Vacation rentals with a pool in Diamondhead

Find and book unique homes with a pool on Airbnb

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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Guest favorite
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.
Home in Bay St. Louis
4.95 out of 5 average rating, 112 reviews

Waterfront Comfort With Pool - Sleeps 8!

Waterfront home perfect for a family vacation, fishing getaway, or just for relaxation! Pool & boat launch on premises. Open kitchen/living room floor plan, 3 bedrooms & 2 full bathrooms. The master has a queen bed & en-suite bathroom, the second has one queen bed & the third has a bunk bed w/2 full beds, second full bath in the hallway. Fully stocked kitchen, linens/towels, soap, shampoo, conditioner, coffee & more included. Pets allowed with a $100 pet fee. $30/day fee to use the pool heater.

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
4.98 out of 5 average rating, 151 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.

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, 154 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 from 2nd story balcony. 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 are filled with great shops, restaurants, and museums.

Guest favorite
A waterfront home is depicted, featuring a two-story structure with a red exterior and a spacious deck. The deck overlooks a calm canal with docks on either side. Nearby homes and lush greenery are visible, along with an expansive view of the water extending towards the horizon.
Home in Pass Christian
4.88 out of 5 average rating, 116 reviews

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

Located in prestigious timber ridge community this water front home has it all! A community that features the Pass Christian Isle golf course, a swimming pool, and a large boat launch. Pelican Pass is a 3 bedroom 3 full bathroom home on the canal featuring its own private boat launch/lift and a bonus game room. Enjoy panoramic water views from our spacious deck or from most rooms in the house with fishing right from the on site dock. Each room in the house features brand new smart tvs and

Top guest favorite
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.
Condo in Gulfport
4.99 out of 5 average rating, 117 reviews

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!

Top guest favorite
A spacious elevated home is shown surrounded by trees, featuring a circular above-ground pool and an outdoor seating area with a fire pit. A deck with stairs leads to the entrance, and a grill is visible nearby, creating an inviting outdoor space.
Home in Bay St. Louis
4.93 out of 5 average rating, 126 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.

Top guest favorite
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.
Condo in Long Beach
4.93 out of 5 average rating, 104 reviews

Blue Heaven Condo on the Beach!

Blue Heaven is a cheerful condo steps away from the beach or pool. Come and relax with a cup of coffee while you watch the sun rise over the ocean from the balcony or the front porch. Time slows down at Blue Heaven, no rushing, just full out rest and relaxation. If you prefer retail therapy, dining out, fun at the casino, golfing, biking, ocean tours, chartered fishing - you are in the right place! The Long Beach area is full of options for everyone. Relax, Swim, Enjoy....

Guest favorite
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
4.92 out of 5 average rating, 261 reviews

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.

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, 51 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.

Top guest favorite
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.
Home in Bay St. Louis
4.95 out of 5 average rating, 153 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.

Superhost
Tiny home in Diamondhead
4.75 out of 5 average rating, 12 reviews

Foxtrot Golf Condo at Diamondhead: steps from fun!

Golfers retreat! Perfect for couples and small families looking for a getaway. Steps away from two championship golf courses at Diamondhead Country Club! A quick drive to the beach, marina, fishing and kayaking. Second floor condo overlooking the lake. Our condo is conveniently located at Lakeside Villa’s - a private condo complex featuring owner & guest pools, a pond for fishing, and beautiful live oaks all tucked away next door to The Club at Diamondhead.

Guest favorite
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.
Home in Pass Christian
4.93 out of 5 average rating, 103 reviews

Heated Pool! Petite Retreat in The Pass

The Petite Retreat in The Pass A Serene, Sublime, Self-Contained Vacation Rental The Petite Retreat in The Pass in Pass Christian, Mississippi offers upscale lodging with a heated pool and a full array of amenities to keep the whole family happy without ever leaving the property! Wake up to stunning sunrises over the golf course to the east and enjoy striking sunsets over the bayou to the west. Nature's bounty surrounds this magical home.

Popular amenities for Diamondhead rentals with a pool

When is the best time to visit Diamondhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$17,360 GYDG$18,615 GYDG$19,033 GYDG$17,987 GYDG$17,569 GYDG$19,870 GYDG$19,870 GYDG$17,569 GYDG$17,987 GYDG$23,844 GYDG$20,497 GYDG$20,288 GYD
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Quick stats about vacation rentals with a pool in Diamondhead

  • Total vacation rentals

    Explore 30 vacation rentals in Diamondhead

  • Nightly prices starting at

    Diamondhead vacation rentals start at G$12,549 GYD per night before taxes and fees

  • Verified guest reviews

    Over 870 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Diamondhead vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Diamondhead rentals

  • 4.9 Average rating

    Diamondhead stays are highly rated by guests—averaging 4.9 out of 5!