Sarasota Skyline At Sunrise

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
In two months
In three months
In four months

Our top choices for Longboat Key villas

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
9.6 out of 10, Exceptional, (49 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.
$403 nightly
The price is $448
Jun 17 - Jun 18
Total with taxes and fees
SPRING SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

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, (24 reviews)
"Such a relaxing villa just 15 minutes from Siesta Key! We had such a wonderful time relaxing, hanging at the pool, and visiting the local shops. If you’re looking for a place to stay, choose this condo, you will not regret 😊"
United States
Sommer
$355 nightly
The price is $395
Jun 17 - Jun 18
Total with taxes and fees
Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

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, (24 reviews)
"Great host, clean facilities, adequately equipped kitchen, great escape back yard, close to river walk with views of mile wide Manatee River. "
United States
William B.
$289 nightly
The price is $322
Jul 1 - Jul 2
Total with taxes and fees
Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

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, (36 reviews)
"Host was lovely and very accommodating. Very nice property."
United States
catherine M.
$281 nightly
The price is $314
Jun 17 - Jun 18
Total with taxes and fees
Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (33 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.
$331 nightly
The price is $339
Jun 21 - Jun 22
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

Heated Pool • Sleeps 32 • Pickle/Bball • Theater

Heated Pool • Sleeps 32 • 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.
$1,024 nightly
The price is $1,142
Jul 12 - Jul 13
Total with taxes and fees
Heated Pool • Sleeps 32 • Pickle/Bball • Theater

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, (3 reviews)
"Everything was excellent! I would rent this again if the opportunity were there!"
United States
Sue H.
$934 nightly
The price is $1,042
Jul 6 - Jul 7
Total with taxes and fees
Sea Glass Serenity, 3+2, Nokomis Beach, Heated Pool

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, (34 reviews)
"Nice place next to the river. It had everything we needed. Clean & had a great outdoor area. We felt very welcome and at home away from home. "
United States
Jill J.
$283 nightly
The price is $316
Jun 17 - Jun 18
Total with taxes and fees
Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly

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
$271 nightly
The price is $290
Jun 30 - Jul 1
Total with taxes and fees
Lakefront 2BR Bradenton Rental Near IMG & Beaches

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.6 out of 10, Exceptional, (43 reviews)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
$641 nightly
The price is $715
Jun 21 - Jun 22
Total with taxes and fees
Beautiful Bungalow with Pool and Bay Views!

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.
$327 nightly
The price is $364
Jun 17 - Jun 18
Total with taxes and fees
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8

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, (52 reviews)
"Beautiful apartment located near the beach and state parks"
United States
Eliot f.
$423 nightly
The price is $471
Jul 1 - Jul 2
Total with taxes and fees
BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

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

1 Bedroom/1 Bath Villa (Ground Level) - Unit 11
Casey Key
$327 nightly
The price is $364
Jun 21 - Jun 22
Total with taxes and fees
1 Bedroom/1 Bath Villa (Ground Level) - Unit 11

For family fun or a romantic escape close to sarasota and the area"s beaches

For family fun or a romantic escape close to sarasota and the area"s beaches
Bayshore Gardens
9.6 out of 10, Exceptional, (5 reviews)
"It seemed to be recently remodeled in excellent condition. Good safe location. Lots of room for a couple but had an extra bedroom so it would work great for a family. The outdoor area was huge with a great gas grill area. Lots of extra little touches like coffee tea chocolate andchampagne."
United States
Steve R.
$254 nightly
The price is $283
Jun 21 - Jun 22
Total with taxes and fees
For family fun or a romantic escape close to sarasota and the area"s beaches

Beachfront Paradise! Ground level with Heated pool

Beachfront Paradise! Ground level with Heated pool
Holmes Beach
10.0 out of 10, Exceptional, (2 reviews)
"Great place. We loved it!!!!!"
United States
Jill T.
$694 nightly
The price is $774
Jun 17 - Jun 18
Total with taxes and fees
Beachfront Paradise! Ground level with Heated pool

NEW!~ Beach Front/Heated Pool! Coconuts 107

NEW!~ Beach Front/Heated Pool! Coconuts 107
Holmes Beach
10.0 out of 10, Exceptional, (1 review)
"We had an amazing 5 days enjoying waterfront access and gorgeous sunsets. The bed was very comfortable and the condo was spotless. It was very convenient to have 2 chair and umbrella. Although we didn't use the pool, it was great to have available. We didn't eat dinner in, but if you do you will need to bring or purchase seasonings, etc. Would definitely stay here again. "
United States
cheryl m.
$1,098 nightly
The price is $1,226
Jun 30 - Jul 1
Total with taxes and fees
NEW!~ Beach Front/Heated Pool! Coconuts 107

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated
Sarasota
10.0 out of 10, Exceptional, (9 reviews)
"We enjoyed spending a week in this villa. It was cozy, very clean and perfect for our family. Great location... you can enjoy 3 different pools or the private beach aera. Looking forward to our next visit. "
United States
Beverly G.
$570 nightly
The price is $636
Jul 11 - Jul 12
Total with taxes and fees
Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated

Completely Remodeled- 150 Yards to Beach and Restaurants!

Completely Remodeled- 150 Yards to Beach and Restaurants!
South Village
10.0 out of 10, Exceptional, (42 reviews)
"Great unit—clean, well-equipped with everything we needed, including beach gear. Near a beautiful beach, great restaurants, and trolley. Owner was easy to work with. Looking forward to returning."
United States
Vicky C.
$385 nightly
The price is $428
Jun 24 - Jun 25
Total with taxes and fees
Completely Remodeled- 150 Yards to Beach and Restaurants!

Heated Pool and Spa • Outdoor Kitchen/Theater/Games

Heated Pool and Spa • Outdoor Kitchen/Theater/Games
South Bradenton
2.0 out of 10, (1 review)
"Where do I start. We arrived in the house to find there are not seven bedrooms, but six. The pool was not clean it had leaves and other items at the bottom as well as the hot tub had a used filter laying in it along with other debris and was cold. The hot tub took 24 hours to heat up. The house itself is very weird in the set up and the furniture inside. Looks like it was bought at a yard sale. The hot water on one side of the house did not work in one of the showers and one of the...
United States
William R.
$541 nightly
The price is $598
Jun 23 - Jun 24
Total with taxes and fees
Heated Pool and Spa • Outdoor Kitchen/Theater/Games

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, (61 reviews)
"Great place! Love having a private place to stay with all we need including great beach toys, chairs and umbrellas!"
United States
Tanya V.
$271 nightly
The price is $302
Jun 25 - Jun 26
Total with taxes and fees
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
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

Longboat Key Villas information

Number of reviews
19,271
Accommodation
9 Villas
Lowest Price
$77
Highest Price
$1,180

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