A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Villas in Longboat Key

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Longboat Key villas

A single-story house with a white exterior, a dark roof, and a front door.

1. Lakefront 2BR Bradenton Rental Near IMG & Beaches

Lakefront 2BR Bradenton Rental Near IMG & Beaches
South Bradenton
8.8 out of 10, Excellent, (3 reviews)
"Very clean. No tissues or napkins🤔. Recommend pump hand soap instead of little bars. Also, 2 outdoor chaises were ripped and 1 out of 2 outdoor chairs was broken and unable to use the.."
United States
Laura
$228 nightly
The price is $242
Oct 28 - Oct 29
Total with taxes and fees
Lakefront 2BR Bradenton Rental Near IMG & Beaches
A serene lakeside setting with large trees and a white gazebo.

2. Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
Bradenton
9.8 out of 10, Exceptional, (30 reviews)
"The host was welcoming, and the amenities were great. We liked staying in that part of town."
United States
Perry W.
$263 nightly
The price is $294
Oct 11 - Oct 12
Total with taxes and fees
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly
A resort with a swimming pool, a covered patio, and a view of the ocean.

3. Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!
Bradenton
10.0 out of 10, Exceptional, (39 reviews)
"This was a great place to stay. Easy access to everything the area has to offer."
United States
Terri B.
$263 nightly
The price is $294
Oct 11 - Oct 12
Total with taxes and fees
Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!
A bicycle parked outside a building with a 'Hello' mat at the entrance.

4. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (43 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
$255 nightly
The price is $260
Oct 11 - Oct 12
Total with taxes and fees
[Beach Elements] pool view withprivate beach access
A dining area with a table and chairs, a green wall with a sign, and a view of palm trees and greenery.

5. Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly

Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
Bradenton
10.0 out of 10, Exceptional, (39 reviews)
"Very nice place and quiet. Enjoyed the secluded pool and the variety of plants and flowers everywhere. The Riverwalk was nice too."
United States
Craig C.
$263 nightly
The price is $294
Oct 11 - Oct 12
Total with taxes and fees
Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly
A sunlit balcony with a round glass table and wicker chairs, overlooking a well-maintained lawn and a house in the background.

6. Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
Sarasota
9.6 out of 10, Exceptional, (27 reviews)
"Excellent stay. Very clean and facilities were great "
United Kingdom
Jennie A.
$361 nightly
The price is $402
Oct 12 - Oct 13
Total with taxes and fees
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

7. SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
Sarasota
9.4 out of 10, Exceptional, (51 reviews)
"The condo is beautifully furnished and equipped with everything we needed. It was very comfortable and we would definitely stay there again."
United States
Sharon M.
$448 nightly
The price is $499
Oct 11 - Oct 12
Total with taxes and fees
SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
A swimming pool with a clear view of the ocean, surrounded by palm trees and a white fence.

8. Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio
Sarasota
10.0 out of 10, Exceptional, (21 reviews)
"Nice place and location. I would love to stay again."
United States
Jason M.
Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Patio
A multi-story hotel with a pool, beachside location, and a parking area.

9. NEW!~ Beach Front/Heated Pool! Coconuts 107

NEW!~ Beach Front/Heated Pool! Coconuts 107
Holmes Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great property, location and host …worth the price. Enjoy your stay as much as we did !!"
United States
Zulett L.
$634 nightly
The price is $706
Nov 1 - Nov 2
Total with taxes and fees
NEW!~ Beach Front/Heated Pool! Coconuts 107
A residential property with a driveway leading to a house, surrounded by well-maintained lawns and large trees with hanging moss.

10. Heated Pool • Sleeps 25 • Pickle/Bball • Theater

Heated Pool • Sleeps 25 • Pickle/Bball • Theater
Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"Great spot to have for a team playing in IMG events."
United States
Adam D.
$811 nightly
The price is $905
Oct 13 - Oct 14
Total with taxes and fees
Heated Pool • Sleeps 25 • Pickle/Bball • Theater
A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

11. BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
Sarasota
9.6 out of 10, Exceptional, (53 reviews)
"We loved staying here!! Having the garage was a really great bonus especially if you're going to the beach a lot! Pool was super nice and very close so that was great too! I really liked all the beach towels provided as well! Really great and nice place!"
United States
Misty S.
$468 nightly
The price is $522
Oct 11 - Oct 12
Total with taxes and fees
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!
A patio with a round table and chairs, a blue umbrella, and a view of a building with a balcony.

12. 1 Bedroom/1 Bath Villa (Ground Level) - Unit 11

1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
Casey Key
$206 nightly
The price is $229
Oct 12 - Oct 13
Total with taxes and fees
1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
A residential house with a fenced front yard, a parked car, and a palm tree.

13. Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
South Village
9.6 out of 10, Exceptional, (63 reviews)
"Close to everything, beautiful beach, clean property, pictures and description very accurate. Can’t wait to come back!"
United States
Karyn C.
$270 nightly
The price is $301
Oct 13 - Oct 14
Total with taxes and fees
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
A modern kitchen with white cabinets, a dining area with a round table and chairs, and large windows offering a view of greenery.

14. ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8

ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
Casey Key
10.0 out of 10, Exceptional, (4 reviews)
"Had a very relaxing time. Nice short walk to the beach"
United States
Mitch K.
$221 nightly
The price is $246
Oct 20 - Oct 21
Total with taxes and fees
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
A swimming pool with lounge chairs and a hammock, surrounded by a metal roof and lush greenery.

15. Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool

Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool
Nokomis
10.0 out of 10, Exceptional, (4 reviews)
"Everything was excellent! I would rent this again if the opportunity were there!"
United States
Sue H.
$767 nightly
The price is $855
Oct 11 - Oct 12
Total with taxes and fees
Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool
A building with a mural of birds and flowers on the side.

16. 2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A

2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
Casey Key
10.0 out of 10, Exceptional, (1 review)
"Perfect getaway"
United States
Joseph K.
$340 nightly
The price is $379
Oct 12 - Oct 13
Total with taxes and fees
2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
A house with a vibrant fish mural on the side, a paved pathway, and a small garden area with palm trees.

17. 2 Bedroom/2 Bath Villa (Ground Level) - Unit 7

2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
Casey Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean and updated cottage across the street from beach and walking distance to two restaurants. Responsive management and easy to work with. Quiet sleeping . Nice stay"
United States
Joanne K.
$350 nightly
The price is $390
Oct 19 - Oct 20
Total with taxes and fees
2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
Outdoor dining

18. 3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B

3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
Casey Key
10.0 out of 10, Exceptional, (1 review)
"The escape at Casey key was a great place to stay , was clean rooms were nice and updated and look forward to next Memorial Day weekend"
United States
Roger B.
$457 nightly
The price is $509
Nov 2 - Nov 3
Total with taxes and fees
3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
A modern living room with a leather sofa, a glass coffee table, and a dining area with a white table and chairs.

19. 2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C

2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
Casey Key
$340 nightly
The price is $379
Oct 13 - Oct 14
Total with taxes and fees
2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

10/10 Excellent
"Beach view and staff"
Alexis 2-night trip
Posted 9 hours ago
The St. Regis Longboat Key Resort

Find out more about Longboat Key

Longboat Key Villas information

Number of reviews
293
Accommodation
7 Villas
Lowest Price
$229
Highest Price
$905

Frequently asked questions

Why book your villa in Longboat Key with Expedia?
We think planning a vacation should be hassle-free, so if you're on the lookout for villas at the right price, Expedia has your back. Stick to the budget and select an all-inclusive stay, or splurge on a high-end villa to spoil your favorite people. Our search filters make it simple to find an escape in Longboat Key that suits your needs.
How can I find cheap villas in Longboat Key?
Expedia can help you search for cheap villas in Longboat Key. Use our convenient filter tool to choose budget, star rating and amenities to refine your search and find the perfect stay in a matter of clicks.

Explore a world of travel with Expedia