Holiday rentals in Watersound

New Beginnings-Private Beach, Resort Pool 4 Bikes

Indulge in a luxurious coastal escape at "New Beginnings," a beautifully updated 3-bedroom, 3-bathroom retreat nestled within the exclusive Watersound West Beach community. This exquisite home offers the perfect blend of comfort and convenience, featuring open-concept living, a private outdoor patio, and access to a stunning resort-style community pool. Whether you're exploring the scenic trails on the four complimentary bikes or lounging on the sugar-white sands via the private boardwalk, this

Heaven on 30a by Stay on 30a

Running to the store after check-in isn’t a vacation. Two nights in and you’re rationing toilet paper like it’s a reality show.. ✨ We fixed that. With Stay on 30A, every stay is designed to feel effortless from start to finish. 🚲 FREE luxury bikes 🏖️ Easy beach access + resort-style pools 🧴 Full-size amenities (no starter kits) 🧹 Arrival inspections + meticulous cleans 📞 24/7 local support ⚡ Rapid-response maintenance & care We host our stays the way we’d want our own vacation to feel.

NEW rental on 30A near Rosemary w/Golf Cart

Rosé All Day on 30A is a BRAND-NEW rental located on 30A in Watersound, FL, between Seaside and Rosemary Beach across from The Big Chill. This luxurious 2-bedroom 2-bathroom townhome is a completely NEW rental. Tons of new items have been added to this NEW listing, and a complimentary welcome bottle of wine and glasses will be waiting for you upon your arrival/plus movie night popcorn and candy! As a bonus, a 6-seater golf cart is available to use free of charge during your stay.

Prominence 30A: Golf Cart, Bikes, Pool

Southern Bliss has the sophistication of a modern beach house with a coastal vibe. This 3B/2.5B home is a short walk to the resort style pool and The Big Chill (aka The Hub) to enjoy restaurants, shops, shows, movie nights and concerts. Minutes to the beach using the golf cart or bikes provided is an added bonus! This stunning home will guarantee your vacation needs are met. Enjoy the fully equipped kitchen, new furniture/decor, comfortable beds, beach gear, and washer/dryer!

Summer Fun on 30A | Bikes, Bunks + Beach Days

Experience an unforgettable tropical holiday in this charming townhouse in Prominence North on 30A. Its bright, open interiors and two bedrooms are ideal for smaller families or a couple's getaway. Tastefully decorated with a coastal ambiance, this luxury townhome offers a carefree and relaxing atmosphere! The 5,000 square foot community pool and "The Big Chill" (formerly known as "The Hub"), a lively entertainment, shopping, and dining mecca, are both within an easy walk.

Prominence 30A "Sand By Me" 4BR/4.5BA - Sleeps 12

Sand By Me offers one of the very best family beach vacations along Florida's Emerald Coast. Located in the community of Prominence, a short bike ride to the sugar white sands of 30A. Relax on one of four spacious porches. This newly constructed open floor plan home has 4 bedrooms, 4.5 baths, sleeps 14 and includes two master suites, a kids bunk room, a king guest room, and a flex space with memory foam queen sofa bed. Golf cart rental available for an additional fee.

Prominence Salt & Light - Townhouse w/Golf Cart

Prominence Salt & Light Watersound, Florida - Newly Listed Welcome to Salt & Light, a stylish 2-bedroom, 2-bathroom vacation home in the heart of Prominence on 30A—one of the most sought-after communities along Florida’s Emerald Coast. This beautifully appointed retreat offers all the comforts of home, plus premium perks like a 6-seater golf cart, seasonally heated pool, and walking distance to the Big Chill.

Sea.Away | 30A | Between Rosemary & Alys Beach!

Nestled between Rosemary Beach + Alys Beach, Sea.Away is your ideal getaway location. The 3 bedroom, 3 bath home features a newly renovated upper deck with partial ocean views, a lower patio with outdoor grill and shower, and gated front door parking. No need for a golf cart or shuttle in this gated community, as the Gulf’s sugar sands and private community pool are a 1 minute walk from the front door!

Prominence, The Big Chill! 2 Pools! 4 Bikes!

Welcome to Prominence Paradise, a modern 2 bedroom, 2 bathroom townhome in the heart of 30A! Perfectly located next to The Big Chill, this stylish escape features resort-style pools, 4 bikes, a gourmet kitchen, and a spacious covered porch. Enjoy local dining, trails, and beach days via the seasonal shuttle or nearby access points. Sleeps 6 and ideal for couples, small families, or a friends' trip!

Sea La Vie

This stunning townhouse is located directly beside the neighborhood pool, providing an easy transition from the until to the pool. It is a quick walk across the street to the Big Chill, where there is family friendly entertainment, restaurants and shops. Prominence is centrally located between public beaches, providing convenient access with just a quick bike ride or drive.

Bikes | 2 Pools | Near The Big Chill

White Sand Dreamin' - Experience luxury in this 2-bedroom retreat situated in the Prominence community on 30A! You'll fall in love with the home's proximity to the resort - style 5000 sq ft pool, popular 'The Big Chill', and minutes to the beach! Home features - open concept living, bikes, and complimentary beach gear. Sleeps 6! The Prominence community is a gem!

Resort Pool + Cart | Steps to Big Chill on 30A

Welcome to Beach Era, your chic 2-bedroom retreat in Prominence on 30A. Enjoy effortless access to the sugar-white beaches, the resort-style pool, and The Big Chill’s shops, dining, and live entertainment just across the street. With a golf cart, 4 bikes, beach gear, and a spacious balcony near the pool, Beach Era offers the perfect coastal escape.