Longboat Key Vacation Rentals from $297: 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.

Check prices for these dates

In two weeks

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Our top choices for Longboat Key vacation rentals

A wooden pathway leading to a beach with lush greenery on either side.

1. Oceanfront Oasis – Longboat Key 226 by RVA

Longboat Key

Sherri G.

$245 nightly

Nov 19 - Nov 20

Total with taxes and fees

A wide sandy beach with clear turquoise water and a clear blue sky.

2. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key

Peter

$349 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden pathway leading to a beach with lush greenery and a clear sky.

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

Longboat Key

Kellie B.

$282 nightly

Nov 24 - Nov 25

Total with taxes and fees

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

Longboat Key

William

$258 nightly

Nov 22 - Nov 23

Total with taxes and fees

A beach with sand, sea, and sparse vegetation.

5. Vitamin Sea: Open November 20th - 26th!

Longboat Key

Jessica L.

$327 nightly

Dec 1 - Dec 2

Total with taxes and fees

6. Silver Sands Serenity – Unit 234 by RVA

Longboat Key

Tanya B.

$273 nightly

Nov 16 - Nov 17

Total with taxes and fees

7. Cozy Beach Studio – Silver Sands #251A by RVA

Longboat Key

Susan G.

$253 nightly

Nov 16 - Nov 17

Total with taxes and fees

8. Relax at Gulf – Silver Sands Resort #232, Longboat

Longboat Key

Gloria

$274 nightly

Nov 22 - Nov 23

Total with taxes and fees

9. Gulf Front Escape – Silver Sands #252 by RVA

Longboat Key

jeannie b.

$283 nightly

Nov 16 - Nov 17

Total with taxes and fees

A sandy beach path flanked by dense green foliage leading to the ocean.

10. Seaside Escape – Beach Castle #24 by RVA

Longboat Key

James

$258 nightly

Nov 17 - Nov 18

Total with taxes and fees

A beach with clear blue water and a sandy shore, framed by green foliage.

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

Longboat Key

Victoria F.

$303 nightly

Nov 17 - Nov 18

Total with taxes and fees

A beach at sunset with waves, a person walking, and a clear sky.

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

Longboat Key

william w.

$487 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

Longboat Key

Ann S.

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

14. Direct Oceanview on LBK!

Longboat Key

Ivan

$336 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Longboat Key

A guest from Cincinnati, OH

$254 nightly

Nov 18 - Nov 19

Total with taxes and fees

A beach with clear turquoise waters and a boat on the shore.

16. Renovated Beach Paradise. Ground Floor unit 64

Longboat Key

Jason W.

$335 nightly

Nov 16 - Nov 17

Total with taxes and fees

17. Poolside Peace – Silver Sands Resort #242 by RVA

Longboat Key

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful beach, I crowded and clean. Facilities are a little dated but well maintained and staff was great. Would have appreciated a grab bar in the shower."

EDWARD B.

$303 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beach with a palm tree, a sign, and a lifeguard stand.

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

Longboat Key

Charles J.

$298 nightly

Nov 16 - Nov 17

Total with taxes and fees

A sandy beach with a clear blue sky, a few umbrellas, and beach chairs.

19. Sun and Sea: Open Tomorrow Nite!

Longboat Key

Ashley G.

$253 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beach with a clear sky, sandy shore, and vegetation.

20. Sunny Daze: Open Nov 21st - 24th!

Longboat Key

Reuben T.

$356 nightly

Dec 2 - Dec 3

Total with taxes and fees

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Top Longboat Key Hotel Reviews

The St. Regis Longboat Key Resort

10/10 Excellent

"All the amenities and an incredible staff!!"

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8/10 Good

"Perfect location! You can walk right out to the beach from the property. The view was stunning, we had the most breathtaking views from our lanai every night. Close to Publix for ease of grocery shopping.Would stay again!"

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!"

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

10/10 Excellent

"The cottage and grounds were wonderful. Everything about the condo was great. Pool and beach were amazing. The only complaint I have is that it was late when we arrived & the grounds are dimly dark. The check in instructions said to locate the Key Pad, touch it, it would light up and you could punch in the code. It was not stated that the Key Pad would be on the door, and not on the exterior wall under the porch light, which was the only key pad we could see in the dark. The visible key pad, did not work. The host had sent us a message earlier that day, while we were flying, saying she would be out of town and if there were any issues to contact her son and gave us his number. I called her son, who was very nice, but was unfamiliar with the property so was unable to help. He noted he would try to get a hold of his Mom & would call us back. We also reached out to the main VRBO number and they were unable to help. After 20 minutes trying to access the cottage, my husband inadvertently touch the door, and the key pad under it lit up. We were tired and frustrated by this point. Better instructions for late night arrivals stating the key pad is not the one visible on the wall, but on the door, which couldn't be seen due to darkness would have saved us a lot of frustration."

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."

Price trends for vacation rentals in Longboat Key

Less expensive	More expensive	Next month
October	February	$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 $297 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. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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

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

5. Vitamin Sea: Open November 20th - 26th!

6. Silver Sands Serenity – Unit 234 by RVA

7. Cozy Beach Studio – Silver Sands #251A by RVA

8. Relax at Gulf – Silver Sands Resort #232, Longboat

9. Gulf Front Escape – Silver Sands #252 by RVA

10. Seaside Escape – Beach Castle #24 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. Gulf Views – Silver Sands #250, Longboat Key by RVA

14. Direct Oceanview on LBK!

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

16. Renovated Beach Paradise. Ground Floor unit 64

17. Poolside Peace – Silver Sands Resort #242 by RVA

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

19. Sun and Sea: Open Tomorrow Nite!

20. Sunny Daze: Open Nov 21st - 24th!

Find vacation rentals that suit your style

Top Longboat Key Hotel Reviews

The St. Regis Longboat Key Resort

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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