Eight Rules to Get the Best Timeshare Rental Deals

Timeshares present an opportunity to realize a great vacation value.  However, if you are careless or impressionable, timeshares could cost you big bucks and lead to financial disaster.  Here are my eight rules to show you how to get the best timeshare rental deals.

Disney's Saratoga Springs Resort

Downtown Disney as viewed from Disney’s Saratoga Springs Resort

1.  NEVER, NEVER, NEVER BUY A TIMESHARE. Let me repeat that…NEVER buy a timeshare. Somewhere a scumbag timeshare salesperson is shedding a tear over that statement. Don’t feel bad for them. They have chosen a profession intent on ripping off hard working men and women who fall prey to their misleading sales pitches. If you want to accept a $150 to $300 bauble (free dinners, free tickets, discounted stays, etc.) and waste two hours of your vacation undergoing the verbal equivalent of an enema be my guest, but only if both you and your significant other are 100% committed to saying NO!!! Remember, you will have to say NO about three hundred times before the rabid dog timeshare robot will let you leave with your crappy gift. Be strong. Be firm. Walk away with your head held high (and your bank account undamaged) and a timeshare promo goody in your hand. Better yet…don’t bother going to the ridiculous timeshare presentation and head to the pool with the kids. I guaranty you a much more joyful experience.

The corollary to Rule 1 is NEVER, NEVER, NEVER BUY A TIMESHARE FROM A TIMESHARE DEVELOPER. If you absolutely love the timeshare concept and you’re pretty sure you will go every year, you can purchase a timeshare on the secondary market. I would only do so if you are buying it for a song–5% to 15% of the original purchase price. Remember, the owner you are buying from is a guy who is trying to get out from underneath the annual membership dues. Negotiate your timeshare resale purchase with that in mind.

Marriott's Grande Vista

Marriott’s Grande Vista Main Pool

2. RENT…RENT…RENT. Want to have a great timeshare experience—rent one from an existing owner. There are a number of great timeshare rental websites that can point you in the right direction.  There are also more than a few crappy timeshare rental sites. The good ones connect you directly to the timeshare owner. The bad ones try to step in-between you and the timeshare owner and add a layer of cost. Two sites stand well above the fray—eBay.com and Redweek.comeBay.com is a great resource for timeshare rentals although inexplicably their lodging searches cannot be refined by date. That’s a major flaw that an intelligent search can partially overcome (of course, it would be smarter for eBay just to fix the flaw). On the upside, eBay requires all individual travel sellers to become “eBay Travel Verified” before they can create an eBay travel listing. In order to become eBay Travel Verified the seller must prove his/her ownership of the timeshare week to eBay. Thus renting a timeshare on eBay gives you an additional level of comfort that you don’t get on most timeshare rental websites. I joined Redweek.com three years ago for free (grabbed a complimentary one year membership coupon code) and have renewed my membership twice for $14.99 a year. This will be the best money you ever spend on a timeshare. Redweek.com is well organized and acts as an intermediary between timeshare owners (who pay a fee to list the weeks they want to rent) and those interested in renting timeshares. Members can email other members directly to negotiate the terms of the timeshare rental. I also want to give a shout out to TUG2.com (which stands for Timeshare Users Group). They do a really nice job bringing together resources for people interested in the timeshare market. There is also a timeshare rental market on TUG2.com. You can also find timeshare rentals on sites like www.vrbo.com and www.airbnb.com.


Disney's Saratoga Springs Resort

Disney’s Saratoga Springs Resort

3. DO YOUR HOMEWORK.   My suggestion is to stick to the bigger timeshare developments—Marriott, Westin, Hilton and Hyatt have some outstanding properties. Check out the pictures and reviews of any timeshare you’re interested in on Tripadvisor.com before taking any action on Redweek.com or Ebay.com. Most of the smaller developments have very sporadic rental availability thus it’s harder to land a good week and harder to figure out correct pricing on the units that may be available.

Marriott's Harbour Lake Resort

Marriott’s Harbour Lake Resort Main Pool

4. NEGOTIATE. Once you decide where you’re going check out the availability for your dates on EBay.com and Redweek.com. For example, in December, 2014, I rented a one bedroom villa at Disney’s Saratoga Springs resort in Lake Buena Vista, Florida. The owner was asking $160 a night for the week of December 11-18. However, it was already December 2—time was running out for the timeshare owner. Accordingly, I sent him an email offering a $100 a night and he accepted a day later (later he offered another $100 off the original weekly price because he had screwed up the dates in his Redweek advertisement). Keep in mind that there were a number of other one and two bedroom villas available for that week at the Saratoga Springs on a number of popular timeshare rental websites. Some of those people held out for their listed rental price and failed to rent their units. Resultantly, those poor souls had to shell out the approximately $750 to $1000 annual fee to Disney for nothing.

Disney's Saratoga Springs Resort

High Rock Springs at Disney’s Saratoga Springs Resort

5. TIMESHARES ARE A “USE IT PROPOSITION OR LOSE IT”. Generally, if the owner can’t rent or use his/her timeshare by the specified date they are out of luck. They lose their timeshare privileges for that year. Those owners get zip, nada, bupkis, diddly for their timeshare investment. Sometimes they can redeposit the weeks through RCI (a large timeshare clearing house), but RCI charges some hefty fees for the privilege. Accordingly, for the most part the timeshare owner needs to part with these weeks prior to the specified timeshare date. Advantage timeshare renter. Feel free to negotiate with that in mind.

Marriott's Cypress Harbour Resort

Marriott’s Cypress Harbour Resort

6. DON’T BE UNREALISTIC. Don’t get crazy and offer someone $10 for a week that should be worth $1,000. Be tough, but maintain a sense of fairness when you deal with timeshare owners on the web. You can generally find out how much the timeshare owner pays in annual fees by checking the “for sale” section on Redweek.com (or on any other timeshare resale website) and then checking the annual “maintenance fees” section. These fees can vary substantially from owner to owner depending on (a) when they purchased their timeshare, (b) the size of the unit (studio, one bedroom, etc.), and (c) whether their timeshare is for high or low season. Doing this research gives you a very good idea of how much the guy your negotiating will be out if he can’t rent his unit. Then check out how many units are up for rent for week you intend to rent. Those two juicy pieces of information are all you need to develop a smart negotiating strategy. Just FYI there will always be a certain group of timeshare owners who place ads hoping that someone will come along and pay two or three times the going rate for their generic timeshare. Ignore those ads. They are a complete waste of time for everybody. Happy negotiating!!!

Disney's Old Key West Resort

Disney’s Old Key West Resort

7. DO I NEED A TIMESHARE RENTAL CONTRACT? The not so simple answer is yes and no. Is it better to execute a timeshare rental agreement—yes. Is it absolutely, positively a precondition to renting a timeshare—no. With apologies to my brilliant law school Contracts professor Richard Danzig, the transaction amounts involved in timeshare rental agreements are small (and the complexities are few) making the execution of a formal contract a matter of personal choice.   That said—it is always better to have one in place as the contract will clearly lay out each parties’ responsibilities and obligations. Tug2.com has a sample timeshare rental contract should you elect to go in that direction.


Disney's Saratoga Springs Resort

Bridge at Disney’s Saragtoga Springs Resort

8.  PAYMENT FOR YOUR TIMESHARE RENTAL.   Once you have completed negotiations you have to arrange a safe way to pay the owner for his/her week. Obviously, cash is out of the question. You could send a check or money order—again not ideal and not recommended. PayPal is a good bet for these types of transactions.   My suggestion is to send 25% to 33% of the rental amount via PayPal after you finish negotiations with the timeshare owner. Once the timeshare owner places the reservation in your name and emails you a confirmation (which you should independently verify directly with the resort or timeshare company), you can pay the balance (preferably as close to the timeshare rental date as possible). Keep in mind that even this isn’t ideal. PayPal has a wonderful suite of fraud protections but this class of transaction is not covered. You are still at risk of an unscrupulous owner changing the reservation prior to your arrival. I’ve rented through Redweek numerous times and have never had an issue. Additionally, most timeshare companies charge owners a fee to change the name on the reservation. Accordingly, fraudsters will generally not go so far as to actually make the reservation in your name. Both eBay.com and Redweek.com work hard to weed out any bad apples…but anything is possible.  eBay does offer a distinct advantage with its eBay Travel Verified program. However, the only foolproof way to absolutely guaranty against loss is to use an escrow service (usually a title company). They hold your money in escrow and release it under the terms of an Escrow Agreement between you and the timeshare owner. The problem is they charge very high fees for these services. For example, I would have shelled out another $100 for escrow protection for my Saratoga Springs rental. I think you get a good sense about whether or not the timeshare owner you’re working with is legit through the email exchange leading up to the transaction. The choice is yours.

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  1. Pingback: Top 10 Cancun Hotel Deals From $50 a Night! - Traveldealalert

  2. Very good article, just wished i had read this soner. I am one of those poor souls that dreamed about traveling n creating life time memories w my family n fell for the high pressure sales pitch n lies. It’s true, timeshare sales people are ruthless n they lie. Anyway I’ve ended up w two timeshares n have spent a lot of money on them so now I’m just trying to minimize my losses n trying to rent out my weeks on redweek n tug2. I’d be happy if i can just get some $ back, forget about making any, just recoup some $ by letting someone else use it.

    • Thanks for your input. Good luck renting your timeshares. Both Redweek and Tug2 are excellent resources for both timeshare owners and renters.

    • Thanks so much. I really appreciated your feedback. I have not contributed in a while but i am planning to come back soon.