A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Search Holiday Rentals in Longboat Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Longboat Key holiday rentals

1. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (141 reviews)
"The ocean view was great. The room was very clean and we enjoyed the stay."
United States
Sherri G.
The price is £267
includes taxes & fees
19 Nov - 20 Nov
Oceanfront Oasis – Longboat Key 226 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, (86 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: Very nice and quiet place to take a chill vacation"
United States
Stacey K.
The price is £214
includes taxes & fees
5 Nov - 6 Nov
Affordable Beach Studio – Silver Sands #257A by RVA

3. 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, (94 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.
Best views of the beach from your balcony Unit 301

4. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (104 reviews)
"Close to beach and cozy"
United States
Peter
The price is £325
includes taxes & fees
5 Nov - 6 Nov
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

5. Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (90 reviews)
"So homey and comfy! Everything was clean and put together, kitchen had everything I needed for the stay. Umbrellas/floaties/etc were a bonus I wasn’t expecting! Absolutely will come back! Already planning the next one!"
United States
Daniela L.
Silver Sands 1BR – Gulfside Comfort #255 by RVA

6. New Opening: Sunday - Friday!

New Opening: Sunday - Friday!
Longboat Key
10.0 out of 10, Exceptional, (101 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 £271
includes taxes & fees
4 Nov - 5 Nov
New Opening: Sunday - Friday!

7. 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 £248
includes taxes & fees
24 Nov - 25 Nov
Gulfside Resort – Silver Sands #241A by RVA

8. 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
Starfish Studio Silver Sands #247A – Studio/1BA Resort in LBK

9. The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA
Longboat Key
9.2 out of 10, Wonderful, (92 reviews)
"Great location and great views!"
United States
Mark H.
The Beach on Longboat Key #227 Resort by RVA

10. Silver Sands #245A Resort by RVA

Silver Sands #245A Resort by RVA
Longboat Key
8.6 out of 10, Excellent, (64 reviews)
"Location and facilities wer excellent. "
United States
donald m.
Silver Sands #245A Resort by RVA

11. Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Longboat Key
8.2 out of 10, Very good, (25 reviews)
"Great little place to enjoy the beach"
United States
Victoria F.
The price is £245
includes taxes & fees
17 Nov - 18 Nov
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

12. Take a peek at awesome reviews 50 feet from the sand

Take a peek at awesome reviews 50 feet from the sand
Longboat Key
10.0 out of 10, Exceptional, (154 reviews)
"My family and I had a great stay at the property. The proximity to the beach was great for our family and allowed for easy breaks during the day as it was only a minute walk to the beach. Easy drives to Sarasota and Anna Maria Island made for fun day trips with little work to get there. Would recommend for those wanting a relaxing stay with easy beach access and desiring to be outside of the highly tourist traffic. Thanks for a great stay."
United States
Jason C.
The price is £441
includes taxes & fees
10 Nov - 11 Nov
Take a peek at awesome reviews 50 feet from the sand

13. Direct Oceanview on LBK: Open Nov 9th & 10th!

Direct Oceanview on LBK: Open Nov 9th & 10th!
Longboat Key
10.0 out of 10, Exceptional, (138 reviews)
"the absolute best views and beyond better hosts"
United States
Ivan
The price is £265
includes taxes & fees
10 Nov - 11 Nov
Direct Oceanview on LBK: Open Nov 9th & 10th!

14. Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (85 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
The price is £229
includes taxes & fees
4 Nov - 5 Nov
Drift & Dune – Longboat Beachfront #101 RVA

15. Gulf Views – Silver Sands #250, Longboat Key by RVA

Gulf Views – Silver Sands #250, Longboat Key by RVA
Longboat Key
8.8 out of 10, Excellent, (85 reviews)
"The host staff were very helpful."
United States
Ann S.
The price is £330
includes taxes & fees
13 Nov - 14 Nov
Gulf Views – Silver Sands #250, Longboat Key by RVA

16. 1BD/1BA Silver Sands Gulf Front w/Garden View

1BD/1BA Silver Sands Gulf Front w/Garden View
Longboat Key
The price is £269
includes taxes & fees
6 Nov - 7 Nov
1BD/1BA Silver Sands Gulf Front w/Garden View

17. 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, (79 reviews)
"Enjoyed our stay!"
United States
Charles J.
The price is £278
includes taxes & fees
22 Nov - 23 Nov
Step from the Beach.Renovated ground Floor unit 63

18. Coastal Comfort – Silver Sands Resort #233 by RVA

Coastal Comfort – Silver Sands Resort #233 by RVA
Longboat Key
8.8 out of 10, Excellent, (37 reviews)
"3rd time here already booked another trip. So easy! Love it here!"
United States
Emily
The price is £249
includes taxes & fees
18 Nov - 19 Nov
Coastal Comfort – Silver Sands Resort #233 by RVA

19. Beachfront Bliss on Longboat Key- Steps to the sand

Beachfront Bliss on Longboat Key- Steps to the sand
Longboat Key
8.6 out of 10, Excellent, (24 reviews)
"It was a good place it was smaller than I thought but it was perfect for 2 people!"
United States
Pacey D.
The price is £296
includes taxes & fees
5 Nov - 6 Nov
Beachfront Bliss on Longboat Key- Steps to the sand

20. Sunny Daze on LBK: Open Nov 12th & 13th!

Sunny Daze on LBK: Open Nov 12th & 13th!
Longboat Key
9.8 out of 10, Exceptional, (20 reviews)
"Amazing, great host, loved it ."
United States
Reuben T.
The price is £258
includes taxes & fees
12 Nov - 13 Nov
Sunny Daze on LBK: Open Nov 12th & 13th!
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 £245 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. 

Explore a world of travel with Expedia

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?

Tropical Villas of Venice Beach: This holiday home rental outside of Longboat Key is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Longboat Key?

Choose from 17 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. 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.