Longboat Key Holiday Rentals

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Holiday Rentals in Longboat Key

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (327)
"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

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

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

8.8 out of 10, Excellent, (27)
"Amazing property. Comfortable beds, great view/location, 1 mile from Publix. Absolutely perfect!"
The price is NZ$805
includes taxes & fees
5 Oct - 6 Oct
Beach front 2 bed-2 bath private balcony, modern with Gulf front views

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

10.0 out of 10, Exceptional, (77)
"The area was perfect as well as the condo and the host! The property was in a beautiful area, and the condo and property is very clean and well maintained. Would definitely recommend!"
The price is NZ$747
includes taxes & fees
12 Oct - 13 Oct
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

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

10.0 out of 10, Exceptional, (130)
"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 NZ$859
includes taxes & fees
30 Sept - 1 Oct
Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.

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 NZ$751
includes taxes & fees
30 Sept - 1 Oct
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

9.8 out of 10, Exceptional, (88)
"Very nice townhouse with excellent amenities. Located near great restaurants and beaches. Would definitely stay there again."
Country Club Long Boat Key Beach Villa 2B 3BA Pool No Hurricane Damage

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 NZ$724
includes taxes & fees
1 Oct - 2 Oct
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

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

10.0 out of 10, Exceptional, (196)
"Very relaxing "
Flash sale Sept 2-4/ 7-13, 5-floor penthouse 60 feet from water, 150+ reviews

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

Cedars East Townhome on beautiful Longboat Key

9.6 out of 10, Exceptional, (21)
"One of the best places we've stayed using VRBO. Would definitely return and recommend to others."
Cedars East Townhome on beautiful Longboat Key

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (147)
"This property was perfect for our sister trip! Location, property condition and communication was excellent! "
Breathtaking Beach Front Property Ground Floor Condo

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

Right on the beach.Renovated ground Floor unit 63.

9.4 out of 10, Exceptional, (54)
"We thoroughly enjoyed our stay-perfect location, great accommodations, and wonderful staff!"
The price is NZ$551
includes taxes & fees
30 Sept - 1 Oct
Right on the beach.Renovated ground Floor unit 63.

Sunset and Beach view unit 402

9.8 out of 10, Exceptional, (8)
"So quiet, I loved it"
The price is NZ$640
includes taxes & fees
1 Oct - 2 Oct
Sunset and Beach view unit 402

Best views of the beach from your balcony Unit 301

9.8 out of 10, Exceptional, (85)
"It was so great loved everything in the home"
The price is NZ$661
includes taxes & fees
2 Oct - 3 Oct
Best views of the beach from your balcony Unit 301

Unforgettable Oceanfront Oasis-The Beach on Longboat Key #226 by RVA

9.2 out of 10, Wonderful, (119)
"Location was great! Studio apartment was good. Was very nice to have a balcony to sit and enjoy a cup of coffee in the morning and watch and listen to the ocean. Just a few steps onto the beach/ocean. Perfect Spot to relax! Will definitely return again. "
The price is NZ$578
includes taxes & fees
26 Oct - 27 Oct
Unforgettable Oceanfront Oasis-The Beach on Longboat Key #226 by RVA

Spacious 3 Bedroom with Deck Gulfside Condo - Silver Sands #238 Resort by RVA

9.6 out of 10, Exceptional, (58)
"this place is amazing, we had a wonderful time. we will be back again"
The price is NZ$1,058
includes taxes & fees
2 Oct - 3 Oct
Spacious 3 Bedroom with Deck Gulfside Condo - Silver Sands #238 Resort by RVA

Client texted view crazy

10.0 out of 10, Exceptional, (91)
"Longboat Key is just beautiful and quiet. This condo has excellent access to the beach. We enjoyed our stay. "
Client texted view crazy

Charming Longboat Key Bungalow with beach access minutes away…

2.0 star property
9.4 out of 10, Exceptional, (12)
"Very cute place. It was in a great spot for easy access to the beach and restaurants. "
The price is NZ$686
includes taxes & fees
6 Oct - 7 Oct
Charming Longboat Key Bungalow with beach access minutes away…
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 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$551 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?

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 170 Expedia holiday rentals in Longboat Key for a memorable holiday.

What can I see and do in Longboat Key?

Jewfish Key and Quick Point Nature Reserve 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.