Most Luxurious Caribbean Island Vacations for 2014

We traveled the Caribbean,  read reviews,  talked to travelers,  drank many beach cocktails,  walked many sandy beaches, all for the sole purpose of uncovering what may just be the ultimate list of vacation rentals in the Caribbean. Yes, it was rough but as they say …. “someones goto do it.”

These choices are not based on affordability, in fact all are ultra-luxurious.  They aren’t based on being quirky and weird either.

These accommodations offer the ultimate in luxury, amenities and service – in many instances rivaling and exceeding the services offered by the world’s most exclusive hotels.  Hyperbole? We think not.

How many hotels have a full-time staff catering to the needs and whims of one party, one one island, for an entire week, month or year?

The List

Caneel Bay, USVI

There may be no finer antidote to over stressed life than an escape to this gorgeous place. Caneel Bay is a tech-free ethos and a sanctuary to life.

Over Yonder Cay,  Exuma Chain, Bahamas

Over Yonder Cay welcomes you and 27 other guests, in four villas and is best described as a unique private haven for people seeking an authentic,  barefoot luxury experience.

Peter Island,  British Virgin Islands


Peter Island is the ultimate in island fantasies. This tropical island paradise may be reserved exclusively for you and your selected guests.

Guana Island, British Virgin Islands

Guana Island may just be the Garden of Eden. A lush, tropical oasis, Guana Island spans 850 acres, of undisturbed natural beauty and it can be all yours, with cocktails,  umbrellas and snorkeling gear.

 Caya Espanto, Belize

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The ultimate resort experience on your own private island. Casa Espanto offers you your own island paradise, total privacy and 5 star resort amenities.  It is  a place where paradise and luxury come together for the ideal Caribbean getaway. This place was especially created for travelers looking for the best that life has to offer.

Fowl Cay, the Bahamas

Enjoy a casual, carefree environment. Swing like a castaway in one of the hammocks, walk one of the beautiful beaches, while enjoying unrivaled tranquility. Then after your day is over, allow the sounds of ocean waves to lull you to sleep.   The team at Fowl Cay deliver the ideal blend of a vacation home experience combined with a full service resort.

These vacation opportunities and others can be found as part of VacationDigg’s Private Island Collection.

Your African Escape : Into the Wild

The Great Rift Valley, that cuts through Northern Kenya, in a series of mazy peaks and depressions, is home to some of the most magical scenery found the world over.   It’s also home to Kamogi  – a low key, and really laid back private ranch,  that is an ideal spot for travelers who are looking to truly experience the African wild.


A ramshackle and enchanting property,  it’s a very much loved family home, whose owners have opened their doors for guests to experience a “slice of life” on a private ranch in Africa.


The feel here is beautiful, totally wild and very much “at home.”  You’re yards away from the Il Pinguan lugga – seasonal river bed –  that traverses the Laikipia plateau, for 100 miles, before feeding into the Ewaso Ngiro River. The Il Pinguan acts as a water access point for the ecosystem that includes 200 year old acacia forests, herds of buffalo, elephant, gazelles as well as their predators the lions, leopards and cheetahs.  This makes it it one of the best places in Africa to experience the wild, magic of this exceptional land.


This isn’t your resort stay, with fences around the pool and property.   Though you have a pool and a tennis court, this is Africa for real.  Here you’re in the WILD.  It’s open and fenceless and the wildlife you see is conducting its everyday life  – and there’s no lack of it!  Every minute is exciting,  as you have no clue what you’ll see next.


This is the African wild.  It’s a place that will rejuvenate your senses and emotions.   For the faint hearted,  its worth knowing that there is 24-7 security in case of wayward lions.


So if you’re ready for a trip of a lifetime visit Pinguan House.


Call of the Slopes : It’s Good to be on Top at Steamboat Springs



















For a winter vacation home you simply cannot find a better location in Steamboat than his ultra-luxurious and amenity packed home.   When you’re here, you’ll be right on the mountain and directly on the slopes,  in an uncluttered spot, with extensive and stunning views of Steamboat Springs.

Want to hit the slopes?  This magnificent home is a true a ski-in/ski out accommodation and it’s large enough so that when you return home and want to relax you’ll be able to hang out in one of the large living room areas or find a quiet spot, next to a fire place, and unwind with a book and a glass of your favorite apres-ski cocktail.

The interior has been designed and furnished by TRH Interiors, the designers who have designed several of the Ritz Carlton’s iconic hotels.   The result is  sophisticated comfort that exudes both a feeling of warmth and elegance.

Traveling with a large family and friends?   There’s plenty of space for for up to  14 guests to enjoy, this one-of-a-kind vacation spot,  in its 3 lavishly decorated living rooms,  several outdoor decks, game room with full bar and indoor basketball court.     Ready to hit the slopes @Steamboat? Yes

Wondering if Steamboat Springs is the “right” ski or resort for you?

Lake Tahoe in Luxury

Lake Tahoe is exquisite and we’ve discovered one of the Lake’s most fabulous homes.


Named NINETEEN SEVENTY, this unreal vacation home is located in West Lake Tahoe, California, and offers vacationers over 12,000 square feet of glamorous,  yet relaxed lakefront living.


And for water lovers,  NINETEEN SEVENTY’s 145 foot pier features one of the few cribbed slips on the lake, providing the perfect platform for boating, swimming, and other water sports.


This home is the ideal, luxurious lake getaway for families and friends.  Featuring 9 bedrooms you’ll find plenty of room for socializing and when you’re ready for some R&R you’ll be certain to find a quiet spot, overlooking the lake, where you can chill out and take in the beauty of this fabulous vacation spot. The one and a half acres of landscaped grounds include a children’s playground and a 1,200 square foot Guest House.


In the Main Home, there is a grand living room with soaring ceilings, a massive wood-burning fireplace and a stunning wall of glass that frames the lake and the mountains beyond. French doors from the living room and family room lead to the deck which is furnished with built-in Viking outdoor gas grills and comfortable outdoor furniture. The kitchen is a gourmet’s delight with the latest appliances and a spacious layout which allows for several chefs to work simultaneously. Adjacent to the kitchen, the family room has its own wood-burning fireplace, a full bar and over-scaled, comfortable furniture.


The house comes with movie theater, a billiard room and a fully equipped fitness center. When work summons, the wood paneled office provides an elegant oasis with a gas fireplace and striking lake views. Down the stairs from the dining room is a spacious wine cellar and tasting room. The master suite with its dramatic ceilings and windows has a fireplace that warms both the bath and the bed area. From the serenity of the freestanding bath, you can survey the ever changing lake. The west suite is a fully enclosed room with its own complete kitchen, bathroom and petite balcony. In all, the Main Home has seven bedrooms and eight bathrooms. The kitchen and bars are stocked with wine, beer and other beverages.


The detached two-story Guest House includes a small but complete kitchen and a comfortable living room with a full height stone hearth and gas fireplace. It has two bedrooms and two bathrooms. Winter is magical at NINETEEN SEVENTY. Radiant heat keeps the house warm at all times. Sit by a roaring fire in front of one of the property’s six fireplaces and watch the snow fall on the lake. The driveway has a snow melt system so getting to the nearby ski resorts is never a problem.


The property is conveniently located between Tahoe City and Homewood providing many excellent options for dining and shopping.


Best of all, you can walk right out of the front gate to nearby restaurants, playgrounds and a market.


In the winter, world-class ski slopes are 15 minutes away. If you wish to try your luck at gambling, South Lake Tahoe is near enough for access via road or water.


          Ready to getaway visit the
           website to reserve your winter spot today.

Vacation Rentals and Hotels Pros and Cons

An interesting on planning a family vacation and what are the pros and cons of a hotel compared to staying at a vacation rental.
Your Family Vacation Planner


For a great selection of vacation rentals check out  If you need assistance booking a vacation rental please contact us at VacationDiggs and we will be happy to assist you with the process.   Vacation rentals will more than often provide you with much more space and many additional amenities not found in a hotel room and for far less per person.

10 Reasons Why You Should Stay in a Vacation Rental rather than a Hotel or a Resort on your Next Vacation.


10.   Lots more freedom to do what you want when you want to.

9.     You won’t be stuck in your hotel room in the middle of the night without anything to do.

8.     Many vacation rentals come with their own pool and there are no pool hours.

7.    Vacation rentals are going to save you a ton of cash when compared to a hotel. (see infographic)

6.    You get to enjoy the vacation area more, by being part of the community of vacationers that either have second homes in the vacation destination or that live there.

5.   There’s lots of room for the whole family.

4.  You’ll have a kitchen and usually a washer and dryer.    This is a great way to save on eating out “all the time” and cleaning fees.

3.  You can walk down the hallway of your vacation rental naked and no one will say a word.

2.  It’s like being in your own vacation home.

1.  You get to relax and enjoy yourself at your own pace without room cleaning knocking on your door every few hours.

Rent directly from a vacation rental owner and save $$$.  Check out the listings on vacationdiggs and if you have any questions about the process of renting a home please let me know and I can help you.    Happy travels!

vacation rental homes versus hotel comparison infographic

Travel Ideas infographic from HomeAway

Simply Ibiza


2 minute walk from the beach and 10 minute walk from San Antonio centre, prime location, excellently priced.
SAVillaThis villa is warm and cozy located on the main road leading into San Antonio, just a short 10 minute walk from the beach.

The fantastic location has all the major attractions of San Antonio including the famous Eden & Es paradis nightclubs can be reached in a quick 15 minute walk. The islands hottest new beach club is Ocean Club Ibiza is practically on your doorstep.

For more info. on this rental visit Simply Villas

“Who’s to say what a ‘literary life’ is? As long as you are writing often, and writing well, you don’t need to be hanging-out in libraries all the time. 
Nightclubs are great literary research centers. So is Ibiza!” 
― Roman Payne

Vacation Rentals save more than Sense

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Wether going on a family vacation or a long term stay a vacation rental can save you a bunch of cash and provide amenities and an experience that you won’t find at a resort.

San Antonio, Texas – is the newest vacation rentals site on the internet though its founder Angelica Alaniz, isn’t new to promoting and renting vacation rentals to travelers looking for a different type of vacation to a traditional resort of hotel.  Alaniz was the founder of 2 of the internets first vacation rental sites, and, sites that she sold early in 2004.  Angie is back in the vacation rental listing site business again with her latest venture, With a passion for finding travelers great deals and internet promotion it’s not surprise that Alaniz is back in the vacation rental business.

I sat down with Angie a few days ago and asked to discover “why vacation rentals?”

Perhaps this is a common question though I’m curious why would anyway want to stay at a vacation rental rather than a resort?

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“There are numerous benefits of vacation rentals especially during the uncertain economic conditions that we face. Vacation rentals are great for both highly-budget conscious travelers, those on a tight budget or large groups looking to stay in a beautiful villa with incredible amenities — often at far less than the cost of renting hotel rooms.

Yes, a terrific vacation rental is going to require slightly more due diligence than staying at a well known resort, though the internet provides many ways today to ensure that you are getting exactly what the vacation rental owner says you are. With some searching and reading reviews, today’s savvy traveler can find a much better travel experience, nicer accommodations than a hotel room at a fraction of the cost. Nicer is somewhat personal taste though it’s certainly a “slower” and more “real” type of experience.

One of the major benefits of vacation rentals is you get more for your money. Vacation rentals typically provide you with far more privacy than than a single hotel room. For example, in the Caribbean or Hawaii at the same price as a two or three star hotel room, 3 couples can stay at a condo each couple will have the privacy of their own bedroom for what would typically be the cost of one hotel room. Now’s that’s tough to beat especially when you look at all the other amenities that come with vacation rentals.

Vacation rentals, like resorts, come in all shapes and size. They range from small studios in places like Paris and London, where staying at a hotel can be outrageously expensive, to villas that are suitable for royalty though when shared by a large group typically are extremely affordable especially in comparison to a hotel or resort.

Another major benefit of vacation rentals is that you can typically save even more based on longer term price breaks. Almost every vacation rental owner offers a number of price breaks that include weekly and monthly rental rates. For even longer term stays you can typically negotiate an even larger discounted rate, have the owner waive cleaning fees or include extra cleaning.

One of the other considerations for staying at a vacation rental is you get to be part of the “slow” travel movement. Instead of being rushed by the hustle and bustle typically associated with a resort, when you stay at a vacation rental you’ll typically be located in a residential resort community where you can live as the locals and long term residents do – or go into the faster paced lifestyle of the resort area. In Europe, vacation rentals are often located found away from the usual tourist spots, perfect for those trying to get off of the beaten path.

Staying at a vacation rental is also be terrific way for the budget conscious traveler to be able to stay at a better location than they could in a hotel. In places such as Cabo San Lucas or Hawaii, where there is a huge number of condos and villas, you can find great diggs right on, or near the beach, just the kind of location almost all vacationers would love and at far less than the price of a hotel room.

There are also other more obvious benefits of vacation rentals such as a full kitchen (great for saving money by eating in), often your own swimming pool or a shared one, many rooms just for you and your guests and the feeling that this is your home away from home. Typical other benefits of vacation rentals may include free equipment use, such as snorkels, boats, bicycles, surf boards and the extremely important washing machine.

Having stayed at many vacation rentals the experience is something that a traveler should discover :). It’s a wonderful way to travel and really get a feel for the place and save money while there.”

Thanks for sharing I’m definitely going to check out what you have at