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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Longboat Key vacation rentals

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

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

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (86 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
Relax at Gulf – Silver Sands Resort #232, Longboat
A wide sandy beach with clear turquoise water and a clear blue sky.

2. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful property. Will definitely stay again."
United States
Tami T.
$405 nightly
The price is $453
Oct 25 - Oct 26
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
A wooden pathway leading to a beach with lush greenery on either side.

3. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (140 reviews)
"We loved it and recommend it and definitely plan another. Locals only lol."
United States
Kenneth
$301 nightly
The price is $336
Oct 18 - Oct 19
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 by RVA
A beach view with a golf course, palm trees, and a building with outdoor seating.

4. Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (73 reviews)
"Great place, close to the beach. Will visit again."
United States
Jason W.
Renovated Beach Paradise. Ground Floor unit 64
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, (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.
$279 nightly
The price is $311
Oct 18 - Oct 19
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA
A wooden pathway leading to a beach with lush greenery on either side.

6. 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.
$272 nightly
The price is $303
Oct 20 - Oct 21
Total with taxes and fees
Oceanfront Bliss–Longboat Key Beach 106 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

7. Silver Sands Serenity – Unit 234 by RVA

Silver Sands Serenity – Unit 234 by RVA
Longboat Key
9.4 out of 10, Exceptional, (35 reviews)
" Great location, office staff are very pleasant, room was very spacious with everything you need"
United States
GLENNA M.
$273 nightly
The price is $304
Oct 19 - Oct 20
Total with taxes and fees
Silver Sands Serenity – Unit 234 by RVA
A beach view with a golf course, palm trees, and a building with outdoor seating.

8. 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, (77 reviews)
"Enjoyed our stay!"
United States
Charles J.
$319 nightly
The price is $352
Oct 24 - Oct 25
Total with taxes and fees
Step from the Beach.Renovated ground Floor unit 63
A beach with clear turquoise water and a sandy shore.

9. 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, (94 reviews)
"The location of the condo is 10 out of 10. The views and beach access cannot be beat. We enjoyed the space and appreciated the small but functional kitchen. We even found some beach supplies and an umbrella in the closet! This is a very great space and location. We will be back!"
United States
Anthony B.
$356 nightly
The price is $392
Nov 3 - Nov 4
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.

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.
$308 nightly
The price is $344
Oct 26 - Oct 27
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA
A beach view from a balcony with a railing, ocean, and beach vegetation.

11. Silver Sands: November & December Availability!

Silver Sands: November & December Availability!
Longboat Key
10.0 out of 10, Exceptional, (101 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
$349 nightly
The price is $389
Nov 4 - Nov 5
Total with taxes and fees
Silver Sands: November & December Availability!
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.
$313 nightly
The price is $349
Oct 25 - Oct 26
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
A living room with a sofa, a coffee table, and a TV. There is a balcony with a view of the ocean.

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

Take a peek at awesome reviews 50 feet from the sand
Longboat Key
10.0 out of 10, Exceptional, (152 reviews)
"This location is one of our favorite vacation spots - we try to come back every spring. This room was recently renovated and looks great, and the view of the beach is very relaxing. The host is very experienced and makes this trip a breeze. We’ll be back!"
United States
Angie E.
$541 nightly
The price is $603
Nov 10 - Nov 11
Total with taxes and fees
Take a peek at awesome reviews 50 feet from the sand
A sandy beach path flanked by dense green foliage leading to the ocean.

14. 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.
$296 nightly
The price is $330
Oct 18 - Oct 19
Total with taxes and fees
Coastal Comfort – Beach Castle #26 by RVA
A wooden pathway leading to a beach with lush greenery and a clear sky.

15. Relax, Recharge & Repeat – Silver Sands #241 by RVA

Relax, Recharge & Repeat – Silver Sands #241 by RVA
Longboat Key
9.4 out of 10, Exceptional, (46 reviews)
"Great location! Beach steps away. Relaxing pool. Clean unit"
United States
Deborah F.
$359 nightly
The price is $400
Oct 23 - Oct 24
Total with taxes and fees
Relax, Recharge & Repeat – Silver Sands #241 by RVA
A beach with clear blue water and a sandy shore, framed by green foliage.

16. 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, (64 reviews)
"The view from the room was amazing. The entire property was very clean and well kept."
United States
Jane B.
$400 nightly
The price is $446
Oct 19 - Oct 20
Total with taxes and fees
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
A wooden pathway leading to a beach with lush greenery and a clear sky.

17. 1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (99 reviews)
"Great view, clean, beautiful!"
United States
Bethany
$338 nightly
The price is $376
Oct 29 - Oct 30
Total with taxes and fees
1BR Beach Getaway – Silver Sands #254 by RVA
A room with a large window overlooking a beach, a round table with chairs, and a wicker chair with a cushion.

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

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.2 out of 10, Wonderful, (89 reviews)
"Great location and great views!"
United States
Mark H.
$343 nightly
The price is $382
Oct 18 - Oct 19
Total with taxes and fees
The Beach on Longboat Key #227 Resort by RVA
A balcony with a view of a beach, a pool, and palm trees.

19. Direct Oceanview: Open October 26th - 29th!

Direct Oceanview: Open October 26th - 29th!
Longboat Key
10.0 out of 10, Exceptional, (137 reviews)
"the absolute best views and beyond better hosts"
United States
Ivan
$378 nightly
The price is $422
Oct 26 - Oct 27
Total with taxes and fees
Direct Oceanview: Open October 26th - 29th!
A beach with clear turquoise water and a sandy shore.

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

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (80 reviews)
"It was nice. Enjoyed being on the beach and having a feeling of spaciousness."
United States
Eloisa A.
$330 nightly
The price is $367
Oct 18 - Oct 19
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

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Everyone was kind, caring, friendly, attentive to your needs. They were on top of it. Made it feel you were special. They all were kind. Down to earth. Cleanliness was superior from top to bottom. It was awesome even down to the food. 10/10 stars!!! Definitely going back!"
Joy 5-night trip
Posted 2 days ago
Zota Beach Resort

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
October
February
$394
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 $336 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 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.