Rum Cove Vacation Rental; Courtesy of VRBO
All Ages

11 Next-Level Vacation Rentals You Have to See to Believe

See recent posts by Jackie Perrin

We all know that vacation home rentals are a great option for families. But what special features make a rental home-away-from-home a truly luxurious getaway? From amazing pools and over-the-top recreation rooms to themed kids’ bedrooms, special safety features, and proximity to area beaches, theme parks, ski slopes and attractions, these next-level vacation rentals deserve a spot on your bucket list.

Rum Cove Vacation Rental on Anna Maria Island in Florida; Courtesy of VRBO/HomeAway

1. Rum Cove – Anna Maria Island, FL

Swimsuits, flip flops, and a laid-back attitude are practically all you need to pack for a beach vacation at Rum Cove, a 14-bedroom tropical family fun oasis on Florida’s sun-kissed Anna Maria Island,  In addition to paddleboards, kayaks, and a provided golf-cart and bikes for island exploration, Rum Cove offers a resort-style heated waterfall pool, a putting green, multiple lounging areas and a privately owned canal-front dock where you can fish and watch manatee. And did we mention it’s also dog-friendly (with prior approval)? The five-bedroom, six-bathroom rental sleeps 14, and includes two dens with king-size pullout sofas (great for teens) and a crib, a high chair, toys and a shallow pool for little ones. The home is located near popular Pine Avenue, and is a short bike, golf cart or free trolley ride from all parts of the island.

The Castle Vacation Rental in Beaver Creek, Colorado; Courtesy of FlipKey/TripAdvisor

2. The Castle – Beaver Creek, CO

A stunning indoor grotto pool, a movie theater, a great game room and a cozy “cubs den” bunk room for the kids are genuine luxuries at The Castle, a deluxe seven-bedroom, eight-bathroom Beaver Creek, Colorado, vacation rental. However, for many winter warrior parents, what’s truly “grand” about the palatial 14,000-square-foot property are the two amazing amenities practically guaranteed to lighten a snow-weary traveler’s load. You guessed itwe’re talking about personalized concierge service and true ski-in/ski-out access. Your personal concierge can arrange ski and snowboard delivery, purchase lift tickets and book lessons, make reservations and even provide babysitting services. After a fun-filled day on the slopes, you can skip the lines, easily shed and store your gear, and soak your cares away in the rooftop hot tub.

Reunion Villa Vacation Rental at Reunion Resort in Kissimmee, Florida; Courtesy of VRBO

3. Reunion Villa – Kissimmee, FL

If you’re planning a magical trip to Orlando’s theme parks, this six-bedroom, six-bathroom themed rental, located at Reunion Resort, will leave your fantasy fans spellbound. After a day at the parks, they’ll eagerly anticipate swimming in a welcoming waterfall lagoon pool, defending the Force in a Star Wars themed game room and watching favorite films in a luxury 12-seat in-home theater. When it’s time to rest, hand them a ticket to the Hogwarts Express! A Harry Potter-themed bedroom is magically designed for young wizards, with a Diagon Alley sitting area and three enchanting sets of bunk beds.

'Roseanne' Vacation Rental in Breckenridge, Colorado; Courtesy of VillaKey

4. Roseanne – Breckenridge, Colorado

For families with a member on the autism spectrum, the novelties that often go along with travel can present special challenges. “Roseanne,” a five-bedroom, five-bathroom, autism-friendly vacation rental on VillaKey (which specializes in autism-friendly vacation rentals), offers thoughtful comforts that ease the stress of navigating unfamiliar territory. Decorated in muted tones, the Breckenridge, Colorado, home features soft lighting and alarmed exit doors and is cleaned with odor-free products. Convenient to the BreckConnect Gondola, the home is ideally located for a family ski getaway and includes a children’s bedroom with two twin beds, a game room, a hot tub and free Wi-Fi. Ask your friendly hosts about adaptive ski lessons at Breckenridge, and other autism-friendly area programs.

Fortland's Point on the Beach Vacation Rental in Discovery Bay, Jamaica; Courtesy of FlipKey/TripAdvisor

5. Fortland’s Point on the Beach – Discovery Bay, Jamaica

If you often feel like you could use some extra hands while on vacation (what parent doesn’t?), help is on the way at Fortland’s Point on the Beach, a fully staffed seven-bedroom, seven-bathroom vacation rental in Discovery Bay, Jamaica. In addition to a personal chef and two housekeepers, this vacation home rental includes a friendly butler and staff who can help arrange entertainment and excursions. The 3-acre tropical property features an infinity-edge swimming pool with a waterfall, a playground, a putting green, a squash court and three private beaches. Families will find a boatload of extras, including snorkel gear, sea kayaks, games, and a high chair. Missing something? No problem, mon! Your vacation staff is on the job!

Castle by the Sea Vacation Rental in Hilton Head, South Carolina; Courtesy of

6. Castle by the Sea – Hilton Head, SC

Where does a vacationing sleeping beauty slumber? In a Castle by the Sea, of course! Put your young beauties and beaus to bed in royal castle bunks at this seven-bedroom, eight-bathroom Hilton Head luxury home, situated just steps from one of America’s most popular family beaches. Besides super-fun themed quarters for the kids, family-friendly features include a private heated pool with shallow depth perimeter, an elevator, and tons of included kids’ gear. From a crib, baby swing, and high chairs to bed rails, baby gates, a beach wagon and toys, you’ll find virtually everything you need to keep your little ones safe and entertained while on vacation. The grand vacation getaway home is 4,600 square feet and sleeps up to 18 guests.

Oceania Vacation Rental in Stuart Beach, Florida; Courtesy of

7. Oceania – Jensen Beach, FL

Bring your babies, grandparents, and everyone in between (including the dog!) to Oceania, an oceanfront group gathering spot with a treasure-trove of family-friendly amenities! Located on a prime life-guarded sandy stretch on Florida’s Treasure Coast, the eight-bedroom, six-bathroom home features an elevator and virtually every beach toy you can imagine. Besides a fleet of boats and bikesfrom training wheels to teen-readythe home features two kids’ bunk rooms equipped with Xbox and PlayStation systems, a built-in sound system, and a slew of water toys, games and extras, like beach-comber metal detectors for treasure hunting!

Carpe Diem Vacation Rental in Curacao; Courtesy of FlipKey/TripAdvisor

8. Carpe Diem – Wilemstad, Curacao

Curacao is an undiscovered family paradise, and Carpe Diem, a private estate in Willemstad, is the ideal base camp for your next island family vacation! Situated in a private neighborhood, close to beaches and the famous Dolphin Academy, the property is fully gated and features a lovely tropical garden and many thoughtful amenities for little ones. In addition to a specially designed 2-foot-deep baby pool adjacent to the main swimming pool, families will enjoy a private playground and tons of baby and child gear, from safety gates, cribs and high chairs to bouncers and pool toys. A separate apartment—ideal for in-laws—can be rented along with the main house.

Poco a Poco Vacation Rental in Great Exuma, Bahamas; Courtesy of Airbnb

9. Poco a Poco – Great Exuma, Bahamas

Does hauling heaps of special gear take the steam out of your family vacation stamina? Lighten the load when you rent a vacation home with all the water sports equipment you need included! Located beachfront on a calm, secluded cove on beautiful Great Exuma, Bahamas, Poco a Poco is a three-bedroom, two-bathroom Airbnb vacation home rental that includes scuba and snorkel gear, kayaks, paddleboards and fishing poles. While your teens are out snorkeling among nearby coral reefs or exploring the Bonefish Flats by boat, younger kids can splash in shallow waters on the property’s private beach. Poco a Poco features a kid-friendly third bedroom with two twin trundle beds, and an outdoor sea shower.

Dog & Pony Ranch Vacation Rental in Pine Grove, California; Courtesy of HomeAway

10. Dog & Pony Ranch – Pine Grove, CA

An assortment of toys, a swimming hole, plenty of room to romp, and furry friends to play withwhat more does a dog (or kid) desire on vacation? If you can’t leave home without your four-legged family members, the Dog & Pony Ranch should paws-itively be on your family vacation bucket list. Situated in the Sierra foothills in Northern California’s Gold Country, the private vacation rental is located on a 60-acre ranch, and comes complete with use of a dog agility course, a private swimming pond and fully fenced yards where your pups can freely frolic. The 1,700-square-foot rental home sleeps six, and includes a master bedroom, a den with a sleeper sofa (ideal for older kids) and a third-floor loft. Guests enjoy use of a full basketball court, a game room with Ping-Pong, foosball and darts, and many lawn games. You can even interact with the resident farm animals, which include horses, llamas, cows, chickens, and of course, dogs! While welcoming to both dogs and kids, note that the property is not recommended for children under age 5.

Cedar Ridge Vacation Rental Near Nashville; Courtesy of HomeAway/

11. Cedar Ridge – Joelton, TN

Bring the whole family band to Cedar Ridge, a Nashville area vacation rental with everything you need for a rockin’ Music City getaway. Located just 25 minutes from Music Row, the 10-acre, six-bedroom executive estate is especially family-friendly, with amenities you’ll want to sing about. Besides a private in-ground pool, a home theater with a popcorn maker, a playground, a tree house and a kids’ bunk room, the 4,775-square-foot vacation rental features a fully equipped music room, with electric, bass, and acoustic guitars, plus drums, amps, and microphones!

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