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Our top choices for Longboat Key vacation 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 ¥26,997
¥55,120 total
includes taxes & fees
Mar 4 - Mar 5
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 ¥144,409
¥283,028 total
includes taxes & fees
Mar 9 - Mar 10
Massive Beach House, 6BR 8BA, Heated Pool, Pickleball, Hot tub, Gym, Sleeps 22

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 ¥33,551
¥92,858 total
includes taxes & fees
Mar 2 - Mar 3
Sleeps 10 | Tropical 3BR Retreat w/ Heated Pool & Outdoor Living

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 ¥51,729
¥87,827 total
includes taxes & fees
Mar 2 - Mar 3
Siesta Key Island Rentals

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 ¥20,411
¥69,865 total
includes taxes & fees
Mar 27 - Mar 28
Boutique Waterfront Cottage • Pool & Putting Green • Near AMI Beaches • 2BR/2BA

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)
"We needed a relaxing retreat from a very busy summer of work. This place was perfect! It was in an excellent location, the house was clean, the pool and hot tub were AMAZING and the communication with our host was super easy!! I would highly recommend this little piece of paradise, you will not be disappointed! We would definitely stay here again!"
United States
Leslie A.
The price is ¥58,987
¥136,854 total
includes taxes & fees
Mar 2 - Mar 3
Winter Special! !Only 4 miles to AMI! Huge Pool! NEW Hot Tub!

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 ¥151,447
¥245,959 total
includes taxes & fees
Mar 8 - Mar 9
Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

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 ¥24,411
¥87,869 total
includes taxes & fees
Mar 2 - Mar 3
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

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 ¥32,614
¥104,681 total
includes taxes & fees
Mar 5 - Mar 6
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 ¥38,853
¥83,190 total
includes taxes & fees
Mar 11 - Mar 12
2 Bed with Beach Supplies, Trailer Space, Walk to Beach, Near IMG Academy

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 ¥72,860
¥134,401 total
includes taxes & fees
Mar 12 - Mar 13
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

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 ¥31,585
¥83,754 total
includes taxes & fees
Mar 8 - Mar 9
Beachy Sarasota Duplex

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

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
River District
10.0 out of 10, Exceptional, (64 reviews)
"Awesome location, beautiful house, wonderful host."
United States
Michele D.
The price is ¥22,627
¥62,357 total
includes taxes & fees
Apr 1 - Apr 2
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

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 ¥65,018
¥118,401 total
includes taxes & fees
Mar 4 - Mar 5
Lulu's Key House Kemp Ridley 1/1 Downstairs

Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12
Central Sarasota
10.0 out of 10, Exceptional, (12 reviews)
"Great place perfect location to the marina, and downtown area. Highly recommended thanks "
United States
Domingo B.
The price is ¥40,573
¥83,331 total
includes taxes & fees
Mar 9 - Mar 10
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 ¥50,556
¥100,519 total
includes taxes & fees
Mar 2 - Mar 3
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool

Charming home near Anna Maria Island with Jacuzzi

Charming home near Anna Maria Island with Jacuzzi
Bradenton
9.8 out of 10, Exceptional, (17 reviews)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
United States
Kyle S.
The price is ¥26,685
¥49,301 total
includes taxes & fees
Mar 2 - Mar 3
Charming home near Anna Maria Island with Jacuzzi

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 ¥66,367
¥139,216 total
includes taxes & fees
Mar 9 - Mar 10
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

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 ¥18,710
¥38,558 total
includes taxes & fees
Mar 2 - Mar 3
The Hideaways at Point Pleasant (Palm Side)

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 ¥51,340
¥81,302 total
includes taxes & fees
Mar 10 - Mar 11
Downtown Escape! All new! Cute Villa in Sarasota!
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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Top Longboat Key Hotel Reviews

Find out more about Longboat Key

Longboat Key Vacation Homes information

Number of reviews
671
Accommodation
164 Vacation Homes
Lowest Price
¥38,558
Highest Price
¥283,028