Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

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, (88 reviews)
"It was so great loved everything in the home"
United States
TERRY C.
The price is NZ$705
includes taxes & fees
23 Jan - 24 Jan
Best views of the beach from your balcony Unit 301

Sunset and Beach view unit 402

Sunset and Beach view unit 402
Longboat Key
9.8 out of 10, Exceptional, (15 reviews)
"Accommodation were outstanding with beautiful views of the gulf!"
United States
Mike C.
The price is NZ$663
includes taxes & fees
30 Jan - 31 Jan
Sunset and Beach view unit 402

Silver Sands Serenity – Unit 234 by RVA

Silver Sands Serenity – Unit 234 by RVA
Longboat Key
9.4 out of 10, Exceptional, (30 reviews)
"Love this place and staff. Will book again. Everything is so easy!"
United States
Emily
The price is NZ$593
includes taxes & fees
29 Jan - 30 Jan
Silver Sands Serenity – Unit 234 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.
Beachfront Studio – Cabana #5B 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, (257 reviews)
"Loved this place. Would stay again. Very clean and right by the beach. Worth staying and highly reccomend. Hosts were very communicative as well. "
United States
Brenda V.
Luxury Beach Condo - Ocean View w/ Fireplace. 2br/2ba. Full Kitchen

Newly Renovated 1BR – Cabana Beach #5 RVA

Newly Renovated 1BR – Cabana Beach #5 RVA
Longboat Key
8.8 out of 10, Excellent, (73 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

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (88 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
Oceanfront Bliss–Longboat Key Beach 106 by RVA

Ground Floor Oceanview: Open SU & MO, $225/nt + Fees!

Ground Floor Oceanview: Open SU & MO, $225/nt + Fees!
Longboat Key
9.6 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay, the condo was very well equipped and the host was absolutely fantastic! "
United States
Emily L.
The price is NZ$726
includes taxes & fees
30 Jan - 31 Jan
Ground Floor Oceanview: Open SU & MO, $225/nt + Fees!

Cozy Beach Studio – Silver Sands #251A by RVA

Cozy Beach Studio – Silver Sands #251A by RVA
Longboat Key
8.6 out of 10, Excellent, (49 reviews)
"all good , an ice machine would have been nice"
United States
Randy W.
Cozy Beach Studio – Silver Sands #251A by RVA

Silver Sands 256 on LBK!

Silver Sands 256 on LBK!
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.
The price is NZ$721
includes taxes & fees
30 Jan - 31 Jan
Silver Sands 256 on LBK!

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.
Bright Beach Studio – Silver Sands #255A by RVA

Relaxing 2BR Retreat-Silver Sands Resort

Relaxing 2BR Retreat-Silver Sands Resort
Longboat Key
9.6 out of 10, Exceptional, (25 reviews)
"Great location! Speedy check-in and check-out. Was perfect for our party of 3."
United States
Anonymous traveller
Relaxing 2BR Retreat-Silver Sands Resort

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (90 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.
1BR Beach Getaway – Silver Sands #254 by RVA

Direct Oceanview on LBK!

Direct Oceanview on LBK!
Longboat Key
10.0 out of 10, Exceptional, (118 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 NZ$720
includes taxes & fees
27 Jan - 28 Jan
Direct Oceanview on LBK!

Coastal Comfort – Beach Castle #26 by RVA

Coastal Comfort – Beach Castle #26 by RVA
Longboat Key
9.4 out of 10, Exceptional, (40 reviews)
"We had a great time and the place was beautiful "
United States
Michelle B.
The price is NZ$567
includes taxes & fees
30 Jan - 31 Jan
Coastal Comfort – Beach Castle #26 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.
Sunset and beach view from your balcony Unit 403

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.
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
2BR Gulfside Paradise – Longboat Key by RVA

Right on the beach.Renovated ground Floor unit 63.

Right on the beach.Renovated ground Floor unit 63.
Longboat Key
9.6 out of 10, Exceptional, (57 reviews)
"Excellent, clean, and friendly"
United States
John G.
The price is NZ$588
includes taxes & fees
1 Feb - 2 Feb
Right on the beach.Renovated ground Floor unit 63.

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.
The price is NZ$671
includes taxes & fees
29 Jan - 30 Jan
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

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$535 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 18 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. 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.