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, (298)
"Great property! Great front desk people! Beautiful beach!"
Sea Club I Beach Resort
Breathtaking Beach Front Property Ground Floor Condo
On the beach
Breathtaking Beach Front Property Ground Floor Condo
9.6 out of 10, Exceptional, (128)
"Upscale, very well kept condo with all the necessary items for a pleasant vacation. Quality towels and linen. Very clean and tastefully decorated. No clutter. Highly recommend."
Breathtaking Beach Front Property Ground Floor Condo
Waterfront home with private beach, a private pool, and water activities! Moku
On the beach
Waterfront home with private beach, a private pool, and water activities! Moku
10.0 out of 10, Exceptional, (2)
"We had a great stay! It was definitely an experience. It was a peaceful island getaway. If you are able to stay here I recommend it! Any issues we had the AMI team had a quick and efficient response-the only issues we had was our door code didn’t work for all the doors but they responded quickly and got us in in a blink of an eye, and the trash bins outside were almost full but they were out the next day to empty them so no complaints with that! Our only thing was the water in the house is VERY...
Waterfront home with private beach, a private pool, and water activities! Moku
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, (42)
"Wonderful efficiency unit, great location, very clean, all amenities that you can expect. Absolutely perfect for what we expected. "
The price is HK$973
HK$2,459 total
includes taxes & fees
26 Nov - 27 Nov
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
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
Panoramic beach View and amazing Sunset.
Property grounds
Panoramic beach View and amazing Sunset.
9.8 out of 10, Exceptional, (94)
"Beautiful unit!"
The price is HK$1,549
HK$3,431 total
includes taxes & fees
5 Dec - 6 Dec
Panoramic beach View and amazing Sunset.
THE BEACH, condo #107, PRIVATE BEACH
Sun-loungers, beach towels
THE BEACH, condo #107, PRIVATE BEACH
9.8 out of 10, Exceptional, (60)
"Very nice "
THE BEACH, condo #107, PRIVATE BEACH
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
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!"
Silver Sands #237 Resort by RVA
Silver Sands on the Sea!
On the beach, sun-loungers, beach towels
Silver Sands on the Sea!
10.0 out of 10, Exceptional, (64)
"Our stay was amazing! A perfect beach condo for a family with young kids, short walk to the beautiful beach & pool! Heidi was a wonderful host, very thorough & so kind! This was our first visit to Longboat Key, we loved it! Would highly recommend this condo & hope to return in the future! "
The price is HK$2,335
HK$4,215 total
includes taxes & fees
16 Dec - 17 Dec
Silver Sands on the Sea!
The Beach on Longboat Key #221S Resort by RVA
Fridge, microwave, oven, stovetop
The Beach on Longboat Key #221S Resort by RVA
9.2 out of 10, Wonderful, (35)
"Fantastic location with terrific view of the ocean. Well furnished with a well equipped kitchen. Too bad the kitchen sink garbage disposal didn’t work, there were no wardrobe closets, & the toilet in the first bedroom kept running if the handle wasn’t giggled a few times."
The Beach on Longboat Key #221S Resort by RVA
Relax on the Coast This Winter!
Outdoor pool, a heated pool
Relax on the Coast This Winter!
10.0 out of 10, Exceptional, (103)
"First time to gulf side of Florida and not the last! Water so much calmer than Atlantic side for young family to play in. Dolphins/Manatees swimming by daily. Very memorable. In regards to the condo, very clean, was able to sleep family of 4 pretty easy. View of Gulf hard to beat. Pool very clean and not busy. Great stay and don't think you'll regret booking."
Relax on the Coast This Winter!
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
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
5 floor penthouse 60 feet from the sand Nov 16-23 Dec15-24open beach open
Property grounds
5 floor penthouse 60 feet from the sand Nov 16-23 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!"
5 floor penthouse 60 feet from the sand Nov 16-23 Dec15-24open beach open
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$1,315
HK$3,123 total
includes taxes & fees
24 Nov - 25 Nov
Beach view. Year-round Balcony Sunsets. Just renovated.
Pool View 2BR Condo at Gulf Tides
On the beach
Pool View 2BR Condo at Gulf Tides
9.0 out of 10, Wonderful, (2)
"Based on photos and views we thought we had a beach front property, however it was on the other side of the street."
Pool View 2BR Condo at Gulf Tides
Gulf Getaway with Porch + Direct Beach Access!
Beach nearby
Gulf Getaway with Porch + Direct Beach Access!
9.2 out of 10, Wonderful, (35)
"We had an awesome time at Longboat Key. It’s our favorite place and this was a perfect location to the beach, and the shops at St. Armand’s Circle. We will def book again and again!"
Gulf Getaway with Porch + Direct Beach Access!
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, (228)
"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 !!,
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, (7)
"Spacious condo and appreciated the layout for privacy between the MBR and the twin bedroom. Enjoyed the porch access off the MBR and the FR. Spacious/ updated kitchen also with another separate balcony and breakfast table. Incredibly private and quiet. Perfect walk across the street to the beach ( no life guard beach but you have several public beaches within 15 mins either in Anna Marie island or at Lido beach). The pool is clean and warm. So loved the evening entertainment with the pod of...
2BR Walk to the Beach Across the Street- Bay Views!
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

The St. Regis Longboat Key Resort
Exterior
The St. Regis Longboat Key Resort
5.0 star property
10.0 out of 10, Exceptional, (9)
"Beautiful new hotel"
The price is HK$5,946
HK$7,203 total
includes taxes & fees
15 Dec - 16 Dec
The St. Regis Longboat Key Resort
Zota Beach Resort
Breakfast, lunch and dinner served
Zota Beach Resort
4.0 star property
9.0 out of 10, Wonderful, (1000)
"very nice area"
The price is HK$1,786
HK$2,349 total
includes taxes & fees
8 Dec - 9 Dec
Zota Beach Resort
The Resort at Longboat Key Club
Exterior
The Resort at Longboat Key Club
4.0 star property
8.8 out of 10, Excellent, (635)
"Beautiful clean room. Very comfortable and well equipped. Would stay here in a heartbeat! "
The price is HK$2,935
HK$3,668 total
includes taxes & fees
2 Dec - 3 Dec
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.
Beautiful view of the beach with palm trees

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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?

Tiny House modeled after the yellow lifeguard stand on famous Siesta Key Beach: This holiday home rental outside of Longboat Key offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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?

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.