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Search Vacation Homes in Longboat Key

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In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Longboat Key vacation homes

Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
$355 nightly
The price is $402
Jan 4 - Jan 5, 2026
Total with taxes and fees
Siesta Heron Suites & Villas
Outdoor dining
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

Vacation Home in Sunny Shores

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
United States
RHEA
$471 nightly
The price is $526
Jan 4 - Jan 5, 2026
Total with taxes and fees
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Terrace/patio
The Hideaways at Point Pleasant (Palm Side)

Vacation Home in Bradenton

The Hideaways at Point Pleasant (Palm Side)
10.0 out of 10, Exceptional, (169)
"perfect location and size for what we were looking for"
United States
michael w.
$251 nightly
The price is $258
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Hideaways at Point Pleasant (Palm Side)
Smart TV, Netflix, streaming services
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Vacation Home in Sarasota

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
9.4 out of 10, Exceptional, (17)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
$213 nightly
The price is $238
Jan 12 - Jan 13, 2026
Total with taxes and fees
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Beach
Waterfront Retreat — Canal front, Pool, Putting Green, Beach Gear — 2BR/2BA

Vacation Home in Bradenton

Waterfront Retreat — Canal front, Pool, Putting Green, Beach Gear — 2BR/2BA
10.0 out of 10, Exceptional, (9)
"Cottage cheese as wonderful It had everything we could possibly need and more. Very relaxing and comfortable and accommodating. Hostess was responsive and attentive. Hope to have an opportunity to stay again!!"
United States
Wendy
$384 nightly
The price is $428
Dec 23 - Dec 24
Total with taxes and fees
Waterfront Retreat — Canal front, Pool, Putting Green, Beach Gear — 2BR/2BA
Smart TV, stereo
Charming home near Anna Maria Island with Jacuzzi

Vacation Home in Bradenton

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!"
United States
Kyle S.
$265 nightly
The price is $296
Dec 28 - Dec 29
Total with taxes and fees
Charming home near Anna Maria Island with Jacuzzi
Beach nearby, sun loungers, beach towels
Beautiful Blue Beach House Kids & Pets OK! MARCH 2026 SPECIALS!

Vacation Home in Bradenton

Beautiful Blue Beach House Kids & Pets OK! MARCH 2026 SPECIALS!
10.0 out of 10, Exceptional, (33)
"We were visiting Florida to celebrate my nephews birthday at the beach! We enjoyed the house and the beach! The family had a great time!"
United States
Eileen G.
$522 nightly
The price is $582
Dec 21 - Dec 22
Total with taxes and fees
Beautiful Blue Beach House Kids & Pets OK! MARCH 2026 SPECIALS!
Terrace/patio
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Vacation Home in Bradenton

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
9.4 out of 10, Exceptional, (67)
"Great place to stay!"
United States
Wendi B.
$125 nightly
The price is $139
Dec 24 - Dec 25
Total with taxes and fees
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Beach
Paradise Cove -- A perfect Beach Getaway

Vacation Home in Bradenton

Paradise Cove -- A perfect Beach Getaway
10.0 out of 10, Exceptional, (139)
"A great place to stay! They allowed us early check in which was great so we had ample time to settle in and prepare for the week. We had decided to eat in more and this was the perfect place for that! We were able to grill and cook, and hang out in the pool in a spacious backyard!"
United States
Andi J.
$404 nightly
The price is $451
Dec 23 - Dec 24
Total with taxes and fees
Paradise Cove -- A perfect Beach Getaway
Outdoor pool, a heated pool
Backyard Oasis & Resort Style Pool

Vacation Home in Bradenton

Backyard Oasis & Resort Style Pool
10.0 out of 10, Exceptional, (43)
"The home was very comfortable and in a great location. Close to lots of amenities and quick to great beaches. "
United States
Eric H.
$403 nightly
The price is $449
Dec 22 - Dec 23
Total with taxes and fees
Backyard Oasis & Resort Style Pool
Terrace/patio
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Vacation Home in Southgate

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
10.0 out of 10, Exceptional, (69)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
$277 nightly
The price is $310
Jan 4 - Jan 5, 2026
Total with taxes and fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Beach
Little Charm-Close to Anna Maria Island-IMG Academy-Gt Bray Park

Vacation Home in Bradenton

Little Charm-Close to Anna Maria Island-IMG Academy-Gt Bray Park
10.0 out of 10, Exceptional, (16)
"Comfy clean private house great neighborhood totally relaxing close to good resturants and beaches will book again."
United States
john l.
$253 nightly
The price is $283
Dec 21 - Dec 22
Total with taxes and fees
Little Charm-Close to Anna Maria Island-IMG Academy-Gt Bray Park
Property grounds
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Vacation Home in Sabal Harbour

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
2.0 star property
10.0 out of 10, Exceptional, (21)
"Everything was great!"
United States
Lisa and Colin M.
$330 nightly
The price is $368
Jan 13 - Jan 14, 2026
Total with taxes and fees
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Dining
[escape to paradise] siesta key beach getaway

Vacation Home in Siesta Key

[escape to paradise] siesta key beach getaway
9.8 out of 10, Exceptional, (24)
"Clean and comfortable. "
United States
Laney
$420 nightly
The price is $432
Jan 6 - Jan 7, 2026
Total with taxes and fees
[escape to paradise] siesta key beach getaway
Outdoor dining
The Mermaid at Tiny House Siesta

Vacation Home in Sarasota

The Mermaid at Tiny House Siesta
2.0 star property
10.0 out of 10, Exceptional, (2)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
$236 nightly
The price is $263
Dec 21 - Dec 22
Total with taxes and fees
The Mermaid at Tiny House Siesta
Outdoor dining
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Vacation Home in The Meadows

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
10.0 out of 10, Exceptional, (18)
"Fun place "
United States
Maureen
$249 nightly
The price is $277
Dec 24 - Dec 25
Total with taxes and fees
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
Fridge, microwave, oven, stovetop
5bdr newly remodeled house, heated pool & minutes to Siesta Key beach!

Vacation Home in South Sarasota

5bdr newly remodeled house, heated pool & minutes to Siesta Key beach!
9.8 out of 10, Exceptional, (33)
"The property is pretty big and has lots of room for a family that is vacationing. The area is close by to the beach and other things you may need like grocery stores and restaurants. It was an easy check in process and the place was clean. Tons of towel available and kitchen has everything you need! It’s a wonderful place with the amazing pool. Would highly recommend to anyone with a big family/group!"
United States
Lester C.
$741 nightly
The price is $828
Jan 3 - Jan 4, 2026
Total with taxes and fees
5bdr newly remodeled house, heated pool & minutes to Siesta Key beach!
Fridge, microwave, oven, stovetop
Downtown Bradenton Bliss: 3-Bed Apartment

Vacation Home in Bradenton

Downtown Bradenton Bliss: 3-Bed Apartment
9.6 out of 10, Exceptional, (22)
"Nice apartment for a small group"
United States
Franklin H.
$311 nightly
The price is $348
Dec 21 - Dec 22
Total with taxes and fees
Downtown Bradenton Bliss: 3-Bed Apartment
A heated pool
Luxury Pool Family Home Near Siesta Key/DT-3BR/2BA

Vacation Home in Kensington Park

Luxury Pool Family Home Near Siesta Key/DT-3BR/2BA
10.0 out of 10, Exceptional, (12)
"Great property, from the layout, furnishings, location and the POOL!! Without a doubt my best experience renting a VRBO."
United States
Jason J.
$376 nightly
The price is $422
Dec 23 - Dec 24
Total with taxes and fees
Luxury Pool Family Home Near Siesta Key/DT-3BR/2BA
Fridge, microwave, oven, stovetop
Downtown Escape! All new! Cute Villa in Sarasota!

Vacation Home in Central Sarasota

Downtown Escape! All new! Cute Villa in Sarasota!
8.8 out of 10, Excellent, (15)
"Good, close everything, quiet area"
United States
Paola C.
$288 nightly
The price is $288
Jan 6 - Jan 7, 2026
Total with taxes and fees
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

The Resort at Longboat Key Club

The Resort at Longboat Key Club

10/10 Excellent
"Everything Perfect!"
Tomas 3-night trip
Posted 9 days ago
The Resort at Longboat Key Club

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Longboat Key Vacation Homes information

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