Discover a selection of 491 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 $131 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.

Things to do

Activities and attractions in and around Stock Island

Are you hoping to discover attractions to visit in the city? Venture out of your cozy vacation rental and experience everything that makes Stock Island a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Key West Golf Club (0.4 mi / 0.6 km)
  • The Kite House (3.8 mi / 6.1 km)
  • MLK Community Pool & Community Center (4.1 mi / 6.6 km)

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.

What are the top vacation rentals in or near Stock Island?

The heart wants what the heart wants, and right now it wants to take a vacation. It's time to pack your suitcase and retreat to one of these top vacation rentals in or near Stock Island:

  • Make use of handy amenities like air conditioning and WiFi at "Key West Oasis, Seperate Cottage". Situated around 4 miles from Stock Island, this property has 2 bedrooms and good guest reviews.
  • Alternatively, make yourself comfortable at "Cloud 9 ~ It's Heaven On Earth In This 3b". Located around 4 miles from the heart of Stock Island, it has 3 bedrooms and comes with shopping and nearby ecotour services.

For even more great options, use the search bar at the top of the page to find the perfect Stock Island vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Stock Island?

There's nothing like a quick break to reset your batteries. If you're ready to switch off and relax, these top-rated weekend getaways in and near Stock Island make a terrific base for a mini break:

  • If spending time in the outdoors is a top priority for you, consider "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". Around 0.1 miles northeast of Stock Island, it's close to Cook Island and Fort Zachary Taylor Historic State Park. Top amenities at this retreat include a beach and an iron and ironing board.
  • "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St" is also perfect for a whirlwind getaway. About 4 miles to the west of Stock Island, this vacation rental comes with amenities such as a nearby bay and a microwave oven. Simonton Beach and Key West National Wildlife Refuge should be on your sightseeing list if you stay here.

Can I find studio apartments for rent in and around Stock Island?

Generally small, easy on the pocketbook and conveniently located, it's not hard to fall for the charms of a studio apartment. Get comfy in one of these options and get to know Stock Island up close:

  • Throw your suitcase down at "Condo In Old Town Key West's Truman Annex". Amenities including a TV and nearby whale-watching activities help make guests feel right at home here.
  • Alternatively, organize a stay at "Your Condo By The Beach With Ocean View", which comes with conveniences including an outdoor pool and towels.

With the cash you save on your studio apartment, you'll be able to explore more of Stock Island. Cultural sights like San Carlos Institute - Casa Cuba and Red Barn Theater will help you better understand the personality of this destination.

Can I find short term rentals in or near Stock Island?

Just because you only have two or three days off work doesn't mean you have to spend it in a soulless hotel room. Get away but still have the home comforts you love at one of these short-term rentals in or around Stock Island:

  • "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" is close to the center of Stock Island, which means there are lots of things to keep you entertained. Explore leading attractions like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens when you're not relaxing in your cozy rental.
  • Sleep, eat and explore from "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location", another enticing option. Smathers Beach and Southernmost Point should be on your to-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Stock Island?

Nothing says "I love you" like a romantic weekend trip. If you're eager to spend a couple of relaxing nights away with your partner, we've got some romantic getaways in and around Stock Island that will set your hearts aflutter:

  • Around 4 miles from Stock Island, "Key West Oasis, Seperate Cottage" is the perfect place for adoring couples. Beauty services and a dining table are among the many amenities you'll find here.
  • "Cloud 9 ~ It's Heaven On Earth In This 3b" is another wonderful option that'll woo you. It's about 4 miles from Stock Island and has a swimming pool and a dining table.

Are there mansions for rent in or near Stock Island?

We've got some incredible mansions for rent in and around Stock Island. If you're looking for somewhere with lots of space as well as a serious dose of wow factor, these stunners will not disappoint:

  • Located about 4 miles to the west of Stock Island, "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" is the perfect place to relax and unwind in luxury. Amenities on offer here include a swimming pool and beauty services.
  • Alternatively, catapult your vacation to a new level and settle into "Captiva" ~ , Azul Historic Mansion Suite With Community Pool". It's approximately 4 miles to the west of Stock Island and offers amenities like a swimming pool, concierge services and more.

What are the best large group vacation rentals in or near Stock Island?

Vacation with others and boost your odds of having fun. Whether you're organizing an action-packed escape with pals or a big family gathering, there's no shortage of large group vacation rentals in and near Stock Island:

  • A range of amenities including a water view and a swimming pool make "New Photos: Drive To Your Getaway" a favorite. This expansive retreat has 5 bedrooms and accommodates up to 12 guests. From central Stock Island, it's around 4 miles away to the southwest.
  • "William Skelton Home - Heart Of Key West" is another fantastic option. It's around 4 miles to the west of Stock Island, has 6 bedrooms and welcomes up to 14 guests. A swimming pool and a garden are just a couple of things that'll help make your visit more comfortable.

What are the best houses for rent with a pool in or near Stock Island?

From lively games of sharks and minnows to leisurely dips, a pool promises plenty of fun for both adults and kids. Score some brownie points with the family by booking a house with a place to swim in or near Stock Island:

  • Pack your swimsuit and enjoy a fun stay with your group at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". Other amenities here include a microwave oven and a stair gate.
  • "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" is another highly rated option. After you've enjoyed a dip with the kiddos, make use of on-site watersports and books.

What are the best large family vacation rentals in or near Stock Island?

Whether your idea of the perfect escape is out in the countryside or by the ocean, you'll have a lot more fun if you share it with those closest to you. Look up these large family vacation rentals in or near Stock Island and bring the whole gang along:

  • About 4 miles to the west of Stock Island, "Cloud 9 ~ It's Heaven On Earth In This 3b" has 3 bedrooms and can sleep up to 7 guests. It comes with a range of amenities, including towels and a nearby coin laundry.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" is another popular option. It's around 0.1 miles to the northeast of Stock Island, has 3 bedrooms and can accommodate up to 8 guests. Handy amenities here include a garden and a porch.

If you're in the mood to sightsee, there are lots of family-friendly attractions nearby to put on your wish list. Duval Street, Key West Aquarium and Key West Wildlife Center are great places to start.

Can I find family cabin rentals in or near Stock Island?

Cozy up with the kiddos in a family cabin rental in or near Stock Island and make some incredible new memories together. Here's just a taste of what we've got:

  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - Approximately 4 miles west of central Stock Island, this family-friendly escape offers amenities like a fridge and coffee and tea making facilities.
  • "Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool" - Gather up the troops and spend a few nights at this welcoming property, which is around 4 miles to the west of Stock Island. You'll have access to a swimming pool, a fridge and a good deal more.

For more options, use the search bar at the top of the page and adjust the filters to find the Stock Island vacation rental that's perfect for your needs.