Longboat Key Vacation Rentals from $338: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Longboat Key has to offer?

Tropical Villas of Venice Beach : This vacation home rental near Longboat Key is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

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Our top choices for Longboat Key vacation rentals

A pool area with a view of the beach, surrounded by palm trees and greenery.

1. Oceanfront Oasis – Longboat Key 226 by RVA

Longboat Key

Sherri G.

$325 nightly

Nov 19 - Nov 20

Total with taxes and fees

A resort with a swimming pool, beach, and ocean view.

2. Affordable Beach Studio – Silver Sands #257A by RVA

Longboat Key

Stacey K.

$252 nightly

Nov 4 - Nov 5

Total with taxes and fees

A living room with a sofa, coffee table, and a balcony with a view of the sea and palm trees.

3. Best views of the beach from your balcony Unit 301

Longboat Key

Anthony B.

A bedroom with a bed, a desk, a sofa, a ceiling fan, and a view of the beach through the sliding doors.

4. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key

Peter

$384 nightly

Nov 4 - Nov 5

Total with taxes and fees

5. Silver Sands 1BR – Gulfside Comfort #255 by RVA

Longboat Key

Daniela L.

A beach view from a balcony with a railing, ocean, and beach vegetation.

6. New Opening: Sunday - Friday!

Longboat Key

"Just got back from our long weekend trip to Longboat Key. Had a marvelous stay in the Vitamin Sea property. Everything was just perfect - really nice unit with all the necessities already stocked, steps from a beautiful beach and gorgeous sunsets, and great amenities (to include miniature golf)! Great pool for morning swims. Our host, Heidi, was a gem! Easy reservation/check-in and always making sure we had everything we needed. She even surprised us with a shell ornament gift and cinnamon...

Richard

$274 nightly

Nov 4 - Nov 5

Total with taxes and fees

7. Gulfside Resort – Silver Sands #241A by RVA

Longboat Key

Kellie B.

$266 nightly

Nov 13 - Nov 14

Total with taxes and fees

8. Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

Longboat Key

William

A room with a large window overlooking a beach, a round table with chairs, and a wicker chair with a cushion.

9. The Beach on Longboat Key #227 Resort by RVA

Longboat Key

Mark H.

10. Silver Sands #245A Resort by RVA

Longboat Key

donald m.

A beach with white sand and a clear blue sky. There are blue lounge chairs aligned in rows.

11. Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Longboat Key

Victoria F.

$302 nightly

Nov 15 - Nov 16

Total with taxes and fees

A living room with a sofa, a coffee table, and a TV. There is a balcony with a view of the ocean.

12. Take a peek at awesome reviews 50 feet from the sand

Longboat Key

"My family and I had a great stay at the property. The proximity to the beach was great for our family and allowed for easy breaks during the day as it was only a minute walk to the beach. Easy drives to Sarasota and Anna Maria Island made for fun day trips with little work to get there. Would recommend for those wanting a relaxing stay with easy beach access and desiring to be outside of the highly tourist traffic. Thanks for a great stay."

Jason C.

$540 nightly

Nov 10 - Nov 11

Total with taxes and fees

A balcony with a view of a beach, a pool, and palm trees.

13. Direct Oceanview on LBK: Open Nov 9th & 10th!

Longboat Key

Ivan

$313 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern living room with a sofa, chairs, a coffee table, and a TV. There is a balcony with a view of the outdoors.

14. Drift & Dune – Longboat Beachfront #101 RVA

Longboat Key

Bailey B.

$275 nightly

Nov 4 - Nov 5

Total with taxes and fees

A room with a balcony overlooking a beach, featuring a table with two blue placemats, a chair, and a bookshelf.

15. Gulf Views – Silver Sands #250, Longboat Key by RVA

Longboat Key

Ann S.

$351 nightly

Nov 13 - Nov 14

Total with taxes and fees

A living room with a ceiling fan, a television, a sofa, a coffee table, and a window with blinds.

16. 1BD/1BA Silver Sands Gulf Front w/Garden View

Longboat Key

$311 nightly

Nov 6 - Nov 7

Total with taxes and fees

A beach view with a golf course, palm trees, and a building with outdoor seating.

17. Step from the Beach.Renovated ground Floor unit 63

Longboat Key

Charles J.

$334 nightly

Nov 22 - Nov 23

Total with taxes and fees

18. Coastal Comfort – Silver Sands Resort #233 by RVA

Longboat Key

Emily

$295 nightly

Nov 18 - Nov 19

Total with taxes and fees

A beachside area with palm trees, lounge chairs, and a view of the ocean.

19. Beachfront Bliss on Longboat Key- Steps to the sand

Longboat Key

Pacey D.

$350 nightly

Nov 4 - Nov 5

Total with taxes and fees

20. Sunny Daze on LBK: Open Nov 12th & 13th!

Longboat Key

Reuben T.

$305 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Top Longboat Key Hotel Reviews

Fall sale ready for a luxury 5-floor penthouse 60 ft from water,

10/10 Excellent

"My Husband and I stayed here at this beautiful oceanfront condo at Longboat Key the last week of October 2026. It was perfect in every way. The space was just right for us. We Loved waking up to the Oceanfront views and being right on the water made it extra special. It was comfortable, inviting and the perfect place to unwind and enjoy the beauty of Longboat Key. We couldn't have asked for a better stay and would happily return. Highly recommend!"

Take a peek at awesome reviews 50 feet from the sand

10/10 Excellent

"The condo was clean and tastefully furnished. The bedroom was luxurious with a comfortable mattress and high-end bedding. The view was stunning and we were steps from the beach and the pool as well. We loved how peaceful Longboat Key is. Our host was helpful and communicative. We would definitely stay at this property again!"

Direct Oceanview: Open October 26th - 29th!

10/10 Excellent

"Heidi was the best VRBO host we’ve ever had. She has thought of every comfort on property and her communication is superb, always friendly, caring and helpful. We loved the second floor balcony for viewing the gulf and the ease of being on the beach and near the pool. We hope to stay at one of her properties on Longboat Key again."

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

8/10 Good

"The ocean front balcony and the property location was excellent, as well as the regularly maintained grounds left everything very clean and neat. The inside of the rental was much smaller than anticipated and proved very difficult to place our luggage and unpack anything. The bed was extremely hard and bery cramped. On a plus side, the private balcony views and the water pressure in the shower were amazing! Communication, the parking lot and check-in were also great."

Price trends for vacation rentals in Longboat Key

Less expensive	More expensive	This month	Next month
October	February	$394	$429

Month	Price
January	$430
February	$539
March	$484
April	$441
May	$409
June	$463
July	$458
August	$384
September	$374
October	$371
November	$394
December	$429

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Longboat Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Longboat Key

Everything you need to know about Longboat Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Longboat Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Longboat Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Longboat Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Longboat Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $338 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Longboat Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Longboat Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Longboat Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the popular beaches in Longboat Key. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Longboat Key has to offer?

Tropical Villas of Venice Beach: This vacation home rental near Longboat Key is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Longboat Key?

Choose from 17 Expedia vacation rentals in Longboat Key for a memorable vacation.

What can I see and do in Longboat Key?

Longboat Key Beaches and Jewfish Key are a couple of lovely local spots to get outside and enjoy nature. Lido Beach and Siesta Key Beach are other popular places to visit in the area.

What are vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

Longboat Key Vacation Rentals

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Check prices for these dates

Our top choices for Longboat Key vacation rentals

1. Oceanfront Oasis – Longboat Key 226 by RVA

2. Affordable Beach Studio – Silver Sands #257A by RVA

3. Best views of the beach from your balcony Unit 301

4. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

5. Silver Sands 1BR – Gulfside Comfort #255 by RVA

6. New Opening: Sunday - Friday!

7. Gulfside Resort – Silver Sands #241A by RVA

8. Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

9. The Beach on Longboat Key #227 Resort by RVA

10. Silver Sands #245A Resort by RVA

11. Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

12. Take a peek at awesome reviews 50 feet from the sand

13. Direct Oceanview on LBK: Open Nov 9th & 10th!

14. Drift & Dune – Longboat Beachfront #101 RVA

15. Gulf Views – Silver Sands #250, Longboat Key by RVA

16. 1BD/1BA Silver Sands Gulf Front w/Garden View

17. Step from the Beach.Renovated ground Floor unit 63

18. Coastal Comfort – Silver Sands Resort #233 by RVA

19. Beachfront Bliss on Longboat Key- Steps to the sand

20. Sunny Daze on LBK: Open Nov 12th & 13th!

Find vacation rentals that suit your style

Top Longboat Key Hotel Reviews

Fall sale ready for a luxury 5-floor penthouse 60 ft from water,

Price trends for vacation rentals in Longboat Key

Find out more about Longboat Key

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

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