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Top Holiday Rentals in Longboat Key

Ground Floor, Steps to the Sand Silver Sands #243A Resort by RVA

8.6 out of 10, Excellent, (58)
"This is our second time staying at the Silver Sands. Very clean, nice people, nice amenities. "
The price is £219
includes taxes & fees
20 Jul - 21 Jul
Ground Floor, Steps to the Sand Silver Sands #243A Resort by RVA

Beachfront Bliss on Longboat Key- Steps to the sand

6.0 out of 10, (1)
"There’s good and not so good about this place! First of all, the location is amazing! The unit opens up to the pool area and is steps away from a gorgeous beach! Now, the not so good…. we arrived around 3:30am to find that the unit looked nothing like what the photos on the listing show. If you are seeing a bright white/grey decor and a separate small bedroom, you are seeing the wrong unit. We messaged the owner making sure we were in the correct unit bc the unit we were in was definitely not...
The price is £322
includes taxes & fees
3 Aug - 4 Aug
Beachfront Bliss on Longboat Key- Steps to the sand

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (33)
"A very comfortable stay in Siesta Key. Our apartment had been fully redeveloped since Hurricane Milton. Excellent job. Pool was really good. Nikes to ride. Kayaks to addle in the lagoon. All in allan exceptional choice. "
The price is £285
includes taxes & fees
10 Aug - 11 Aug
Siesta Heron Suites & Villas

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (1)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is £261
includes taxes & fees
22 Jul - 23 Jul
Charming Florida Beach Home w King Bed Patio

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

2.0 star property
10.0 out of 10, Exceptional, (18)
"Everything was great!"
The price is £247
includes taxes & fees
21 Jul - 22 Jul
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

9.6 out of 10, Exceptional, (35)
"Looking forward to staying there again."
The price is £337
includes taxes & fees
18 Jul - 19 Jul
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great vacation stay "
The price is £287
includes taxes & fees
17 Jul - 18 Jul
Siesta Key Island Rentals

Spring Special! New HOT TUB! Beach! Huge Private Pool & Game Room!

10.0 out of 10, Exceptional, (30)
"As wonderful as it appears. Great host."
Spring Special! New HOT TUB! Beach! Huge Private Pool & Game Room!

Charming home near Anna Maria Island with Jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
The price is £218
includes taxes & fees
22 Jul - 23 Jul
Charming home near Anna Maria Island with Jacuzzi

Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

3.0 star property
The price is £320
includes taxes & fees
19 Jul - 20 Jul
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches

2.0 star property
9.0 out of 10, Wonderful, (10)
"The bedrooms and bathrooms were spacious and also the closets. The kitchen was well-equipped. Overall a very comfortable and safe place to stay."
The price is £381
includes taxes & fees
28 Jul - 29 Jul
W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...

9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
The price is £404
includes taxes & fees
26 Jul - 27 Jul
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...

Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

10.0 out of 10, Exceptional, (20)
"Near beach and town."
The price is £680
includes taxes & fees
3 Aug - 4 Aug
Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

[lounge like locals] walk to siesta beach +bikes

9.8 out of 10, Exceptional, (20)
"Lovely stay at Siesta Key! Minute walk to beaches and restaurants. Very spacious and clean! Highly recommended "
The price is £276
includes taxes & fees
24 Jul - 25 Jul
[lounge like locals] walk to siesta beach +bikes

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (61)
"Very comfortable and perfect location to the airport! "
The price is £148
includes taxes & fees
13 Aug - 14 Aug
Casa Azul 2Bed/1Bath

Luxury Oasis Home 3BR 2Bath with Heated Pool

9.8 out of 10, Exceptional, (9)
"Great place to stay! Modern amenities, heated pool, very clean!! Would rent this again!"
The price is £339
includes taxes & fees
3 Aug - 4 Aug
Luxury Oasis Home 3BR 2Bath with Heated Pool

Game Room Florida Home

9.8 out of 10, Exceptional, (24)
"Always a great place to stay. We have a tournament a month- try to stay at the game room house!! "
The price is £346
includes taxes & fees
3 Aug - 4 Aug
Game Room Florida Home

Paradise Cove -- A perfect Beach Getaway

10.0 out of 10, Exceptional, (124)
"Our stay was amazing. The pictures were accurate. Maggie the host was great. The location of the property is just a short drive to Bradenton Beach. We will return for another stay. "
The price is £335
includes taxes & fees
23 Jul - 24 Jul
Paradise Cove -- A perfect Beach Getaway

Sunny Skies: Modern 2-Bedroom Home with Pool Near Bradenton Beach Awaits You!

9.6 out of 10, Exceptional, (30)
"If you're looking for near beach (10 minutes) with private pool this is good spot. Also very convenient to grocery stores and many other necessities. "
Sunny Skies: Modern 2-Bedroom Home with Pool Near Bradenton Beach Awaits You!
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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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 free 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 177 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.