Isle of Palms, SC
Rate: $3,164 per night via HomeAway
Reason to book: The third-floor bedroom has a private porch, Jacuzzi tub, and wet bar
Just outside of Charleston, this 10-bedroom/10-bathroom mansion sleeps 28 and takes Southern living to the next level with an elevator, private infinity pool (with built-in hot tub), boardwalk to the beach, and plenty of balconies and terraces to keep you drenched in sunlight. There’s also a massive, sprawling yard should you want to throw some beanbags and/or host a cook-out.
Santa Barbara, CA
Rate: $3,800 per night via Time & Place
Reason to book: A personal concierge can arrange a private chef, restaurant reservations, and more
Encompassing an entire acre of land on its own private cove, this architectural gem rocks everything a high roller and his/her entourage would need: eight-seat theater, walk-in humidor, wine cellar, spa with steam and sauna, and game room complete with pool table and vintage arcade games. Throw in five bedrooms sleeping 10, an outdoor pool, Jacuzzi, fitness center, two sun decks, and the best spot on the beach, and we're talking about the ultimate vacation bachelor(ette) pad.