Holiday Homes in Longboat Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Longboat Key

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

9.6 out of 10, Exceptional, (32)
"We enjoyed our stay. Close to the beach. enjoyed the pool.Kitchen was perfect we were able to make breakfast and dinner."
The price is AU$442
includes taxes & fees
28 Aug - 29 Aug
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIAL

Cozy condotel with King Bed, WiFi, great pool, fitness room and much more!

10.0 out of 10, Exceptional, (2)
"This unit was well stocked and very nicely decorated. The bed was comfy! We needed to be close to our clinic and this suited our needs well. It was great going to the pool and walking along the marina. The restaurant/tiki bar right on site was fun and the food was good. It was so nice not having to drive anywhere for dinner after a long day! We would definitely stay in this unit again. The owners were super quick to respond and helpful."
The price is AU$257
includes taxes & fees
28 Aug - 29 Aug
Cozy condotel with King Bed, WiFi, great pool, fitness room and much more!

Heated Pool, Strong WI-FI, TV, Tiki Bar & Grill, Boat and Kayak Rentals

8.6 out of 10, Excellent, (9)
"I was looking for a nice place close to the airport and my events, and that's what I found."
The price is AU$284
includes taxes & fees
9 Sept - 10 Sept
Heated Pool, Strong WI-FI, TV, Tiki Bar & Grill, Boat and Kayak Rentals

Condo with a View 4: Top Floor, Oceanfront!

10.0 out of 10, Exceptional, (2)
"I absolutely loved this Condo! The view was so amazing, the beach it just a few steps away. The pictures are 100% accurate if not better. The host was attentive and so nice, she even left me muffins and drinks at my door for when I arrived and they were delicious! Will definitely be coming back again. Thanks for the great stay! I highly recommend this place for sure! "
Condo with a View 4: Top Floor, Oceanfront!

Beachfront Bliss on Longboat Key- Steps to the sand

7.0 out of 10, Good, (2)
"Location was perfect for the beach access we were looking for. The unit was small with a few minor glitches, but it was clean.The property and pool were well mantained and there were no issues with check-in."
The price is AU$648
includes taxes & fees
9 Sept - 10 Sept
Beachfront Bliss on Longboat Key- Steps to the sand

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is AU$914
includes taxes & fees
31 Aug - 1 Sept
Siesta Heron Suites & Villas

Charming home near Anna Maria Island with Jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
The price is AU$425
includes taxes & fees
9 Sept - 10 Sept
Charming home near Anna Maria Island with Jacuzzi

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is AU$513
includes taxes & fees
16 Sept - 17 Sept
Charming Florida Beach Home w King Bed Patio

Relaxing 2BR Florida Home Close to Beach

2.0 star property
The price is AU$577
includes taxes & fees
9 Sept - 10 Sept
Relaxing 2BR Florida Home Close to Beach

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is AU$500
includes taxes & fees
3 Sept - 4 Sept
Siesta Key Island Rentals

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 AU$693
includes taxes & fees
9 Sept - 10 Sept
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

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

2.0 star property
10.0 out of 10, Exceptional, (18)
"Great stay! Nice place and location!"
The price is AU$537
includes taxes & fees
9 Sept - 10 Sept
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Paradise Cove -- A perfect Beach Getaway

10.0 out of 10, Exceptional, (128)
"This property was excellent. It suited all of our needs. Plenty of space and sleeping arrangements. Excellent communication. Excellent location. Kids had a blast in the pool, overall experience was amazing. "
The price is AU$638
includes taxes & fees
28 Aug - 29 Aug
Paradise Cove -- A perfect Beach Getaway

Bradenton Breeze

4.0 star property
6.0 out of 10, (2)
"It was good! "
The price is AU$471
includes taxes & fees
28 Aug - 29 Aug
Bradenton Breeze

Sun and Sand Lodge - 2 bd/1 bath near SRQ Airport!

The price is AU$547
includes taxes & fees
9 Sept - 10 Sept
Sun and Sand Lodge - 2 bd/1 bath near SRQ Airport!

Adorable Cottage moments to beach w/ pool, beach gear, bikes

9.8 out of 10, Exceptional, (11)
"Loved how the cottage is wqlking distance to the beach and also restaurants."
The price is AU$992
includes taxes & fees
9 Sept - 10 Sept
Adorable Cottage moments to beach w/ pool, beach gear, bikes

Charming Florida bungalow with pool and fenced-in yard.

10.0 out of 10, Exceptional, (36)
"We will be back! The house was clean and comfortable and very homey with games and books. We really appreciated all the extras, like water bottles waiting in the fridge and beach chairs and toys available to use in the garage. The pool was great, too. "
The price is AU$526
includes taxes & fees
11 Sept - 12 Sept
Charming Florida bungalow with pool and fenced-in yard.

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

10.0 out of 10, Exceptional, (54)
"We loved our stay "
The price is AU$555
includes taxes & fees
28 Aug - 29 Aug
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

Heated Pool 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 AU$711
includes taxes & fees
9 Sept - 10 Sept
Heated Pool Florida Home

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

3.0 star property
The price is AU$670
includes taxes & fees
9 Sept - 10 Sept
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Find out more about Longboat Key

Find out more about Longboat Key

Longboat Key Holiday Homes information

Number of reviews
322
Accommodation
162 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia