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Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.4 out of 10, Exceptional, (81 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$579
includes taxes & fees
27 July - 28 July
Relax at Gulf – Silver Sands Resort #232, Longboat

Vitamin Sea!

Vitamin Sea!
Longboat Key
10.0 out of 10, Exceptional, (94 reviews)
"The room has direct beach access, plenty of beach chairs. The water and amenities are beautiful, very comfortable bed and the owner couldn't have been any more pleasant or easier to deal with. We had a great stay. 5 stars."
United States
Chuck B.
The price is NZ$686
includes taxes & fees
27 July - 28 July
Vitamin Sea!

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (88 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: Beautiful beach, would stay again."
United States
Michael M.
The price is NZ$656
includes taxes & fees
25 Aug - 26 Aug
Silver Sands 1BR – Gulfside Comfort #255 by RVA

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (80 reviews)
"Thirty steps to the sand! This unit was perfect for my one-person getaway to the beach. Clean and safe, friendly staff, and great location. I'll be back!"
United States
Susan F.
The price is NZ$549
includes taxes & fees
10 Aug - 11 Aug
Affordable Beach Studio – Silver Sands #257A 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, (115 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$704
includes taxes & fees
9 Aug - 10 Aug
Sunset and beach view from your balcony Unit 403

Gulf Getaway – Beach Castle #12 by RVA

Gulf Getaway – Beach Castle #12 by RVA
Longboat Key
9.6 out of 10, Exceptional, (43 reviews)
"Very nice unit. Comfortable, clean, well equipped. Great location. "
United States
EUGENE O.
The price is NZ$686
includes taxes & fees
27 July - 28 July
Gulf Getaway – Beach Castle #12 by RVA

Steps to Beach – Silver Sands 2BR Condo #243S by RVA

Steps to Beach – Silver Sands 2BR Condo #243S by RVA
Longboat Key
9.2 out of 10, Wonderful, (33 reviews)
"Extremely convenient access to beach, Large pool, putting green, and pool toys made our stay very fun. "
United States
Maria
The price is NZ$899
includes taxes & fees
8 Aug - 9 Aug
Steps to Beach – Silver Sands 2BR Condo #243S by RVA

Coastal Comfort – Beach Castle #26 by RVA

Coastal Comfort – Beach Castle #26 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"Very enjoyable."
United States
Todd K.
The price is NZ$563
includes taxes & fees
27 July - 28 July
Coastal Comfort – Beach Castle #26 by RVA

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (81 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$536
includes taxes & fees
29 July - 30 July
Beachfront Studio – Cabana #5B by RVA

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$634
includes taxes & fees
11 Aug - 12 Aug
1BR Beach Getaway – Silver Sands #254 by RVA

Seaside Escape – Beach Castle #24 by RVA

Seaside Escape – Beach Castle #24 by RVA
Longboat Key
9.2 out of 10, Wonderful, (50 reviews)
"Condo was clean, nicely decorated, comfy king bed and the property was charming and quiet.Appreciated the back deck and view of the bay.Also convenient to many restaurants and the beach.Also loved access to the club down the street."
United States
Jody B.
The price is NZ$546
includes taxes & fees
27 July - 28 July
Seaside Escape – Beach Castle #24 by RVA

Gulfside Resort – Silver Sands #241A by RVA

Gulfside Resort – Silver Sands #241A by RVA
Longboat Key
8.4 out of 10, Very good, (49 reviews)
"Beach is beautiful, location is great. Room was clean. Rhe bed"
United States
Kellie B.
The price is NZ$583
includes taxes & fees
10 Aug - 11 Aug
Gulfside Resort – Silver Sands #241A by RVA

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (69 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: Our experience was fantastic and everything was just as described. The place was clean and close to everything."
United States
Chris C.
The price is NZ$563
includes taxes & fees
27 July - 28 July
Bright Beach Studio – Silver Sands #255A 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, (63 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$559
includes taxes & fees
29 July - 30 July
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

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, (43 reviews)
"Enjoyed our stay"
United States
Susan C.
The price is NZ$599
includes taxes & fees
25 Aug - 26 Aug
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

2BR Gulfside Paradise – Longboat Key by RVA

2BR Gulfside Paradise – Longboat Key by RVA
Longboat Key
9.8 out of 10, Exceptional, (84 reviews)
"Beautiful location- perfect for the whole family."
United States
Dana B.
The price is NZ$874
includes taxes & fees
20 Aug - 21 Aug
2BR Gulfside Paradise – Longboat Key by RVA

Gulf Front Escape – Silver Sands #252 by RVA

Gulf Front Escape – Silver Sands #252 by RVA
Longboat Key
9.0 out of 10, Wonderful, (107 reviews)
"Staff was welcoming- place was clean and stay was great"
United States
Joseph S.
The price is NZ$664
includes taxes & fees
30 July - 31 July
Gulf Front Escape – Silver Sands #252 by RVA

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (75 reviews)
"The view and beach access was amazing. Loved our stay. "
United States
Julie F.
The price is NZ$622
includes taxes & fees
29 July - 30 July
Newly Renovated 1BR – Cabana Beach #5 RVA

Coastal Comfort – Silver Sands Resort #233 by RVA

Coastal Comfort – Silver Sands Resort #233 by RVA
Longboat Key
9.0 out of 10, Wonderful, (33 reviews)
"3rd time here already booked another trip. So easy! Love it here!"
United States
Emily
The price is NZ$547
includes taxes & fees
6 Aug - 7 Aug
Coastal Comfort – Silver Sands Resort #233 by RVA

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
Longboat Key
8.0 out of 10, Very good, (9 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$575
includes taxes & fees
25 Aug - 26 Aug
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK
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

Everything you need to know about Longboat Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Longboat Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Longboat Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Longboat Key holiday rentals we have selected for you start as low as NZ$523 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key holiday 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 holiday.

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 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 21 Expedia holiday rentals in Longboat Key for a memorable holiday.

What can I see and do in Longboat Key?

Jewfish Key and Longboat Key Beaches 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 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.