Luxury Vacation Rentals in Longboat Key

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 6 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Longboat Key

Luxury Beachfront Retreat on Longboat Key

2 bedrooms•2 baths

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New

~$235 less than other sites

5272 Gulf of Mexico

3 bedrooms•3 baths

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New

~$680 less than other sites

Luxury Beachfront Retreat Pool Game Room

5 bedrooms•3.5 baths

•

New

~$745 less than other sites

Canalfront Retreat, Pool, Dock & Putting Green

3 bedrooms•2.5 baths

•

New

~$90 less than other sites

Pastel Palms, Resort Pool, Hot Tub & Sport Court

4 bedrooms•2 baths

•

New

~$95 less than other sites

Manatee Cove

4 bedrooms•5 baths

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New

~$385 less than other sites

Welcome to Longboat Key

Elevate your beach escape with Wander on Longboat Key. Our luxury vacation rentals in Longboat Key combine five-star standards with the privacy of a beautifully designed home, so every moment feels effortless.

Choose from serene beachfront and bay-view stays featuring open-plan living, chef-ready kitchens, plush suites, and generous outdoor lounges made for sunset unwinding. Expect ultra fast WiFi, inspiring views, pristine cleaning, and 24/7 concierge service in every home.

Plan a workcation, a family gathering, or a peaceful reset with confidence. With Wander, what you see is exactly what you get.

Destinations near Longboat Key

Available soon in Longboat Key

Canalfront Retreat, Pool, Dock & Putting Green

3 bedrooms•2.5 baths

•

New

~$90 less than other sites

Pastel Palms, Resort Pool, Hot Tub & Sport Court

4 bedrooms•2 baths

•

New

~$95 less than other sites

Featured vacation rentals in Longboat Key

Luxury Beachfront Retreat Pool Game Room

5 bedrooms•3.5 baths

•

New

~$745 less than other sites

Highlights in Longboat Key

Discover a tranquil barrier island paradise boasting pristine white-sand beaches, lush nature preserves, and refined coastal charm on Florida's Gulf Coast.

Whitney Beach

Joan M. Durante Community Park

Beer Can Island (Greer Island)

Quick Point Nature Preserve

Mote Marine Laboratory & Aquarium

St. Armands Circle

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Longboat Key

Luxury Beachfront Retreat on Longboat Key

2 bedrooms•2 baths

•

New

~$235 less than other sites

5272 Gulf of Mexico

3 bedrooms•3 baths

•

New

~$680 less than other sites

Luxury Beachfront Retreat Pool Game Room

5 bedrooms•3.5 baths

•

New

~$745 less than other sites

Canalfront Retreat, Pool, Dock & Putting Green

3 bedrooms•2.5 baths

•

New

~$90 less than other sites

Pastel Palms, Resort Pool, Hot Tub & Sport Court

4 bedrooms•2 baths

•

New

~$95 less than other sites

Manatee Cove

4 bedrooms•5 baths

•

New

~$385 less than other sites

View all homes

Most popular amenities for vacation rentals in Longboat Key

Other popular amenities & vacation types in Longboat Key

Family vacation rentals in Longboat Key

Large group vacation rentals in Longboat Key

Discover more of Longboat Key

Gulf-to-bay beauty defines Longboat Key, a slender barrier island with quiet stretches of powder-soft sand and calm, turquoise water. Sunrises over Sarasota Bay and glowing Gulf sunsets frame unhurried days on the shoreline or bike rides along palm-lined roads.

Stroll the mangrove boardwalks at Joan M. Durante Park, paddle quiet canals, then slip over the bridge to St. Armands Circle and Sarasota’s arts for a change of pace. Seclusion pairs with refinement here, from championship golf and premier tennis to boutique shopping and breezy waterfront dining.

That blend is why Wander's luxury vacation rentals in Longboat Key are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Longboat Key

Why should I book a Wander in Longboat Key over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Longboat Key delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Longboat Key?

Some of our most popular vacation rentals in Longboat Key include Luxury Beachfront Retreat on Longboat Key, 5272 Gulf of Mexico, and Luxury Beachfront Retreat~Pool~Game Room~Sleeps 16. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Longboat Key?

Wander offers 6 vacation rentals in Longboat Key, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Longboat Key?

You can check-in to Wander vacation rentals in Longboat Key after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Longboat Key have WiFi access?

Yes. Every Wander home in Longboat Key has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.