Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

9.2 out of 10, Wonderful, (93 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: Will stay here again"
United States
Chrissy C.
The price is NZ$1,019
includes taxes & fees
29 Mar - 30 Mar
1BR Beach Getaway – Silver Sands #254 by RVA
8.8 out of 10, Excellent, (74 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: The condo was clean and had all that we needed for our two night stay. Loved it will be back again... just a little walk to the beach and some he pool was very nice as well."
United States
Nancy C.
Newly Renovated 1BR – Cabana Beach #5 RVA
8.6 out of 10, Excellent, (62 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
The price is NZ$605
includes taxes & fees
11 Mar - 12 Mar
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
9.0 out of 10, Wonderful, (37 reviews)
"Great stay and very friendly staff and host."
United States
Ida A.
The price is NZ$904
includes taxes & fees
13 Mar - 14 Mar
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
7.8 out of 10, Good, (9 reviews)
"Great locale right on the beach "
United States
Carole
The price is NZ$803
includes taxes & fees
30 Mar - 31 Mar
Beachfront Bliss on Longboat Key- Steps to the sand
8.8 out of 10, Excellent, (24 reviews)
"Great location. We loved that it was an easy drive to lots of parks an other attractions. Great beach walks."
United States
Deb W.
The price is NZ$736
includes taxes & fees
11 Mar - 12 Mar
1BR Beach Oasis – Silver Sands #258, Longboat Key by RVA
8.8 out of 10, Excellent, (92 reviews)
"Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. "
United States
Jessie
The price is NZ$666
includes taxes & fees
16 Mar - 17 Mar
Oceanfront Bliss–Longboat Key Beach 106 by RVA
9.2 out of 10, Wonderful, (74 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: Silver Sands is a marvelous, peaceful retreat located in Longboat Key. We have vacationed here twice with our young granddaughter - and will return. The resort is well cared for and we have met lovely other guests staying there."
United States
Joan-Marie E.
Poolside Peace – Silver Sands Resort #242 by RVA
8.4 out of 10, Very good, (18 reviews)
"Perfect view, super clean, convenient, was the perfect size for me and my husband. We stayed for our 10 year anniversary and everything was perfect. "
United States
HALEY B.
The price is NZ$1,489
includes taxes & fees
8 Apr - 9 Apr
Updated Beachfront Condo at Prestigious Long Boat Key Resort
10.0 out of 10, Exceptional, (58 reviews)
"Amazing family vacation and loved the location!"
United States
Kaitlin M.
The price is NZ$1,041
includes taxes & fees
21 Mar - 22 Mar
Coastal Comfort - Beach Castle #23 by RVA
9.8 out of 10, Exceptional, (76 reviews)
"Very clean "
United States
Lana
The price is NZ$913
includes taxes & fees
27 Mar - 28 Mar
2BR Gulfside Paradise – Longboat Key by RVA
9.2 out of 10, Wonderful, (75 reviews)
"Was good. Decent place to work remotely. Open to better rate in the future to stay for a month."
United States
Dan S.
The price is NZ$782
includes taxes & fees
20 Mar - 21 Mar
Relax at Gulf – Silver Sands Resort #232, Longboat
9.6 out of 10, Exceptional, (75 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is NZ$707
includes taxes & fees
20 Mar - 21 Mar
Affordable Beach Studio – Silver Sands #257A by RVA
9.8 out of 10, Exceptional, (63 reviews)
"The condo was very clean and the beach was very close."
United States
Rick C.
The price is NZ$670
includes taxes & fees
29 Mar - 30 Mar
Renovated Beach Paradise. Ground Floor unit 64
10.0 out of 10, Exceptional, (84 reviews)
"Beautiful location and the beach is amazing "
United States
Heather A.
The price is NZ$828
includes taxes & fees
6 Apr - 7 Apr
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Apartment in Longboat Key

Silver Sands #245A Resort by RVA
8.6 out of 10, Excellent, (61 reviews)
"They are still recovering a bit from the storms past but longboat is a great local get away and this little place was very quiet and nice."
United States
Kimberly P.
The price is NZ$716
includes taxes & fees
19 Mar - 20 Mar
Silver Sands #245A Resort by RVA
8.4 out of 10, Very good, (47 reviews)
"We enjoyed this fun spot with private beach, pool, and more!"
United States
Willow C.
The price is NZ$830
includes taxes & fees
27 Mar - 28 Mar
Gulfside Resort – Silver Sands #241A by RVA
10.0 out of 10, Exceptional, (88 reviews)
"The perfect beach cottage for our wedding anniversary. We had everything we needed including beautiful weather ."
United States
Julie Q.
The price is NZ$858
includes taxes & fees
18 Mar - 19 Mar
Vitamin Sea Escape: Open Wed, March 18th!
9.0 out of 10, Wonderful, (28 reviews)
"This place has an old Florida vibe. It was a great place to enjoy a weekend with friends. The condo had everything we needed and easy walk to the beach. We saw some beautiful sunsets."
United States
Janet S.
The price is NZ$987
includes taxes & fees
19 Mar - 20 Mar
Silver Sands #245S Resort by RVA
9.4 out of 10, Exceptional, (11 reviews)
"Loved the tennis courts, pool, bikes, views from both sides. Also really appreciated all the beach and game equipment that was there for us to use."
United States
dan b.
The price is NZ$1,261
includes taxes & fees
27 Mar - 28 Mar
Find Your Sunshine Sanctuary on Longboat Key
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$650 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 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 St. Armands Circle 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.