal, with neighboring homes visible in the background. The calm water reflects the clear blue sky above.

4.89 out of 5 average rating, 127 reviews

*Pelican Pass* Golf/Fish/Swim / Incredible water v

An inviting outdoor space features a sparkling pool surrounded by lounge chairs and shaded areas. A hot tub sits nearby beside a tropical-inspired backdrop with palm trees and wooden seating. The bright blue sky is dotted with fluffy clouds, enhancing the serene atmosphere.

4.91 out of 5 average rating, 154 reviews

Family Home "Lone Star Cabana" Shared Pool!

A wooden deck surrounds a pool, framed by railing and offering a view of the waterway. In the background, a light-colored two-story home with a metal roof is visible under a clear blue sky.

4.95 out of 5 average rating, 114 reviews

Waterfront Comfort With Pool - Sleeps 8!

A spacious front porch features several white rocking chairs that face the waterfront, offering views of the serene bay. Lush greenery is visible in the surrounding area, while the walkway leads toward a scenic road by the water.

4.96 out of 5 average rating, 105 reviews

Southern Charm-Beach Front BSL with Saltwater Pool

5.0 out of 5 average rating, 28 reviews

Henley House - Enjoy Pool, Old Town or Beach

5.0 out of 5 average rating, 33 reviews

The View | Waterfront • Pool • Paradise •Golf Cart

Apartment rentals with a pool

4.92 out of 5 average rating, 122 reviews

The living area features a spacious white sectional sofa adorned with blue accent pillows. A dining table with chairs is positioned nearby, complemented by light fixtures overhead. The backdrop consists of a kitchen visible in the distance, with white cabinetry and appliances.

Apartment in Long Beach

Blue Heaven Condo on the Beach!

4.97 out of 5 average rating, 163 reviews

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.

Apartment in Long Beach

Beautiful Long Beach Condo with Ocean View+Pool!

4.85 out of 5 average rating, 297 reviews

Beach Getaway

4.8 out of 5 average rating, 160 reviews

Biloxi Beach Condo @ 2046 Beach Blvd, Biloxi

4.92 out of 5 average rating, 136 reviews

Sunny Beachfront Biloxi Condo w/ Resort Amenities!

4.97 out of 5 average rating, 261 reviews

Contemporary Biloxi Condo for 2 - Oak Shores

The studio features a spacious bed with a decorative headboard, complemented by two pillows and a neutral-toned blanket. A small seating area with two upholstered armchairs is situated nearby, while natural light filters in through a window adorned with blinds.

4.91 out of 5 average rating, 176 reviews

The Ritz

A spacious studio area features a large bed with striped bedding and a flat-screen TV mounted on the wall opposite. Light-colored furniture, including a storage cabinet and small dining table with two chairs, complements the room. The kitchen area is visible in the background, highlighting cabinets and appliances.

4.94 out of 5 average rating, 262 reviews

Beautiful Biloxi Getaway Beach Condo!

Other holiday rentals with a pool

5.0 out of 5 average rating, 3 reviews

No Stairs! 2 Bedroom Condo at the #12 Pine Green!

Holiday home in Bay St. Louis

Pool & Spa - Luxury Retreat With Bay Views

4.98 out of 5 average rating, 42 reviews

5.0 out of 5 average rating, 42 reviews

Vibez on the Lanai | Poolside Golf Course Retreat

4.89 out of 5 average rating, 35 reviews

A cottage is set in a spacious outdoor area, surrounded by greenery. The screened-in porch is visible, providing a shaded space. The white exterior of the cottage contrasts with the natural surroundings, while bushes line the path leading to the entrance.

Cabin in Bay St. Louis

Cottage At The Campground

A comfortable living area is presented with a beige sofa and a plush armchair, accompanied by a round dining table with four white chairs. Natural light filters through a window, illuminating decorative wall art and enhancing the inviting ambiance.

4.94 out of 5 average rating, 34 reviews

1BR/1BA w/POOL & Golf - Sunshine Oaks

A spacious bedroom is furnished with a light wood bed frame, plush bedding, and decorative pillows. A large window allows natural light to brighten the room, complemented by elegant wall decor. The living area showcases a sectional sofa, glass coffee table, and large windows framing views of the outdoor space.

4.97 out of 5 average rating, 32 reviews

Tranquility Bay Cottage

An outdoor seating area is presented with comfortable furniture, including a coffee table and cushioned chairs. A television is mounted behind open shutters, and a stack of firewood is stored nearby. The setting is shaded and features light-colored walls, creating a relaxing atmosphere.

4.85 out of 5 average rating, 20 reviews

Fabulous Waterfront Getaway!