Discover a selection of 425 vacation rentals in Stock Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $135 per night, and houses and boats are popular options for a stay in Stock Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Stock Island
Destination guide

Key decisions in Stock Island

On a low-lying island in the Atlantic Ocean, Stock Island is a residential community known for its laid-back lifestyle, waterfront marinas, and easy access to some of the best beaches in the Florida Keys. Just east of Key West, Stock Island is a major destination for watersports, and you'll find everything from jetskiing and boat charters to snorkeling, sunbathing, and fishing. And with a Stock Island vacation rental, you'll be close to local landmarks like the Key West Tropical Forest & Botanical Garden, the Key West Golf Club, and the Ernest Hemingway Home and Museum.


Stock Island – water you waiting for?

It may be small, but Stock Island's got plenty to do. Boating is a popular pastime, and you'll find a number of outfitters offering fishing and sightseeing charters, as well as dolphin- and shark-watching tours. Watersports are also a big draw, and you can enjoy everything from snorkeling and scuba diving to jetskiing, parasailing, and windsurfing. And if you'd rather just lie on the beach and catch some rays, well, that's fine too – the nearby Smathers Beach boasts a half mile of sandy coastline along the southern coast of Key West.


Set fire to the rain on Stock Island

Like much of the Florida Keys, Stock Island has a tropical wet-and-dry climate, which means hot, wet summers and warm, dry winters. Rainy summer storms are common, and average highs hover near 90ºF from June through September. Winter is drier, with highs around 75ºF in December, January, and February. Thanks to the mild, sunny temps between November and April, Stock Island is a popular destination for visitors escaping harsher weather farther north. If you don't mind packing an umbrella, you can score a sweet deal on a Stock Island vacation rental during the warmer, wetter summer months.

Natural features

Stock Island – it's all within your beach

Set on a small, low-lying island in the Florida Keys, Stock Island is basically the platonic ideal of island living. While the island is relatively residential, there are still large swaths of undeveloped space, mostly on the northern side of the island. Boasting a wide array of native flora, The Key West Tropical Forest & Botanical Garden offers a glimpse of the island's former, untamed splendor. At the nearby Smathers Beach, on Key West, you'll find half a mile of sandy shoreline, and it's a popular place to spot dolphins and the area's bounty of brightly colored fish.

How many vacation rentals are available around Stock Island?

Our 2022 property listings offer a large selection of 425 vacation rentals around Stock Island. From 137 house rentals to 32 boat rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Stock Island?

Yes, of course. Vrbo has 137 Houses in Stock Island. Our other popular types of vacation rentals in Stock Island include:

  • Boats: 32 rentals available
  • Condos/Apartments: 106 rentals available
  • Townhouses: 42 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Houseboats and more.

Can I find a vacation rental with pool in Stock Island?

Yes, you can select your preferred vacation rental with pool among our 333 vacation rentals with pool available in Stock Island. Please use our search bar to access the selection of vacation rentals available.