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

Longboat Key Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Longboat Key vacation rentals

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

1. 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.
$292 nightly
The price is $326
Sep 7 - Sep 8
Total with taxes and fees
Affordable Beach Studio – Silver Sands #257A by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

2. 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
$321 nightly
The price is $357
Sep 13 - Sep 14
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
A wide sandy beach with clear turquoise water and a clear blue sky.

3. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (99 reviews)
"Very good"
United States
Graciela Maria
$349 nightly
The price is $389
Sep 4 - Sep 5
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
A sandy beach path flanked by dense green foliage leading to the ocean.

4. 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
Seaside Escape – Beach Castle #24 by RVA
A beach with clear turquoise water and a sandy shore.

5. Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (83 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.
$281 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
A sandy beach path flanked by dense green foliage leading to the ocean.

6. Coastal Comfort – Beach Castle #26 by RVA

Coastal Comfort – Beach Castle #26 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"Stayed 5 days. Lovely condo, everything we needed was there."
United States
Grace E.
Coastal Comfort – Beach Castle #26 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

7. 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
$344 nightly
The price is $383
Sep 7 - Sep 8
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA
A beach view from a balcony with a railing, ocean, and beach vegetation.

8. Sunny Days on LBK: Open Wed, Sept 9th!

Sunny Days on LBK: Open Wed, Sept 9th!
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
$306 nightly
The price is $340
Sep 30 - Oct 1
Total with taxes and fees
Sunny Days on LBK: Open Wed, Sept 9th!
A wooden pathway leading to a beach with lush greenery and a clear sky.

9. 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.
$310 nightly
The price is $346
Sep 7 - Sep 8
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

10. 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
$301 nightly
The price is $335
Sep 7 - Sep 8
Total with taxes and fees
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
A wooden pathway leading to a beach with lush greenery and a clear sky.

11. Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (63 reviews)
"Liked"
United States
jacquelynn b.
$302 nightly
The price is $336
Sep 9 - Sep 10
Total with taxes and fees
Silver Sands #245A Resort by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

12. 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.
$312 nightly
The price is $348
Sep 7 - Sep 8
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

13. 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.
$377 nightly
The price is $420
Sep 10 - Sep 11
Total with taxes and fees
Gulf Views – Silver Sands #250, Longboat Key by RVA
A sandy beach path flanked by dense green foliage leading to the ocean.

14. 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.
Gulf Getaway – Beach Castle #12 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

15. 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
$337 nightly
The price is $375
Sep 7 - Sep 8
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

16. 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)
"We had the most wonderful stay despite the cold temps for most it! The staff at our location are above and beyond to make sure you have everything you need! Highly recommend!"
United States
Sahra S.
$304 nightly
The price is $339
Sep 7 - Sep 8
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
A wooden pathway leading to a beach with lush greenery on either side.

17. Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (108 reviews)
"It was a great location. It had a nice pool area, plenty of beach chairs and beach goodies to use."
United States
Laurie L.
Oceanfront Bliss–Longboat Key Beach 106 by RVA
A beach with clear turquoise water and a sandy shore.

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

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (93 reviews)
"Everything was great "
United States
kirt v.
$366 nightly
The price is $403
Sep 17 - Sep 18
Total with taxes and fees
Best views of the beach from your balcony Unit 301
A wooden pathway leading to a beach with lush greenery and a clear sky.

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

Coastal Comfort – Silver Sands Resort #233 by RVA
Longboat Key
8.8 out of 10, Excellent, (35 reviews)
"3rd time here already booked another trip. So easy! Love it here!"
United States
Emily
$297 nightly
The price is $330
Sep 8 - Sep 9
Total with taxes and fees
Coastal Comfort – Silver Sands Resort #233 by RVA
A modern living room with a glass coffee table, a sofa, a TV, and a balcony with outdoor furniture.

20. Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony

Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony
Longboat Key
9.8 out of 10, Exceptional, (147 reviews)
"Great location, great property! "
United States
Chelsy K.
Beachfront Escape – Private Balcony, Gulf Views, No Street to Cross, Watch the Sunset from Your Balcony
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

The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA

10/10 Excellent
"Gorgeous view of beach from 2nd floor, although a middle unit would have been nicer than end by trees. Fantastic amount of kitchen amenities but glad I brought a larger coffee pot. Plenty of towels and bed linen available with very comfortable murphy bed mattress. Provisions for the beach was exceptional. Would definitely stay here again."
Cindy D. 4-night trip
Posted 20 hours ago
The Beach on Longboat Key #227 Resort by RVA

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 $312 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 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 21 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.