The 11 Most Ridiculous Beachfront Vacation Rentals in America

Published On 08/07/2015 Published On 08/07/2015

With summer officially in session, it’s time to round up the crew for some serious beach action. But checking into an oceanfront resort can have a lot of drawbacks: screaming kids crammed in the communal pool, exorbitant high-season rates for tiny rooms, and hotel security all up in your grill for late-night antics (we trust you won’t always be on your best behavior).
Enter: the vacation rental. They’re affordable, offer more privacy, and aren't just for families anymore. But not all beach vacation rentals are created equal; in fact, some of them are so over the top you’ll want to stash an extra set of keys in your bag when you take off at the end of the week. These are 11 of those spots.

Resort Realty/

Drop Anchor Estate in Kill Devil Hills

Kill Devil Hills, NC
Rate: $5,895 per week at HomeAway
Reason to book: Indoor wet bar, downstairs bar, outdoor cabana bar, you get the idea
Kill Devil Hills is unarguably one of the best surfing spots on the East Coast, and Drop Anchor is the vacation rental throne for surf crews. The 16-bed/16-bath nautical-themed estate sleeps a whopping 40 guests and has its own boardwalk that leads directly the beach. It’s also seemingly built with the dude in mind (although not THE Dude, just guys in general): there’s a pool table, poker table, foosball table, private heated pool, and home theater.

Ocean Villa in Malibu

Malibu, CA
Rate: $5,000 per night via Luxury Retreats
Reason to book: The outdoor fireplace, in-room treadmill, and the oceanfront hot tub and rock sauna
Can’t afford a multi-million-dollar home on a Malibu beach like Larry Ellison, Dustin Hoffman, or Goldie Hawn? Live vicariously like an A-lister for the week in this six-bedroom, six-bathroom ocean villa right smack on a private, gated beach. The bi-level, Cape Cod-style house is unapologetically sunny and cheerful, with ceiling skylights and patios aplenty.

Kauhale Pilialoa

Big Island, HI
Rate: $13,125 per night via VRBO
Reason to book: For a nominal fee, tenants can use the neighboring resorts’ facilities, including tennis courts, golf, and pools
Sometimes you just need a dramatic cliff in your backyard. The Kauhale Pilialoha Estate in Big Island, Hawaii, is perched right along the Low Bluffs, flanked by two of the island’s best beaches, Mauna Kea and Hapuna Beach. Its 2.5 acres are filled with koi ponds, a game room, open-air lounge and bar, massive lanai, outdoor BBQ, infinity pool, and 10 bedrooms for your 30-person crew.

Laguna Beach realness

Laguna Beach, CA
Rate: $5,500 per night via HomeAway
Reason to book: Skylights and hot tubs
A short drive from Los Angeles and San Diego, Laguna Beach has served as a highbrow getaway for decades. Most visitors shack up at five-star resorts like Montage Laguna Beach and St. Regis Monarch Beach, but privacy seekers make a beeline to any number of over-the-top vacation rentals like this property. With direct access to Wood's Cove Beach, the three-bedroom villa sleeps eight and is a favorite of the art and design set with its modular facade, intuitive architecture, and mod interior design that blends with the destination.

Redondo Beach ridiculousness

Redondo Beach, CA
Rate: $3,075 per night via Luxury Retreats
Reason to book: The private, outdoor basketball court
Those outside LA may not know this tiny sliver of paradise just a few miles from Santa Monica, but it’s the stomping ground for professional athletes and celebrities, and home to some million-dollar homes. This 7,800sqft, seven-bedroom villa is tricked out with an outdoor pool (with illuminated waterfalls and a water slide!!), marble fireplaces, grand piano, private theater, a dry sauna, and pool table.

Belle Mer Mansion

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 Beach Club

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.


Palazzo Del Mar

Destin, FL
Rate: $5,740 per night via Airbnb
Reason to book: Ummm, there's an elevator that visits all four floors, as well as a dumbwaiter to carry late-night snacks from the kitchen to the second floor
Destin, Florida, isn’t exactly luxury hotel central, so Palazzo Del Mar is the next best thing. This gated Mediterranean-inspired estate sleeps up to 25 guests in 11 bedrooms (and separate guest cottage) and is located literally on the shore of the Emerald Coast. It boasts an outdoor pool, private access to the beach, and spectacular sunrise and sunset views.

Villas at Ritz-Carlton Reserve, Dorado Beach

Dorado Beach, Puerto Rico
Rate: $10,000 per night
Reason to book: The ability to order the resort’s room service, as well as cocktails created by the in-house, award-winning mixologist
Ritz-Carlton Reserve, Dorado Beach is one of the newest, most luxury-drenched resorts to open in Puerto Rico, and not a lot of people know that the Bill Bensley-designed property manages two, five-bedroom villa vacation rentals. What exactly does one of these slices of heaven get you? Your own private infinity pool just steps from the ocean, floor-to-ceiling sliding-glass walls, a fully equipped kitchen, a 24-hour butler, and access to a Jose Andres restaurant and rainforest spa.


Montauk Compound

Montauk, NY
Rate: $2,250 per night via Airbnb
Reason to book: The private staircase leading down to the exclusive beach
This charming zen retreat is all about tapping into your holistic side with the relaxing koi pond, Balinese meditation platform, and sweeping, stress-busting views. The private estate immersed in nature sleeps eight in four bedrooms and includes an outdoor shower, Ping-Pong table, and personal golf cart.

Wailea Beach Villas

Maui, HI
Rate: $1,460 per night via Destination Resorts
Reason to book: Private adult pool and hot tub
Tell anyone in Maui you’re staying at Wailea Beach Villas, and they’ll likely throw you shade envy. The vacation rental managed by Destination Resorts is the most luxurious crash pad in Wailea, a resort area known for its upscale properties like Four Seasons, Andaz, and Waldorf Astoria. The lowest-tier accommodation is a two-bedroom penthouse suite, and all villas are equipped with outdoor terraces, sliding floor-to-ceiling glass walls, modern BBQs, fully equipped kitchens, washer/dryer, and bathrooms the size of an NYC studio apartment. But the biggest luxury is the privacy, as there are only 100 villas sprawled across five tropical acres of lush foliage, waterfalls, and Tiki torch-lit ponds.
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