A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Longboat Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Longboat Key vacation rentals

On the beach, beach umbrellas

1. 1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (98 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$334 nightly
The price is $372
Sep 27 - Sep 28
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
On the beach, beach umbrellas

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

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (89 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: What a great experience beautiful room,very clean,best location,private, very clean,all staff was polite and helpful"
United States
Anonymous traveler
$342 nightly
The price is $381
Sep 16 - Sep 17
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA
Beach nearby

3. Gulf Getaway – Beach Castle #12 by RVA

Gulf Getaway – Beach Castle #12 by RVA
Longboat Key
9.6 out of 10, Exceptional, (43 reviews)
"Amazing resort and housing. Will be back and enjoying all that Beach Castle has to offer!"
United States
Blake S.
$485 nightly
The price is $540
Sep 13 - Sep 14
Total with taxes and fees
Gulf Getaway – Beach Castle #12 by RVA
On the beach, beach umbrellas

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

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (109 reviews)
"This place is a little dated but extremely clean! We will stay here again! The location to the beach was unmatchable!"
United States
Jessica C.
$345 nightly
The price is $385
Sep 16 - Sep 17
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA
On the beach

5. Sea Grape Inn #1- Beachfront Property

Sea Grape Inn #1- Beachfront Property
Longboat Key
10.0 out of 10, Exceptional, (17 reviews)
"The property is in excellent condition. The property manager is exceptionally responsive. The location is great and the screen porch is epic!"
United States
Molly V.
Sea Grape Inn #1- Beachfront Property
On the beach, beach umbrellas

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

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (83 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$309 nightly
The price is $344
Sep 13 - Sep 14
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
On the beach, beach umbrellas

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

Gulf Views – Silver Sands #250, Longboat Key by RVA
Longboat Key
9.0 out of 10, Wonderful, (81 reviews)
"The host staff were very helpful."
United States
Ann S.
$359 nightly
The price is $400
Sep 13 - Sep 14
Total with taxes and fees
Gulf Views – Silver Sands #250, Longboat Key by RVA
Beach nearby

8. Beach Castle Bliss #22 by RVA

Beach Castle Bliss #22 by RVA
Longboat Key
9.6 out of 10, Exceptional, (51 reviews)
"The walks to the bay and Gulf were shorter than we anticipated (bonus: a couple of restaurants are a short walk away, too). Sunrise over the bay just a few steps from our unit, and sunsets over the Gulf just across the street. The unit itself was clean, comfortable, with plenty of space. And the pool area is very well maintained. Overall, it's exactly what we wanted from our Longboat Key getaway."
United States
Robert S.
$450 nightly
The price is $501
Sep 13 - Sep 14
Total with taxes and fees
Beach Castle Bliss #22 by RVA
On the beach, beach umbrellas

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

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (82 reviews)
"Lovely hotel right on the Gulf. Steps directly to the beach. Beautiful sunsets."
United States
SUSAN C.
$291 nightly
The price is $325
Sep 16 - Sep 17
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA
On the beach, beach umbrellas

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

Gulfside Resort – Silver Sands #241A by RVA
Longboat Key
8.4 out of 10, Very Good, (51 reviews)
"Beach is beautiful, location is great. Room was clean. Rhe bed"
United States
Kellie B.
$309 nightly
The price is $345
Sep 16 - Sep 17
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
On the beach, beach umbrellas

11. Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (69 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our experience was fantastic and everything was just as described. The place was clean and close to everything."
United States
Chris C.
$299 nightly
The price is $333
Sep 16 - Sep 17
Total with taxes and fees
Bright Beach Studio – Silver Sands #255A by RVA
Beach nearby

12. Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (51 reviews)
"Loved staying here"
United States
James
$298 nightly
The price is $332
Sep 27 - Sep 28
Total with taxes and fees
Seaside Escape – Beach Castle #24 by RVA
On the beach, sun loungers, beach towels

13. Seashells by the Seashore: Open Sept 21st & 22nd!

Seashells by the Seashore: Open Sept 21st & 22nd!
Longboat Key
10.0 out of 10, Exceptional, (97 reviews)
"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...
United States
Richard
$347 nightly
The price is $386
Sep 21 - Sep 22
Total with taxes and fees
Seashells by the Seashore: Open Sept 21st & 22nd!
On the beach

14. Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (84 reviews)
"The cabana was a fantastic place to escape. It had easy access to both the beach and the pool. My kids loved every moment there."
United States
Roxana P.
$267 nightly
The price is $298
Sep 23 - Sep 24
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
On the beach, beach umbrellas

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

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Longboat Key
8.2 out of 10, Very Good, (10 reviews)
"Nice place, clean, conveniently located, right on the beach, very helpful/friendly manager. We didn’t use the pool but it was clean and well taken care of, also heated. Beach was awesome, soft clean sand, clear water. Would like to stay here again."
United States
William
$300 nightly
The price is $334
Sep 14 - Sep 15
Total with taxes and fees
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
On the beach, beach umbrellas

16. Silver Sands #245S Resort by RVA

Silver Sands #245S Resort by RVA
Longboat Key
9.0 out of 10, Wonderful, (31 reviews)
"Location, pool out the patio door, clean beach, just steps out door to ocean. Great staff at check-in & out. Clean grounds"
United States
Nancy J.
$501 nightly
The price is $559
Sep 14 - Sep 15
Total with taxes and fees
Silver Sands #245S Resort by RVA
On the beach, beach umbrellas

17. Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
Longboat Key
8.8 out of 10, Excellent, (44 reviews)
"Beach was perfect!"
United States
Carmela D.
$309 nightly
The price is $344
Sep 14 - Sep 15
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
On the beach, beach umbrellas

18. Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (64 reviews)
"Would def stay here again!"
United States
Tammie and David
$303 nightly
The price is $338
Sep 16 - Sep 17
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
TV

19. 2BR Gulfside Paradise – Longboat Key by RVA

2BR Gulfside Paradise – Longboat Key by RVA
Longboat Key
9.8 out of 10, Exceptional, (87 reviews)
"Beautiful location- perfect for the whole family."
United States
Dana B.
$466 nightly
The price is $520
Sep 29 - Sep 30
Total with taxes and fees
2BR Gulfside Paradise – Longboat Key by RVA
On the beach

20. Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (76 reviews)
"The view and beach access was amazing. Loved our stay. "
United States
Julie F.
$330 nightly
The price is $368
Sep 14 - Sep 15
Total with taxes and fees
Newly Renovated 1BR – Cabana Beach #5 RVA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Longboat Key Hotel Reviews

End of summer sale Take a peek awesome reviews 50 feet from sand

End of summer sale Take a peek awesome reviews 50 feet from sand

10/10 Excellent
"What a view! It was just breathtaking! Jim is wonderful to work with and communicates very efficiently and promptly. We arrived a little early, and I checked to see if the condo would possibly be cleaned and ready. Since it was we were we were able to check right in. Big thank you for that! We would definitely stay here again!"
Denise C. 4-night trip
Posted 2 days ago
End of summer sale Take a peek awesome reviews 50 feet from sand

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
This month
Next month
October
February
$374
$371
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 $292 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.

Explore a world of travel with Expedia

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?

Siesta Key Island Rentals: This vacation home rental near Longboat Key comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Longboat Key?

Choose from 19 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. Siesta Key Beach and Lido 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.