You’ve always known and now its scientifically proven, vacations are essential to living happy healthy complete lives.  Here’s how to travel farther for less and do it without causing financial stress. 


I’ve always preferred vacation homes to hotels.  Not only do vacation rentals deliver more charm and intimacy than a hotel, but they are also “on average” much cheaper. How do they do that?  Vacation rentals have lower overhead and the owner retains use of the residence when you aren’t there.  It’s a cost advantage hotels cant touch.  

Using the Siesta Key market during December 10th to the 17th as a test case.  Our 1 bedroom vacation rental costs $650/week while suites at the nearby Tropical Breeze Resorts hotel are slightly over $850/week.  Not a huge difference, but its enough to rent scooters at Robin Hood Rentals during the stay, get a couples massage at Hands of Light with cocktails after, or pay the tab at breakfast the entire week.  As the size of your group grows, so does the savings.  Our weekly rate for a 3-bedroom house with an occupancy of 10 is just $1400.  That’s just $470 per room per week and, if you just partially fill it with 8 people, the rate becomes just $175 per week per person or a savings of over 50%.  So that means you can take two vacations in a 3-bedroom vacation rental for the price of just one trip when booking three hotel rooms.

Note – You may have to give up a pool to do this, but Siesta Key is the best beach in the country.  Put a pool on the “must have” list when you visit Las Vegas, but when visiting Siesta Key skip it because you might not miss it.


Siesta Keys beaches are free, but Disney is now $100 per day for guests over the age of 10.  If you want mouse ears with embroidery Disney is an additional $30 per person. The theme parks always seem like a good idea when you are at home on the couch watching a commercial for the Magic Kingdom, but I’ve never heard anyone sitting on the beach say “I wish I was waiting in line for rides at Disney!” Skip the theme park and save $800 per day or $5600 per week for a family of 8. 


Host pre-bar and post-bar get-togethers onsite.  Going out is great, and you will, but the main purpose of a trip is to beach, bond, and make memories that last a lifetime and that doesn’t have to be expensive.  Pre and post-party at your rental to save on drinks.

Hosting a cocktail hour(s) at your vacation rental means having a private bar where you control the door, the volume of the music, and the TV channel.  A liter of Svedka, a great discount vodka, is just $14 and at 1.5ozs a cocktail you can make 22 drinks.  That is about a one dollar per drink with mixers and that’s seven dollars cheaper   (when adding tip) than cocktails at the Siesta Key Oyster Bar.  You also get a real glass and don’t have to wait in line for it.  Doing the math, if my wife drinks 5 drinks and I drink 12 drinks (don’t judge me, that’s “all day”) the savings is over a $100 for us. 

When travelling with groups take turns hosting.  This will inject a healthy dose of rivalry to help keep the signature drink fresh and adventurous.  I like a Madras, that’s Svedka, OJ, cranberry and lime.  If you want, dress your drinks up with swizzle sticks and designate the member of your group with the most tattoos to bartend (usually me).  Drinking on a patio on Siesta Key is amazing and alcohol is even legal on beaches in Sarasota, but don’t take glass there.  The bars on Siesta are also amazing, but it’s tough to compete with alfresco cocktails.  

To keep the cleanup easy, have plenty of garbage bags in-site of guests, centralize the party in one spot, and use a Sharpie to label guest cups. If putting names on cups feels like a downer for you, use a “call-sign” in lieu of a name.  It’s also fine to ask your guests for help cleaning.  If I kick off the cleaning myself, brew some coffee and put on an upbeat playlist, my guests usually fall in line.  

NOTE – Most vacation rentals have “shared” outdoor areas so check your vacation rental provider for any curfews.  My communal area curfews close at 10pm. When you just have to get a change of scenery, consider a happy hour at the Summer House, SKOB or the Hub and drink two for one. 


The markup at restaurants in vacation markets after tax and tip is near 250%. You can cook at home, save a lot of money, and still keep the work at a minimum.  The Summer House Restaurant is amazing, but save it for a night when you are really dying for something with a potato-lemongrass crust! 

For lunches and dinners grill your own fresh meats and re-serve previously produced sides. Don’t buy a lot of ingredients you’ll just throw away when you leave, just keep the meat dish simple.  You can’t go wrong grilling with olive oil, lemon, salt and pepper.  It simplifies prep and cleanup and, at Gertrude Rentals, we’ll clean the grill for you when you leave.  For your sides, pick up pans of restaurant sides and spice it up with one homemade specialty side from each member of your party.  I like a tomato and strawberry salad with a lot of basil and balsamic, its great cold or room temp. 

Barbecue restaurants and fish markets are a great source for fresh meats and sides by the pound.  You’ll find better prices off the island.  I like Walt’s Fish Market, Pride of the South Barbeque, and Publix in Paradise Plaza, each is just about 4 miles from the Siesta Key Village.  A 12ozs of rib eye steak at Publix is $8 and 8ozs of Mahi-mahi is just $8 at Walt’s Fish Market, but entrees at the Summer House range from $30 to $40.    

If you are feeling ambitious take the meal down to the beach or just wander your neighborhood with a plate.  To make hosting easier – keep garbage cans and bags available and in-sight, avoiding serving messy foods, always do it buffet style, invest in sharpie and label drink cups, then centralize the party and eat outside.  Share the cleanup by alternating family members.  

NOTE – Many rentals have smaller fridges so take a look at the size of your fridge before shopping.  When you just have to get a change of scenery, consider hitting an early bird special.  Turtles-on-the-Bay hosts an early bird from 3PM to 6PM with two for one drinks.  You can fill up and still get home for Sunset and maybe even time for a pre-sunset nap.


Find a vacation rental or hotel close to your main attractions and skip the rental car.  Because of zoning limitations, vacation rentals frequently have access to neighborhoods hotels don’t. 

Any Siesta Key Village or Crescent Beach property is going to be walking distance to plenty of bars and restaurants.  Some parts of Siesta are a little further from these attractions, but the island does have free taxis and a free trolley running along the beach. 

Rental cars might make sense for longer stays or locations where attractions are spread out.  In this instance, save by reserving your car when you book your flight, but watching for a cheaper deals prior to pickup.  Keep in mind rates are constantly changing and the rental-car business model you’re reservation isn’t a financial commitment.  You can search manually or set up alerts at sites like Auto-slash or Expedia.  Also try entrusting a member of your party with “free hands” to search for a lower rate while you are walking through the airport or even waiting in line for your car.  Depending on the season, that could be a savings of $100 or more per day.  

NOTE – Because of parking constraints and traffic I don’t recommend staying anywhere on Siesta where you are too far away from the beach to walk there.  Honestly, don’t do it.  


Travelers really hold all the cards when it comes to airline tickets.  Flight aggregator sites are fantastic tools and, if you are willing to invest more than 3 minutes in your search, you can really leverage them to game the airline fares.  

Adjust your travel dates a little and you might save a lot.  There is no cheap day of the week to travel, that’s a myth.  Avoiding weekends and holidays will save you a little, but keeping your dates flexible can save you a lot more.  In Orbitz for example you can complete your search then select “show flexible dates” and see the very lowest departure and return fares for every day in a two week period.  When travelling over a school holiday, consider missing one day of classes.  This may be an uncommon strategy, but as a father of 5 and former student I strongly believe the Monday or Tuesday immediately following a holiday weekend isn’t a very big day for academic growth and can tell you only one of my five kids would actually complain about missing a day of school.  

If the date change saves you $1000 (maybe much more) for the college fund and the kids do schoolwork on the flight home then it’s such a no brainer, even my 1st grader can do that math.  Searching December 24th to January 1st from Newark to Tampa I see if I move our departure date up to the 23rd I can immediately drop my fare from $509 to just $342, a savings of $167 a ticket.  That’s enough to cover the cost of an additional day in paradise. 

Using lesser-known airports for departure or arrival is another way to save a bundle.  New York City to Sarasota is my most direct route for Siesta Key, but its pricey.  I check all Tri-state airports for my departure and all over Southeast Florida for the arrival.  The best airports to fly into for Siesta Key are – Sarasota International “SRQ” beautiful and just 10 miles away, Tampa “TPA” 60 miles away, Fort Myers “RSW” 80 miles away, and Punta Gorda (PGD) and St. Petersburg (PIE) each about 60 miles away.  Orlando is always an option “MCO” and is 140 miles away, but if you have young kids, first ask yourself if you can fly into MCO without stopping in Disney.  You should also look at Miami, Ft Lauderdale and Palm Beach airports.  These will add two hours of driving time to the trip, but if flying into the east coast saves $500 your kids have iPad’s and you’d be getting paid $250 and hour to be their Uber driver so who wouldn’t take that job?

Finally, cut out the middleman.  What you might not know is aggregators like Orbitz offer ticket prices at a price markup and sometimes an additional commission. When you find a ticket that works for you on an aggregator, check the airline to make sure they don’t offer an even cheaper fare.  Booking direct through the airline will also “definitely” simplify communication and make it easier to deal with changes if an emergency comes up. 


As an owner of 16 properties, I love flexible, open-minded travellers.  I gladly give huge discounts for guests who are – 1) looking for last minute bookings, 2) willing to split a trip over two legs, or 3) who are willing to push the occupancy limit when travelling with kids. 

Travel last minute and, subject to availability, save a ton.  I discount last minute bookings at around 60% and many other owners will too.  If I have space, the guest sounds nice, and I’m not worried they will throw a frat party at the house, I’m happy to offer even my luxury properties at as much as a 60% discount.  How can you do it Dan?!  First of all, the value of the unit depreciates 100% the day after it doesn’t get booked and secondly I love repeat guests and you could be someone I want to do more business with in the future.  NOTE – “last minute booking” might mean 14 days in advance in an off-peak month, or just 5 days in advance for a big holiday weekend. 

With hard to find dates consider splitting the stay across two locations. Agents and owners with multiple properties in the same or nearby markets might be able to address your otherwise unavailable date request with a Saint Tropez /Canne-like itinerary.  When I can address a seven night stay by putting a group in one unit for three nights then moving them to another for the last four nights, often in the same neighborhood, I’ll do it and give gladly return free upgrade or a nice discount.

When it comes to the occupancy limits kids don’t always equal one person.  If you are a family of two adults and three kids and cant quite afford a two or three bedroom rental, I’m usually willing to let you squeeze into a one bedroom with a sleeper sofa.  Not everyone has the budget for a vacation but everyone needs one.

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