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Longboat Key Holiday Rentals

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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, (140 reviews)
"We loved it and recommend it and definitely plan another. Locals only lol."
United States
Kenneth
The price is AU$473
includes taxes & fees
18 Oct - 19 Oct
Oceanfront Oasis – Longboat Key 226 by RVA

2. Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (86 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
Relax at Gulf – Silver Sands Resort #232, Longboat

3. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful property. Will definitely stay again."
United States
Tami T.
The price is AU$655
includes taxes & fees
17 Oct - 18 Oct
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

4. 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)
"We really enjoyed our stay. The beach is so stunning! We loved being right on a private beach, waking up and walking right onto it was incredible. They do provide chairs and umbrella but i highly recommend bringing your own. We will definitely stay here again!"
United States
lynn m.
Affordable Beach Studio – Silver Sands #257A by RVA

5. Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (108 reviews)
"It was a great location. It had a nice pool area, plenty of beach chairs and beach goodies to use."
United States
Laurie L.
The price is AU$431
includes taxes & fees
20 Oct - 21 Oct
Oceanfront Bliss–Longboat Key Beach 106 by RVA

6. Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (84 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 AU$440
includes taxes & fees
18 Oct - 19 Oct
Beachfront Studio – Cabana #5B by RVA

7. Renovated Beach Paradise. Ground Floor unit 64

Renovated Beach Paradise. Ground Floor unit 64
Longboat Key
9.8 out of 10, Exceptional, (73 reviews)
"Great place, close to the beach. Will visit again."
United States
Jason W.
Renovated Beach Paradise. Ground Floor unit 64

8. 1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (99 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is AU$534
includes taxes & fees
29 Oct - 30 Oct
1BR Beach Getaway – Silver Sands #254 by RVA

9. Silver Sands Serenity – Unit 234 by RVA

Silver Sands Serenity – Unit 234 by RVA
Longboat Key
9.4 out of 10, Exceptional, (35 reviews)
" Great location, office staff are very pleasant, room was very spacious with everything you need"
United States
GLENNA M.
The price is AU$431
includes taxes & fees
19 Oct - 20 Oct
Silver Sands Serenity – Unit 234 by RVA

10. 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.
The price is AU$583
includes taxes & fees
14 Nov - 15 Nov
Best views of the beach from your balcony Unit 301

11. 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

12. 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, (77 reviews)
"Enjoyed our stay!"
United States
Charles J.
The price is AU$497
includes taxes & fees
24 Oct - 25 Oct
Step from the Beach.Renovated ground Floor unit 63

13. 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 AU$486
includes taxes & fees
25 Oct - 26 Oct
Gulfside Resort – Silver Sands #241A by RVA

14. 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

15. Vitamin Sea: November & December Availability!

Vitamin Sea: November & December Availability!
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 AU$585
includes taxes & fees
4 Nov - 5 Nov
Vitamin Sea: November & December Availability!

16. Coastal Comfort – Beach Castle #26 by RVA

Coastal Comfort – Beach Castle #26 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"Stayed 5 days. Lovely condo, everything we needed was there."
United States
Grace E.
The price is AU$463
includes taxes & fees
18 Oct - 19 Oct
Coastal Comfort – Beach Castle #26 by RVA

17. 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 AU$500
includes taxes & fees
19 Oct - 20 Oct
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

18. Oceanfront 1BR – Silver Sands #257 by RVA

Oceanfront 1BR – Silver Sands #257 by RVA
Longboat Key
8.8 out of 10, Excellent, (53 reviews)
"We loved this unit at Silver Sands and will book again. The only complaint we had was that there was a need for new pillows."
United States
Kinsley C.
Oceanfront 1BR – Silver Sands #257 by RVA

19. 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, (44 reviews)
"Beach was perfect!"
United States
Carmela D.
The price is AU$487
includes taxes & fees
15 Oct - 16 Oct
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

20. 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, (89 reviews)
"Great location and great views!"
United States
Mark H.
The price is AU$531
includes taxes & fees
18 Oct - 19 Oct
The Beach on Longboat Key #227 Resort 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$473 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?

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.