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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (83 reviews)
"Lovely hotel right on the Gulf. Steps directly to the beach. Beautiful sunsets."
United States
SUSAN C.
$276 nightly
The price is $310
Sep 28 - Sep 29
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. Silver Sands #247S – 2BR/2BA Resort, Sleeps 6

Silver Sands #247S – 2BR/2BA Resort, Sleeps 6
Longboat Key
9.4 out of 10, Exceptional, (6 reviews)
"Loved my stay! Very clean and welcoming! "
United States
Nichole H.
$438 nightly
The price is $492
Oct 2 - Oct 3
Total with taxes and fees
Silver Sands #247S – 2BR/2BA Resort, Sleeps 6
A wooden pathway leading to a beach with lush greenery and a clear sky.

3. 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
$281 nightly
The price is $314
Sep 28 - Sep 29
Total with taxes and fees
Silver Sands 1BR – Gulfside Comfort #255 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

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

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (84 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
$281 nightly
The price is $314
Sep 29 - Sep 30
Total with taxes and fees
Relax at Gulf – Silver Sands Resort #232, Longboat
A wooden pathway leading to a beach with lush greenery and a clear sky.

5. 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.
$270 nightly
The price is $302
Sep 28 - Sep 29
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
A sandy beach path flanked by dense green foliage leading to the ocean.

6. 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
$279 nightly
The price is $313
Sep 28 - Sep 29
Total with taxes and fees
Seaside Escape – Beach Castle #24 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

7. Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (64 reviews)
"Liked"
United States
jacquelynn b.
$271 nightly
The price is $303
Sep 28 - Sep 29
Total with taxes and fees
Silver Sands #245A Resort by RVA
A sandy beach path flanked by dense green foliage leading to the ocean.

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.
$431 nightly
The price is $484
Sep 28 - Sep 29
Total with taxes and fees
Beach Castle Bliss #22 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

9. 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
$285 nightly
The price is $319
Oct 2 - Oct 3
Total with taxes and fees
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
A beach with clear turquoise water and a sandy shore.

10. 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.
$266 nightly
The price is $297
Oct 4 - Oct 5
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

11. 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
$312 nightly
The price is $349
Sep 28 - Sep 29
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.

12. 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
$264 nightly
The price is $296
Sep 29 - Sep 30
Total with taxes and fees
Coastal Comfort – Silver Sands Resort #233 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

13. 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.
$295 nightly
The price is $331
Oct 1 - Oct 2
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
A beach with clear blue water and a sandy shore, framed by green foliage.

14. Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Longboat Key
9.2 out of 10, Wonderful, (63 reviews)
"The view from the room was amazing. The entire property was very clean and well kept."
United States
Jane B.
$375 nightly
The price is $421
Sep 29 - Sep 30
Total with taxes and fees
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
A sandy beach path flanked by dense green foliage leading to the ocean.

15. 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.
$468 nightly
The price is $525
Sep 28 - Sep 29
Total with taxes and fees
Gulf Getaway – Beach Castle #12 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

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.
$421 nightly
The price is $473
Sep 28 - Sep 29
Total with taxes and fees
Silver Sands #245S Resort by RVA
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

Step from the Beach.Renovated ground Floor unit 63
Longboat Key
9.4 out of 10, Exceptional, (76 reviews)
"Enjoyed our stay!"
United States
Charles J.
$282 nightly
The price is $313
Sep 28 - Sep 29
Total with taxes and fees
Step from the Beach.Renovated ground Floor unit 63
A wooden pathway leading to a beach with lush greenery on either side.

18. 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.
$259 nightly
The price is $290
Sep 28 - Sep 29
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA
A modern living room with a balcony overlooking the sea, a flat-screen TV, a sofa, and a coffee table.

19. Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (119 reviews)
"TCI is a great place to stay. Close to the beach, grocery store, shopping and walking paths. The condo was very clean and has all the amenities needed. The staff if very approachable and easy to connect with for any questions. This is our 2nd stay and we will return."
United States
Anonymous traveler
$326 nightly
The price is $360
Oct 4 - Oct 5
Total with taxes and fees
Sunset and beach view from your balcony Unit 403
A wooden pathway leading to a beach with lush greenery and a clear sky.

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

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (110 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.
$324 nightly
The price is $364
Sep 29 - Sep 30
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by 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

Island Time: Open Next Week!

Island Time: Open Next Week!

10/10 Excellent
"If you are looking for a great experience at Longboat Key. This is it. Heidi, the host was great. She was easy and quick to respond to any and all questions. She even sent cake for my birthday (Thanks again). The condo location is outstanding, right on the beach and our view was phenomenal. We had the best sunsets each night. The condo was well maintained and equipped with all your basic needs. Would highly recommend and hope to stay again."
Jennifer B. 4-night trip
Posted 3 days ago
Island Time: Open Next Week!

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
October
February
$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 $305 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?

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 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. 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.