Longboat Key Holiday Rentals

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Holiday Rentals in Longboat Key

Our top choices for Longboat Key holiday rentals

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (324)
"Amazing place, it’s the perfect place for relax and enjoy the beach. I love and I will come back again and again."
Sea Club I Beach Resort

THE BEACH #107 Summer special 210 nite+fees Beachfront Full View

10.0 out of 10, Exceptional, (75)
"Our second time here and it was wonderful again. Annette is very sweet and the place is perfect!"
The price is AU$608
includes taxes & fees
29 Sept - 30 Sept
THE BEACH #107 Summer special 210 nite+fees Beachfront Full View

Longboat Key beach house - 5 min walk to the beaches and top local restaurants

9.4 out of 10, Exceptional, (29)
"What a beautiful propertyNicely decorated. Very convenient with 4 bedrooms all in one floor The peacocks are a nice touch. Access to the beach is very close with parking. The whole area is beautifulHighly recommended "
Longboat Key beach house - 5 min walk to the beaches and top local restaurants

Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

9.4 out of 10, Exceptional, (120)
"We were in town for a wedding and this spot was conveniently located and had great pool and beach access. "
Longboat Key bliss. A perfect Retreat at Cabana Beach Club #9.Also available#8

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

8.8 out of 10, Excellent, (26)
"Great view and nice place for a short stay. "
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.

10.0 out of 10, Exceptional, (129)
"You can not get any closer to the beach than this. The view, the room and our property manager were all amazing. ZERO complaints. Can't wait to go back. "
The price is AU$797
includes taxes & fees
29 Sept - 30 Sept
Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

9.6 out of 10, Exceptional, (82)
"Amazing location!! Was so peaceful and exactly what we needed for a weekend getaway. "
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews

10.0 out of 10, Exceptional, (194)
"Very relaxing "
Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8.8 out of 10, Excellent, (18)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
The price is AU$655
includes taxes & fees
30 Sept - 1 Oct
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Sunset and Beach view unit 402

10.0 out of 10, Exceptional, (5)
"Clean condo. Beautiful view of Gulf"
Sunset and Beach view unit 402

GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

9.8 out of 10, Exceptional, (103)
"This is our 4th year in this condo and we absolutely love it. Such a comfortable space and a perfect location. "
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

8.8 out of 10, Excellent, (11)
"Lovely beach front getaway. Very private and relaxing, far away from the crowds."
The price is AU$635
includes taxes & fees
29 Sept - 30 Sept
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

Beachfront Villa on Serene Gulf of Mexico

9.4 out of 10, Exceptional, (58)
"Everything was great from checking in to checking out. We had some issues with the place but they quickly took care of them. "
Beachfront Villa on Serene Gulf of Mexico

Longboat Bay Club

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
Longboat Bay Club

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (146)
"This property was perfect for our sister trip! Location, property condition and communication was excellent! "
Breathtaking Beach Front Property Ground Floor Condo

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

9.8 out of 10, Exceptional, (154)
"Our stay was perfect! Everything we needed was in the unit and the communication with the owner was great. Can't wait to visit again soon."
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

Hidden Gem | Longboat Key 2BR w/ Beach Access

9.6 out of 10, Exceptional, (26)
"We loved staying on the Key and the place was great. What an awesome condo. We had a great time and the staff was the best. "
Hidden Gem | Longboat Key 2BR w/ Beach Access

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

9.8 out of 10, Exceptional, (9)
"We had a great time at La Playa. The beach is beautiful. The condo is nice, well stocked and quiet. Will definitely stay there again. Maybe next February."
LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

Turtle Shores BEACHFRONT Retreat! Waterfront oasis to completely unwind!

9.8 out of 10, Exceptional, (18)
"Excellent location right on the beach. Wonderful patio"
Turtle Shores BEACHFRONT Retreat! Waterfront oasis to completely unwind!

Breathtaking Direct Gulf Views! Silver Sands Unit 259 - Longboat Key, by RVA

9.0 out of 10, Wonderful, (70)
"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: Family of four, we stayed for 5 days and thoroughly enjoyed our trip we loved the room, and lived how close to the Gulf we were. Great view and screened patio protected is from mosquitos! Perfect! Thanks so much!"
Breathtaking Direct Gulf Views! Silver Sands Unit 259 - Longboat Key, 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

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$608 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 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 170 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 Lido 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.