For a couple looking for an apartment in a European city
Best Value: A one-bedroom apartment in Barcelona with a private terrace, located just a 10-minute walk from Las Ramblas; regularly rents for $139 a night but was available at the last minute for $120 (vrbo.com).
Least Hassle: Interhome has nearly 200 rentals in Paris, such as this one-bedroom in eclectic Belleville. It's near cafés and grocers, with a Métro stop three minutes away. Rates start at $692 per week (interhomeusa.com).
Worthy Splurge: In Venice, Rental in Italy offers the Apartment Formosa, with French windows and marble floors in a 14th-century palace a few minutes from Piazza San Marco. A week's stay starts at $1,200 (rentalinitaly.com).
For a family of five looking for R&R in the Caribbean
Best Value: You can rent St. Lucia's Villa Frangipani—a three-bedroom home with ocean views and a 50-foot veranda, one mile from both beach and town in the hills of Castries—for $1,046 a week (homeaway.com).
Least Hassle: On the U.S. Virgin Island of St. John, a three-bedroom cottage called Blue Heaven Rendezvous has a hot tub with views of the Caribbean and nearby St. Croix. Weekly rates for up to six start at $2,050 (perfectplaces.com).
Worthy Splurge: Almond Hill, a three-bedroom villa with a pool in a 500-acre coconut grove near Montego Bay, Jamaica, comes with a full staff (including a butler and a gardener) and starts at $271 a night (villasofdistinction.com).
For a big group looking for a beach house in the U.S.
Best Value: In North Carolina's Outer Banks, you'll find homes perfect for groups—like eight-bedroom Here Comes the Sun, in Kill Devil Hills. It goes for as little as $1,520 a week in May, $2,920 in August (sunrealtync.com).
Least Hassle: The 2,400-acre Sandestin resort on the Florida Panhandle has 1,500 condos, town houses, and houses, so your group can hang together but still have privacy. Three-bedroom villas start at $259 a night (sandestin.com).
Worthy Splurge: Even lush, unspoiled Kauai is within reach: A five-bedroom villa in Princeville, on the north shore—a three-minute walk to a private white-sand beach and waterfall—starts at $2,500 a week (vacationrentals.com).