Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
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 AU$938
includes taxes & fees
29 Mar - 30 Mar
1BR Beach Getaway – Silver Sands #254 by RVA

Updated Beachfront Condo at Prestigious Long Boat Key Resort

Updated Beachfront Condo at Prestigious Long Boat Key Resort
Longboat Key
8.6 out of 10, Excellent, (17 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 AU$1,429
includes taxes & fees
3 Mar - 4 Mar
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Longboat Key
9.0 out of 10, Wonderful, (36 reviews)
"Great stay and very friendly staff and host."
United States
Ida A.
The price is AU$746
includes taxes & fees
13 Mar - 14 Mar
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Sun- Kissed Memories!

Sun- Kissed Memories!
Longboat Key
10.0 out of 10, Exceptional, (119 reviews)
"Great hostess, very thoughtful and kind. She thought of everything, we didn’t have to leave the premises. The location is unbelievable and the condo is gorgeous. We will definitely stay again!!"
United States
Amy K
The price is AU$717
includes taxes & fees
26 Mar - 27 Mar
Sun- Kissed Memories!

Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
7.8 out of 10, Good, (7 reviews)
"Great locale right on the beach "
United States
Carole
The price is AU$507
includes taxes & fees
11 Mar - 12 Mar
Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (74 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
The price is AU$440
includes taxes & fees
3 Mar - 4 Mar
Beachfront Studio – Cabana #5B by RVA

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
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.
The price is AU$509
includes taxes & fees
10 Mar - 11 Mar
Newly Renovated 1BR – Cabana Beach #5 RVA

Direct Beach Access – Silver Sands #249 by RVA

Direct Beach Access – Silver Sands #249 by RVA
Longboat Key
9.2 out of 10, Wonderful, (58 reviews)
"Perfect location "
United States
Rachel H.
The price is AU$936
includes taxes & fees
8 Mar - 9 Mar
Direct Beach Access – Silver Sands #249 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, (31 reviews)
"Extremely convenient access to beach, Large pool, putting green, and pool toys made our stay very fun. "
United States
Maria
The price is AU$827
includes taxes & fees
22 Mar - 23 Mar
Steps to Beach – Silver Sands 2BR Condo #243S by 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
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.
The price is AU$915
includes taxes & fees
22 Mar - 23 Mar
Coastal Comfort - Beach Castle #23 by RVA

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (74 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 AU$539
includes taxes & fees
7 Mar - 8 Mar
Relax at Gulf – Silver Sands Resort #232, Longboat

Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
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 AU$553
includes taxes & fees
29 Mar - 30 Mar
Renovated Beach Paradise. Ground Floor unit 64

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, (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 AU$489
includes taxes & fees
4 Mar - 5 Mar
Ground Floor, Steps to Sand – Silver Sands #243A 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, (47 reviews)
"We enjoyed this fun spot with private beach, pool, and more!"
United States
Willow C.
The price is AU$656
includes taxes & fees
27 Mar - 28 Mar
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, (65 reviews)
"Perfect location and well-maintained unit - highly recommend!"
United States
Philip K.
The price is AU$641
includes taxes & fees
20 Mar - 21 Mar
Bright Beach Studio – Silver Sands #255A by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
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 AU$526
includes taxes & fees
11 Mar - 12 Mar
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Silver Sands #245S Resort by RVA

Silver Sands #245S Resort by RVA
Longboat Key
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 AU$774
includes taxes & fees
13 Mar - 14 Mar
Silver Sands #245S Resort by RVA

Vitamin Sea Escape!

Vitamin Sea Escape!
Longboat Key
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 AU$624
includes taxes & fees
18 Mar - 19 Mar
Vitamin Sea Escape!

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
Coastal Comfort – Silver Sands Resort #233 by 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

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 favourite 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 depend 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 AU$502 per night. Entering your travel dates in the search wizard might find you 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 16 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.