Longboat Key Holiday Rentals

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Holiday Rentals in Longboat Key

Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (300)
"My 4 night stay was beautiful and relaxing for the most part. Although, for being one of the few people residing there for a short vacation, I would've preferred that they hadn't put a rather noisey family right above me. It was startling and intrusive at times. "
Sea Club I Beach Resort
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (137)
"Cute little cottage with 2br, 1ba. Very clean, close to the beach. Lots of supplies for the beach. Could use softer towels in bathroom and perhaps some instructions on the shower as it was quite hot on any setting. Prior communication was slow but once there was pretty attentive. "
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Breathtaking Beach Front Property Ground Floor Condo
On the beach

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (129)
"Thank You, Matt for the perfect condo to enjoy our vacation. The condo was clean and had everything we needed to make our stay perfect. The grounds,beach and pool were perfect also. We would definitely rent again 😀🌴☀️ Also enjoyed our daily visits from George 🕊"
Breathtaking Beach Front Property Ground Floor Condo
THE BEACH, condo #107, PRIVATE BEACH Open 1/1/2025
Sun-loungers, beach towels

THE BEACH, condo #107, PRIVATE BEACH Open 1/1/2025

9.8 out of 10, Exceptional, (60)
"Very nice "
The price is HK$1,750
HK$3,262 total
includes taxes & fees
11 Jan - 12 Jan 2025
THE BEACH, condo #107, PRIVATE BEACH Open 1/1/2025
Direct Beachfront Gulf with Amazing Views
On the beach, sun-loungers, beach towels

Direct Beachfront Gulf with Amazing Views

9.8 out of 10, Exceptional, (89)
"What a fantastic spot. The beach was terrific… the condo had every amenity we needed…. The pool was lovely. Dolphins and manatees in the water… close to restaurants and shopping. Beautiful sunsets and storm watching. We are so sad to be leaving because we had such an amazing vacation. I can’t think of a single thing we would have done differently. Thank you!!!"
Direct Beachfront Gulf with Amazing Views
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (13)
"The property looked exactly like the photos. It was clean, in a very quiet neighbourhood close to the beach & some good restaurants. Beds were comfortable. Kitchen could have done with more stock (there were 8 of us staying & not enough crockery or cutlery) but wasn’t a huge issue. We loved the location & how quiet it was, so would definitely stay again."
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Panoramic beach View and amazing Sunset.
Property grounds

Panoramic beach View and amazing Sunset.

9.8 out of 10, Exceptional, (95)
"Beautiful unit!"
The price is HK$1,516
HK$3,347 total
includes taxes & fees
2 Jan - 3 Jan 2025
Panoramic beach View and amazing Sunset.
5 floor penthouse 60 feet from the sand Dec15-24open beach open
Property grounds

5 floor penthouse 60 feet from the sand Dec15-24open beach open

9.8 out of 10, Exceptional, (182)
"The condo was perfect! Everything we needed at our fingertips. and the view was amazing! Right on the ocean, the beach was clean & quiet. Close to St Armand’s Circle and many island restaurants to choose from. Check in & communication before, during & after our stay was great. We would definitely stay here again!"
The price is HK$2,247
HK$4,405 total
includes taxes & fees
23 Dec - 24 Dec
5 floor penthouse 60 feet from the sand Dec15-24open beach open
The Beach on Longboat Key #220 Resort by RVA
On the beach

The Beach on Longboat Key #220 Resort by RVA

8.0 out of 10, Very good, (42)
"We enjoyed our stay! We had all the necessaries for a few days at the beach. It’s a great price point if you’re just looking for a little rest on the beach. There are local restaurants just a few miles down the road. The only think I would suggest is that the property provide a broom for the room. You’re at the beach so of course, there is going to be sand. We are planning on coming back. "
The Beach on Longboat Key #220 Resort by RVA
Beach view. Year-round Balcony Sunsets. Just renovated.
Property grounds

Beach view. Year-round Balcony Sunsets. Just renovated.

9.8 out of 10, Exceptional, (73)
"Beautiful view.. home was clean and the front staff was amazing. "
The price is HK$1,361
HK$3,141 total
includes taxes & fees
5 Jan - 6 Jan 2025
Beach view. Year-round Balcony Sunsets. Just renovated.
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
On the beach, sun-loungers, beach towels

Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.

9.4 out of 10, Exceptional, (44)
"This hotel is nice "
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,
Exterior

Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,

9.8 out of 10, Exceptional, (229)
"This property is so special. Right on the beach and with only 4 units in the building it feels like your own private beach. The unit itself is large, clean and nicely decorated. I look forward to staying here again. "
Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,
The Beach on Longboat Key #104 Resort by RVA
On the beach

The Beach on Longboat Key #104 Resort by RVA

9.0 out of 10, Wonderful, (93)
"Very pleasant stay."
The Beach on Longboat Key #104 Resort by RVA
Silver Sands #236 Resort by RVA
On the beach, beach umbrellas

Silver Sands #236 Resort by RVA

9.2 out of 10, Wonderful, (62)
"Fantastic!"
The price is HK$980
HK$2,267 total
includes taxes & fees
23 Dec - 24 Dec
Silver Sands #236 Resort by RVA
Turtle Crawl Inn
Terrace/patio

Turtle Crawl Inn

3.0 star property
8.6 out of 10, Excellent, (90)
"Everything was clean. Office workers were friendly and had no problem with my brother’s family coming to visit for the day. "
Turtle Crawl Inn
Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.
On the beach, sun-loungers, beach towels

Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.

9.8 out of 10, Exceptional, (53)
"Great location! You won’t be disappointed. The beach is just steps away. Communication with the owner was the best! We needed more blankets(my kids don’t share). Owner answered on the first call and had it handled in minutes. Condo was super clean, adorable and had everything we needed. Thank you for allowing us to stay."
The price is HK$1,050
HK$2,762 total
includes taxes & fees
29 Dec - 30 Dec
Beach Front No Crossing Needed One Bedroom Condo. Fully Renovated. Ground Floor.
2BR Walk to the Beach Across the Street- Bay Views!
Beach

2BR Walk to the Beach Across the Street- Bay Views!

9.8 out of 10, Exceptional, (8)
"Laid-back and a ton of space with beautiful view. Staff was incredibly helpful."
2BR Walk to the Beach Across the Street- Bay Views!
Silver Sands #237 Resort by RVA
On the beach, beach umbrellas

Silver Sands #237 Resort by RVA

9.0 out of 10, Wonderful, (38)
"Steps to the beach and included towels, beach chairs and umbrellas. Staff was extremely nice and we enjoyed the joke of the day while checking in!"
The price is HK$1,213
HK$2,575 total
includes taxes & fees
30 Dec - 31 Dec
Silver Sands #237 Resort by RVA
Beach View Condo- Quiet & Secluded with Private Beach
On the beach, sun-loungers, beach towels

Beach View Condo- Quiet & Secluded with Private Beach

10.0 out of 10, Exceptional, (21)
"10/10! We stayed at this property Nov 21-26 (my mom, 2 boys age 5 and 7, and myself). The property was easy to get to (25 min drive from Sarasota-Bradenton), check-in was effortless (host sent a code), and the property was very clean and quiet. When you see how close the beach is in the pictures, that truly is how close it is! The chairs on the beach were super convenient. The seller was an excellent communicator! She kept in touch with us after the hurricane and was upfront about issues caused...
Beach View Condo- Quiet & Secluded with Private Beach
Updated Beachfront Condo at Prestigious Long Boat Key Resort
A heated pool

Updated Beachfront Condo at Prestigious Long Boat Key Resort

8.6 out of 10, Excellent, (11)
"Secluded property in a gated community. Beach and ocean views tremendous. Loved sitting on the balcony (which is twice as long as the picture) and drinking coffee while relaxing in the morning."
The price is HK$3,880
HK$7,762 total
includes taxes & fees
23 Dec - 24 Dec
Updated Beachfront Condo at Prestigious Long Boat Key Resort
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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Other types of properties in Longboat Key you may be interested in

Zota Beach Resort
Breakfast, lunch and dinner served

Zota Beach Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful beach right outside our balcony!"
The price is HK$2,325
HK$2,976 total
includes taxes & fees
5 Jan - 6 Jan 2025
Zota Beach Resort
The St. Regis Longboat Key Resort
Exterior

The St. Regis Longboat Key Resort

5.0 star property
10.0 out of 10, Exceptional, (10)
"Loved it"
The price is HK$6,928
HK$8,312 total
includes taxes & fees
6 Jan - 7 Jan 2025
The St. Regis Longboat Key Resort
The Resort at Longboat Key Club
Exterior

The Resort at Longboat Key Club

4.0 star property
8.8 out of 10, Excellent, (638)
"Staff excellent. Elevators need work. Rooms very nice. Beach excellent "
The price is HK$4,191
HK$5,087 total
includes taxes & fees
2 Jan - 3 Jan 2025
The Resort at Longboat Key Club
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.

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?

SEPT OCT NOV DISCOUNTS! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!: This holiday home rental outside of Longboat Key offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Longboat Key?

Choose from 178 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. 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.