Discover a selection of 88 vacation rentals in Toll Gate Shores, Islamorada 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 $167 per night, and houses and condos are popular options for a stay in Toll Gate Shores. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Toll Gate Shores
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

What are the top vacation rentals in or near Toll Gate Shores?

Whatever your getaway needs, you'll find a rental in or around Toll Gate Shores that suits your style. Here are some of our favorites:

  • Around 11 miles from the center of Toll Gate Shores, it's hard to beat "Ocean View Anglers Reef - Pool". It has 2 bedrooms and handy features including a nearby beach and an oven.
  • "Aquamarine Oceanviewjuly 30" also promises a memorable escape, offering 2 bedrooms, beach towels, a toaster and more. It's around 1 mile from Toll Gate Shores.

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

What are the top-rated vacation rentals for weekend getaways in or near Toll Gate Shores?

Your Monday to Friday will be much easier to face if you've got something exciting planned for the weekend. Give yourself something to look forward to by arranging a stay at one of these top weekend getaways in or near Toll Gate Shores:

  • If spending time in the outdoors is a non-negotiable for you, book a few nights at "Luxurious Home At Beautiful Anglers Reef With Boat Slip Available". Around 11 miles northeast of Toll Gate Shores, it's near Gumbo Limbo Trail and Everglades National Park. Amenities at this retreat include cable/satellite TV services and a hair dryer.
  • "Renovated - Boat Slip, Pool, Beach" is also perfect for a whirlwind vacation. Located approximately 11 miles to the northeast of Toll Gate Shores, this vacation rental comes with amenities such as a barbecue grill and beach towels. Crawl Key and Snake Bight should be on your itinerary if you stay here.

Can I find studio apartments for rent in and around Toll Gate Shores?

You sure can. If you're hunting down a small but stylish stay, you can't go wrong with a studio apartment. These compact properties exude charm and are often conveniently found in the middle of town. We suggest the following options in or near Toll Gate Shores:

  • Get away on your own or take a few pals to "Smart Room In Beautiful Florida Keys Home". You'll have plenty of amenities at your disposal, including free WiFi and a hair dryer.
  • Another great property is "Cozy Caribbean - Style Home With Outdoor Veranda". Don't be fooled by its compact size — this comfortable apartment is packed with convenient amenities like a washing machine, air conditioning and lots more.

Can I find short term rentals in or near Toll Gate Shores?

Now and then, you just need to escape from it all, even if it's only for a few days. Enjoy the perfect combination of relaxation and adventure at one of these short-term rentals in or around Toll Gate Shores:

  • "Welcome To Paradise "sandbar Bungalow Villa" @ Anglers Reef" is close to the center of Toll Gate Shores, which means you'll have loads of things to do and see. Tick off well-known attractions like Theater of the Sea and Bud n' Mary's Dive Center when you're not enjoying your cozy pad.
  • Sleep, eat and explore from "Off The Beaten Path In One Of Islamorada’s Hidden Gem Of A Community", another excellent option. Founders Park and Islamorada County Park should be on your to-do list when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Toll Gate Shores?

Whether spent in a cabin, a cottage or a houseboat, a romantic weekend getaway is a wonderful way to add some zing to your relationship. Whisk your sweetie away for a couple of days at one of these appealing escapes in or near Toll Gate Shores:

  • Located around 11 miles from Toll Gate Shores, "Ocean View Anglers Reef - Pool" is an ideal place for doting couples. Beauty services and a music library are some of the many amenities you'll find here.
  • "Aquamarine Oceanviewjuly 30" is another popular option that'll impress. It's approximately 1 mile from Toll Gate Shores and comes with a resort and beauty services.

What are the best large group vacation rentals in or near Toll Gate Shores?

Big groups mean a whole lot of fun. They also mean finding a place that'll comfortably fit your whole gang. Browse our large group vacation rentals in or around Toll Gate Shores and spend time with your favorite people under the one roof:

  • You'll have plenty of space to spread out at "Come Experience The Florida Keys At Sunset Cove". Around 0.1 miles southwest of Toll Gate Shores, this generous retreat has 4 bedrooms accommodating up to 12 guests. Quality amenities include a nearby waterfront and a balcony.
  • Nothing takes priority over spending precious time with loved ones, and "Waterfront Beautifully Renovated 6 Bedrooms 4 Bath" is the ideal place to do that. Located around 0.1 miles to the east of Toll Gate Shores, as many as 12 people can stay in this vacation rental which has 6 bedrooms. A garden and a swimming pool are among the numerous amenities you'll have at hand.

What are the best houses for rent with a pool in or near Toll Gate Shores?

Having access to a pool is always a bonus when you're vacationing, especially if you have kids in tow. Splish splash the days away at one of these houses with a pool in or near Toll Gate Shores:

  • Leading our list of cool pool escapes is "Charming Islamorada Beach And Canal House". Vacationing families will feel right at home here, with convenient amenities like on-site watersports and a toaster also at hand.
  • Another popular option is "Islamorada Beach House - Private Beach". There's plenty to love about this retreat besides its pool, such as childrens activities and a fridge.

What are the best large family vacation rentals in or near Toll Gate Shores?

Cousin Jimmy, Uncle Elijah ... You can add them to your invitation list when you book a large family vacation rental in or near Toll Gate Shores. Get all your loved ones under the same roof at one of these spacious hideaways:

  • With 3 bedrooms that sleep as many as 8 guests, "Water Front 3/3 Family And Boat Friendly Home" gives you space to reunite with friends or relatives. It's around 0.1 miles north of Toll Gate Shores and features amenities that'll keep your group happy, such as a porch and a fridge.
  • "Come Experience The Florida Keys At Sunset Cove" is another property the whole team will love. You'll be able to invite as many as 12 friends and family to this retreat which offers 4 bedrooms, a smart TV, a fridge and more. It's around 0.1 miles to the southwest of central Toll Gate Shores.

If you'd like to visit some family-friendly attractions close by, Theater of the Sea promises a fun day out for all.

Are there one-bedroom vacation rentals in or near Toll Gate Shores?

Often located in sought-after positions due to their compact size, a one-bedroom vacation rental is a great choice if it's just the two of you. Here's a quick taste of our range in or near Toll Gate Shores:

  • Take a peek at "Smart Room In Beautiful Florida Keys Home", a fantastic centrally located one-bedroom vacation property. A fireplace and a kitchen are just a few of the inclusions here.
  • Also within easy reach of the center of Toll Gate Shores, "Islamorada Haven On The Water" is another popular one-bedroom option. After a big day of exploring, come home and take advantage of a barbecue grill and off-street parking options.

Can I find two-bedroom vacation rentals in or near Toll Gate Shores?

Absolutely. From swish apartments to cozy cabin retreats, Vrbo offers a selection of great rentals. Small groups or families will adore these two-bedroom options in or near Toll Gate Shores:

  • With a swimming pool and a fireplace, "Aquamarine Oceanviewsept And Oct Flash" has all you need for an excellent stay. Settle in and then venture out and explore your surrounds.
  • "Off The Beaten Path In One Of Islamorada’s Hidden Gem Of A Community" is another lovely two-bedroom escape. It offers a kitchen, a balcony and loads more.