Holiday Homes in Longboat Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Longboat Key holiday homes

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

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Super beautiful beach and heated pool. So nice. My room had zero view but it was fine. You are there for beach. Not the room. It was clean. Pool was so clear and warm! Coffee pot, refrig and micro all good. Bed was comfy. No sink in apt except bathroom sink. Awkward. But fine. Sunrise to sunset . "
United States
Pamela
The price is AU$489
includes taxes & fees
4 Mar - 5 Mar
Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Massive Beach House, 6BR 8BA, Heated Pool, Pickleball, Hot tub, Gym, Sleeps 22

Massive Beach House, 6BR 8BA, Heated Pool, Pickleball, Hot tub, Gym, Sleeps 22
Palma Sola
10.0 out of 10, Exceptional, (61 reviews)
"Loved this big roomy house. 17 of us and didn’t feel crowded at all!! We enjoyed everything— the pool, theatre "
United States
Patti M.
The price is AU$2,518
includes taxes & fees
9 Mar - 10 Mar
Massive Beach House, 6BR 8BA, Heated Pool, Pickleball, Hot tub, Gym, Sleeps 22

Boutique Waterfront Cottage • Pool & Putting Green • Near AMI Beaches • 2BR/2BA

Boutique Waterfront Cottage • Pool & Putting Green • Near AMI Beaches • 2BR/2BA
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"This was a super cute house, the property was just as great. Everything was super clean and nice. We had a wonderful stay!"
United States
Christopher H.
The price is AU$635
includes taxes & fees
27 Mar - 28 Mar
Boutique Waterfront Cottage • Pool & Putting Green • Near AMI Beaches • 2BR/2BA

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (60 reviews)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is AU$912
includes taxes & fees
6 Mar - 7 Mar
Siesta Key Island Rentals

Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool & Outdoor Living

Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool & Outdoor Living
Bradenton
10.0 out of 10, Exceptional, (73 reviews)
"Absolutely love this place, nice and kind tucked away but two minutes from the beach, the pool and the outdoor grilling area made it totally worth it "
United States
Robert M.
The price is AU$1,038
includes taxes & fees
11 Mar - 12 Mar
Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool & Outdoor Living

Winter Special! !Only 4 miles to AMI! Huge Pool! NEW Hot Tub!

Winter Special! !Only 4 miles to AMI! Huge Pool! NEW Hot Tub!
Bradenton
9.8 out of 10, Exceptional, (45 reviews)
"Property was clean and the kitchen was well stocked with appliances! The kids loved the pool and AMI was a short drive and absolutely beautiful! Our family would definitely stay again in the furture!"
United States
Tiffany S.
The price is AU$1,265
includes taxes & fees
3 Mar - 4 Mar
Winter Special! !Only 4 miles to AMI! Huge Pool! NEW Hot Tub!

Beautiful Blue Beach House Kids & Pets OK

Beautiful Blue Beach House Kids & Pets OK
Bradenton
9.8 out of 10, Exceptional, (37 reviews)
"The host was the best, I highly recommend this house. You will have everything you need to make your stay comfortable. "
United States
Miera G.
The price is AU$952
includes taxes & fees
5 Mar - 6 Mar
Beautiful Blue Beach House Kids & Pets OK

2 Bed with Beach Supplies, Trailer Space, Walk to Beach, Near IMG Academy

2 Bed with Beach Supplies, Trailer Space, Walk to Beach, Near IMG Academy
Cortez
The price is AU$731
includes taxes & fees
9 Mar - 10 Mar
2 Bed with Beach Supplies, Trailer Space, Walk to Beach, Near IMG Academy

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Sunny Shores
9.4 out of 10, Exceptional, (35 reviews)
"Excellent for a family trip."
United States
RHEA
The price is AU$773
includes taxes & fees
3 Mar - 4 Mar
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (13 reviews)
"Great location, clean, good communication. "
United States
Alexandra P.
The price is AU$1,170
includes taxes & fees
12 Mar - 13 Mar
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (16 reviews)
"It was and clean. However, not if enough hot water heater for 2 to shower every day. "
United States
lori
The price is AU$2,217
includes taxes & fees
8 Mar - 9 Mar
Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Lulu's Key House Kemp Ridley 1/1 Downstairs

Lulu's Key House Kemp Ridley 1/1 Downstairs
3.5 star property
Siesta Key Village
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful place. Very clean, easy check-in, wonderful location"
United States
Christine
The price is AU$1,022
includes taxes & fees
4 Mar - 5 Mar
Lulu's Key House Kemp Ridley 1/1 Downstairs

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
The price is AU$746
includes taxes & fees
10 Mar - 11 Mar
Beachy Sarasota Duplex

The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (170 reviews)
"perfect location and size for what we were looking for"
United States
michael w.
The price is AU$365
includes taxes & fees
3 Mar - 4 Mar
The Hideaways at Point Pleasant (Palm Side)

Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12
Central Sarasota
10.0 out of 10, Exceptional, (13 reviews)
"Great place perfect location to the marina, and downtown area. Highly recommended thanks "
United States
Domingo B.
The price is AU$732
includes taxes & fees
9 Mar - 10 Mar
Luxury House Walking Distance to Ocean - Sleeps 12

Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool

Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool
Siesta Key
8.8 out of 10, Excellent, (54 reviews)
"Great family trip at this rental property, close to very nice beaches and great pool and gazebo at unit too!"
United States
Betsy S.
The price is AU$909
includes taxes & fees
3 Mar - 4 Mar
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool

Cottage on the canal

Cottage on the canal
Bradenton
10.0 out of 10, Exceptional, (149 reviews)
"Great place to stay, super convenient location. The neighborhood was super quiet day and night. The interior is spacious, more than enough room for a family and more. The pool was one of the cleanest pools I’ve been in on a vacation stay, great job to whomever maintains it. Our favorite part of the house is the exterior, the pool area and the dock. Overall super happy choosing this house, we would choose it again."
United States
Tom K.
The price is AU$1,101
includes taxes & fees
15 Mar - 16 Mar
Cottage on the canal

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Anna Maria
9.8 out of 10, Exceptional, (14 reviews)
"Really nice cottages, and mgt on-site and super responsive and helpful!"
United States
Jerry A.
The price is AU$1,216
includes taxes & fees
9 Mar - 10 Mar
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Downtown Escape! All new! Cute Villa in Sarasota!

Downtown Escape! All new! Cute Villa in Sarasota!
Central Sarasota
8.8 out of 10, Excellent, (16 reviews)
"Good, close everything, quiet area"
United States
Paola C.
The price is AU$724
includes taxes & fees
10 Mar - 11 Mar
Downtown Escape! All new! Cute Villa in Sarasota!

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

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Sabal Harbour
9.8 out of 10, Exceptional, (27 reviews)
"Everything was great!"
United States
Lisa and Colin M.
The price is AU$561
includes taxes & fees
4 Mar - 5 Mar
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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

Longboat Key Holiday Homes information

Number of reviews
831
Accommodation
164 Holiday Homes
Lowest Price
AU$365
Highest Price
AU$2,518

Explore a world of travel with Expedia