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Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

1. 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 traveller
The price is NZ$655
includes taxes & fees
13 Sept - 14 Sept
Silver Sands 1BR – Gulfside Comfort #255 by RVA

2. 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.
The price is NZ$546
includes taxes & fees
15 Sept - 16 Sept
Affordable Beach Studio – Silver Sands #257A by RVA

3. 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
The price is NZ$576
includes taxes & fees
13 Sept - 14 Sept
Relax at Gulf – Silver Sands Resort #232, Longboat

4. 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
The price is NZ$649
includes taxes & fees
21 Sept - 22 Sept
Seashells by the Seashore: Open Sept 21st & 22nd!

5. 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

6. 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.
The price is NZ$581
includes taxes & fees
13 Sept - 14 Sept
Gulfside Resort – Silver Sands #241A by RVA

7. 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
The price is NZ$564
includes taxes & fees
13 Sept - 14 Sept
Seaside Escape – Beach Castle #24 by RVA

8. 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.
The price is NZ$588
includes taxes & fees
13 Sept - 14 Sept
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

9. 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
The price is NZ$633
includes taxes & fees
11 Sept - 12 Sept
1BR Beach Getaway – Silver Sands #254 by RVA

10. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (99 reviews)
"Beautiful property. Will definitely stay again."
United States
Tami T.
The price is NZ$670
includes taxes & fees
15 Sept - 16 Sept
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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.
The price is NZ$566
includes taxes & fees
13 Sept - 14 Sept
Silver Sands #245A Resort by RVA

12. 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.
The price is NZ$525
includes taxes & fees
11 Oct - 12 Oct
Beachfront Studio – Cabana #5B by RVA

13. 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
The price is NZ$564
includes taxes & fees
13 Sept - 14 Sept
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

14. Beach Escape – Silver Sands Resort #246 by RVA

Beach Escape – Silver Sands Resort #246 by RVA
Longboat Key
9.0 out of 10, Wonderful, (68 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: A wonderful place to rest, restore and enjoy this beautiful island and beach"
United States
A guest from Crawfordsville, IN
Beach Escape – Silver Sands Resort #246 by RVA

15. 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.
The price is NZ$572
includes taxes & fees
13 Sept - 14 Sept
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

16. 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.
The price is NZ$919
includes taxes & fees
13 Sept - 14 Sept
Gulf Getaway – Beach Castle #12 by RVA

17. 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
The price is NZ$556
includes taxes & fees
13 Sept - 14 Sept
Coastal Comfort – Silver Sands Resort #233 by RVA

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)
"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.
The price is NZ$696
includes taxes & fees
17 Sept - 18 Sept
Best views of the beach from your balcony Unit 301

19. 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, (74 reviews)
"Enjoyed our stay!"
United States
Charles J.
Step from the Beach.Renovated ground Floor unit 63

20. 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 traveller
The price is NZ$690
includes taxes & fees
10 Oct - 11 Oct
Sunset and beach view from your balcony Unit 403
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

Find out more about Longboat Key

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Longboat Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Longboat Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Longboat Key. Seeing all the best attractions is bound to make you fall in love with Longboat Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Longboat Key short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Longboat Key?

Yes, there are holiday rentals close to the most popular sights in Longboat Key, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Longboat Key has to offer?

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

How many holiday rentals are there in Longboat Key?

Choose from 19 Expedia holiday rentals in Longboat Key for a memorable holiday.

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 holiday rentals like in Longboat Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longboat Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.