BeachSide vacation rentals

We found 34 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Frequently asked questions

What are the top vacation rentals in or near BeachSide?

Whether you're looking for an intimate retreat for you and your love or someplace roomy to fit family and friends, you'll find some top vacation rentals in and around BeachSide. Here are a couple we think you'll like:

  • Make use of amenities including a kitchen island and a boat at "Key West Oasis, Seperate Cottage". Situated around 2 miles from BeachSide, this unique property has 2 bedrooms and good guest reviews.
  • Another excellent choice is "Cloud 9 ~ It's Heaven On Earth In This 3b", which is around 3 miles from BeachSide. Offering 3 bedrooms, a microwave oven and an ice maker, it has everything you need to make your stay comfortable.

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

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

Your working week will be easier to face if you've got something awesome planned for the weekend. Give yourself something fun to look forward to by arranging a stay at one of these top weekend getaways in or near BeachSide:

  • Book a few nights at "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach", around 1 mile to the east of BeachSide, and you've got yourself the ultimate weekend break. You'll have natural attractions like Sandspur Beach and Boca Chica Beach nearby and conveniences like a stovetop and a garage to make the most of.
  • Another appealing option is "Starfish - Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St", around 4 miles west of BeachSide. When you're not kicking back in your rental making the most of off-street parking options and spa and beauty services, check out some of the area's highlights like Upper Sugarloaf Sound and Blue Hole.

Can I find studio apartments for rent in and around BeachSide?

Appreciate the culture and lifestyle of BeachSide from the comfort and privacy of your own studio apartment. Whether you're planning to chill on your own or have fun with a few friends, we'll help you find the perfect studio apartment in or near BeachSide:

  • Make "Condo In Old Town Key West's Truman Annex" your temporary home. This great vacation rental features amenities including nearby birdwatching activities and air conditioning.
  • Alternatively, spend your escape at "Your Condo By The Beach With Ocean View", which offers conveniences such as a balcony and an oven.

There are loads of attractions around BeachSide to put on your must-do list. Satisfy your inner culture lover and visit Key West Museum of Art and History and Key West Art and Historical Society.

Can I find short term rentals in or near BeachSide?

Now and then, you've just got to take a well-earned breather, even if it's only for a few days or so. Enjoy the perfect combination of relaxing and exploring at one of these short-term rentals in or around BeachSide:

  • If you're eager to be close to the action, "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach" has your name on it. It's within reach of the heart of BeachSide and a convenient base to discover sights like Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens.
  • Sleep, relax and explore from "Villa Josine ~ 4 B/4. 5 Ba Large Designer Home With Pool In A Great Location", another excellent option. Smathers Beach and Southernmost Point should be on your must-do list when you're ready to sightsee.

What are the best romantic weekend getaways in or near BeachSide?

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a fantastic way to say "I love you." Whisk your honey away for a couple of leisurely days at one of these popular escapes in or near BeachSide:

  • Slip away on Friday for a couple of passionate nights at "Key West Oasis, Seperate Cottage". Located approximately 2 miles from BeachSide, this property comes with lots of nice touches, like beauty services and a dining table.
  • Another place where you can enjoy a few idyllic days together is "Cloud 9 ~ It's Heaven On Earth In This 3b". Around 3 miles from BeachSide, a swimming pool and a dining table add to the atmosphere here.

Are there mansions for rent in or near BeachSide?

If you're searching for somewhere to reconnect with loved ones this vacation, why not go all out? These mansions for rent in or around BeachSide will easily fit your entire crew while doing it in style:

  • Character, style and charm — "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" has it all in abundance. Around 4 miles west of BeachSide and offering a swimming pool and golf, this place is hard to beat.
  • With golf, concierge services and a host of other top-rated amenities, "Captiva" ~ , Historic Mansion Suite With Community Pool" will dazzle you and your guests. This opulent home is roughly 3 miles to the southwest of BeachSide.

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

Sneak a peek at these large group vacation rentals in or near BeachSide and don't worry about leaving anyone off your invite list:

  • A wealth of amenities including a water view and a beach view make "New Photos: Drive To Your Getaway" a favorite. This property has 5 bedrooms and sleeps up to 12 people. From the center of BeachSide, it's around 3 miles away to the southwest.
  • Invite as many as 14 of your dearest friends to "William Skelton Home - Heart Of Key West" and fill its spaces with laughter and love. This popular option has 6 bedrooms and is around 3 miles to the west of central BeachSide. It's packed with features to keep a large group comfortable and content, such as a kitchen and a swimming pool.

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

A pool is often a must-have amenity for any memorable vacation. Enjoy hours of entertainment splashing around or simply kicking back by the water at one of these rejuvenating escapes in or near BeachSide:

  • Make pool day every day at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". A swimming pool and a stair gate are a few of the other amenities that help make this place a standout.
  • Alternatively, make a booking at "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" and spend your break poolside. A garden and nearby ecotour services are other things your gang will like about this rental.

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

Every catch-up with the family should be memorable. Whether you're planning some time off with the kids or a long-overdue family reunion, these large family vacation rentals in or near BeachSide offer a comfy home away from home with plenty of space for everyone:

  • Get your nearest and dearest under the same roof at "Cloud 9 ~ It's Heaven On Earth In This 3b", which has 3 bedrooms that sleep up to 7 guests. This getaway is around 3 miles to the west of BeachSide and comes with amenities such as towels and a swimming pool.
  • Another top choice is "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach". This property is 1 mile east of BeachSide and comes with a fridge, a swimming pool and more. With 3 bedrooms accommodating up to 8 people, don't worry about leaving anyone off your guest list.

When you want to explore your surroundings, there are plenty of family-friendly attractions in the area to keep everyone happy. Duval Street, Key West Aquarium and Key West Wildlife Center should be at the top of your itinerary.

Can I find family cabin rentals in or near BeachSide?

Nothing is more important than family, which is why we'll help you find a place where you can truly connect. Stay in one of these family cabin rentals in or near BeachSide and make wonderful new memories with the people you love the most:

  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - This sought-after escape offers cable/satellite TV services and a fridge and is located approximately 3 miles to the southwest of central BeachSide.
  • "Cabin - Hidden Treasure - 2 Bedroom 2 Bath With Shared Pool" - Another terrific option, this cabin comes with a dishwasher, a microwave oven and more. You'll find it around 3 miles to the southwest of BeachSide.

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

Are there one-bedroom vacation rentals in or near BeachSide?

Often situated in prime positions due to their smaller size, a one-bedroom rental is a great choice for one or two travelers. Check out our range in or near BeachSide:

  • Check into "Your Condo By The Beach With Ocean View" for a few nights. This one-bedroom vacation property comes with a swimming pool and an ocean view and is close to the heart of town.
  • "Beach House With Ocean View - No Contact Check" is another comfortable one-bedroom escape also close to the center. When you're not out discovering the area, enjoy a kitchen and a swimming pool.

Can I find two-bedroom vacation rentals in or near BeachSide?

Yes, you can. From funky apartments to comfy cabin retreats, Vrbo has a range of vacation rentals. Smaller families will like these two-bedroom properties in or near BeachSide:

  • Leading our list is "Key West Oasis, Seperate Cottage". This two-bedroom stay provides handy amenities like a swimming pool and a kitchen. Explore BeachSide's excellent attractions from this homely pad.
  • "Natures Edge @ The Beach Ocean Condo" is another lovely two-bedroom place. It comes with a swimming pool, a sauna and much more.