Longboat Key Vacation Rentals

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Our top choices for Longboat Key vacation rentals

Gulfside Resort – Silver Sands #241A by RVA

Gulfside Resort – Silver Sands #241A by RVA
Longboat Key
8.4 out of 10, Very Good, (47 reviews)
"We enjoyed this fun spot with private beach, pool, and more!"
United States
Willow C.
$286 nightly
The price is $319
Jan 31 - Feb 1
Total with taxes and fees
Gulfside Resort – Silver Sands #241A by RVA

Gulf Getaway – Beach Castle #12 by RVA

Gulf Getaway – Beach Castle #12 by RVA
Longboat Key
9.6 out of 10, Exceptional, (39 reviews)
"Lovely place to stay. Beautifully decorated! Beach chairs, umbrellas, and beach tables provided and just a short walk to the beach. Quick response time from the rental company when we had questions. Shopping and restaurants are just a short drive away. Wonderful place to stay. "
United States
Alisa O.
$329 nightly
The price is $367
Jan 31 - Feb 1
Total with taxes and fees
Gulf Getaway – Beach Castle #12 by RVA

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
9.0 out of 10, Wonderful, (64 reviews)
"This was a solo mom-cation. The room was clean and well stocked. The bathroom had fresh towels. I was seconds from sitting on the beach with a cold beer and no kids. It was perfect. "
United States
Blake M.
$280 nightly
The price is $312
Jan 31 - Feb 1
Total with taxes and fees
Bright Beach Studio – Silver Sands #255A by RVA

Coastal Comfort – Silver Sands Resort #233 by RVA

Coastal Comfort – Silver Sands Resort #233 by RVA
Longboat Key
8.8 out of 10, Excellent, (31 reviews)
"Great location. Friendly staff."
United States
David
$288 nightly
The price is $321
Jan 31 - Feb 1
Total with taxes and fees
Coastal Comfort – Silver Sands Resort #233 by RVA

Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen

Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen
Longboat Key
9.8 out of 10, Exceptional, (259 reviews)
"Very clean and “homey”. Access to the beach is so easy and close. Quaint and quiet with great access to the rest of the island. The Host communicated well and made sure our stay was everything we hoped for. "
United States
R. Brian L.
$364 nightly
The price is $407
Feb 1 - Feb 2
Total with taxes and fees
Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen

Gulfside Getaway – Silver Sands Resort #235 by RVA

Gulfside Getaway – Silver Sands Resort #235 by RVA
Longboat Key
8.8 out of 10, Excellent, (30 reviews)
"Very relaxing"
United States
Susan D.
$375 nightly
The price is $418
Jan 31 - Feb 1
Total with taxes and fees
Gulfside Getaway – Silver Sands Resort #235 by RVA

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

Relax, Recharge & Repeat – Silver Sands #241 by RVA
Longboat Key
9.4 out of 10, Exceptional, (40 reviews)
"Great beach view. Clean beautiful place."
United States
Brent N.
$334 nightly
The price is $372
Jan 31 - Feb 1
Total with taxes and fees
Relax, Recharge & Repeat – Silver Sands #241 by RVA

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (76 reviews)
"Perfect for our family."
United States
Kayla c.
$336 nightly
The price is $374
Feb 4 - Feb 5
Total with taxes and fees
Drift & Dune – Longboat Beachfront #101 RVA

2BR Gulfside Paradise – Longboat Key by RVA

2BR Gulfside Paradise – Longboat Key by RVA
Longboat Key
9.8 out of 10, Exceptional, (75 reviews)
"Very clean "
United States
Lana
$429 nightly
The price is $478
Jan 31 - Feb 1
Total with taxes and fees
2BR Gulfside Paradise – Longboat Key by RVA

Coastal Comfort - Beach Castle #23 by RVA

Coastal Comfort - Beach Castle #23 by RVA
Longboat Key
10.0 out of 10, Exceptional, (58 reviews)
"Amazing family vacation and loved the location!"
United States
Kaitlin M.
$400 nightly
The price is $446
Feb 6 - Feb 7
Total with taxes and fees
Coastal Comfort - Beach Castle #23 by RVA

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very Good, (73 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
$310 nightly
The price is $348
Feb 25 - Feb 26
Total with taxes and fees
Beachfront Studio – Cabana #5B by RVA

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, (60 reviews)
"Super beautiful beach and heated pool. So nice. My room had zero view but it was fine. You are there for beach. Not the room. It was clean. Pool was so clear and warm! Coffee pot, refrig and micro all good. Bed was comfy. No sink in apt except bathroom sink. Awkward. But fine. Sunrise to sunset . "
United States
Pamela
$405 nightly
The price is $452
Feb 21 - Feb 22
Total with taxes and fees
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
7.0 out of 10, Good, (2 reviews)
"Location was perfect for the beach access we were looking for. The unit was small with a few minor glitches, but it was clean.The property and pool were well mantained and there were no issues with check-in."
United States
GLEN R.
$355 nightly
The price is $396
Feb 1 - Feb 2
Total with taxes and fees
Beachfront Bliss on Longboat Key- Steps to the sand

Right on the beach.Renovated ground Floor unit 63.

Right on the beach.Renovated ground Floor unit 63.
Longboat Key
9.4 out of 10, Exceptional, (59 reviews)
"Excellent, clean, and friendly"
United States
John G.
$291 nightly
The price is $322
Feb 9 - Feb 10
Total with taxes and fees
Right on the beach.Renovated ground Floor unit 63.

Sea Grape Inn #6- Beachfront Property

Sea Grape Inn #6- Beachfront Property
Longboat Key
10.0 out of 10, Exceptional, (31 reviews)
"Sea, sand, fun and great accommodations!"
United States
Patti D.
$687 nightly
The price is $757
Jan 31 - Feb 1
Total with taxes and fees
Sea Grape Inn #6- Beachfront Property

Silver Sands 256 on LBK: Open Tomorrow, $175/nt + Fees!

Silver Sands 256 on LBK: Open Tomorrow, $175/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (86 reviews)
"The perfect beach cottage for our wedding anniversary. We had everything we needed including beautiful weather ."
United States
Julie Q.
$475 nightly
The price is $531
Feb 13 - Feb 14
Total with taxes and fees
Silver Sands 256 on LBK: Open Tomorrow, $175/nt + Fees!

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (100 reviews)
"Perfect for our family "
United States
Alan B.
$339 nightly
The price is $379
Feb 4 - Feb 5
Total with taxes and fees
Gulf Front Escape – Silver Sands #252 by RVA

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, (110 reviews)
"Gorgeous view and comfortable interior. Great beach access and good pool. "
United States
Tanya M.
$589 nightly
The price is $650
Feb 7 - Feb 8
Total with taxes and fees
Sunset and beach view from your balcony Unit 403

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, (42 reviews)
"Enjoyed our stay"
United States
Susan C.
$375 nightly
The price is $419
Feb 12 - Feb 13
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful location and the beach is amazing "
United States
Heather A.
$461 nightly
The price is $514
Feb 10 - Feb 11
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
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

Price trends for vacation rentals in Longboat Key

Less expensive
More expensive
Next month
January
March
$403
Month
Price
January
$323
February
$403
March
$535
April
$454
May
$430
June
$488
July
$472
August
$408
September
$385
October
$370
November
$395
December
$434
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 $322 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.

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 18 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 St. Armands Circle 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.