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Vacation rentals in Longboat Key, Florida, United States

Featured

Private courtyard patio with dining for 4.

Private courtyard patio

Courtyard patio

Exterior detail

Comforts of Home in Secure Gated Community Just 2 Miles from Anna Maria Island

2 bedrooms·2 baths

Bradenton • Florida

5(2 reviews)

$6,302.00 USD total for 30 nights

Nov 17 – Dec 17, 2026

Welcome to The Beach on Longboat Key, Unit 224!

Located mid-island, gulfside!

It's the good life.

White sand and turquoise waters!

Condo With a View 4: On the Beach!

1 bedroom·1 bath

Longboat Key • Florida

4.96(26 reviews)

$994.40 USD total for 3 nights

Nov 18 – 21, 2026

Guest Bedroom converted to a king bed

Sea Club III #4 2B / 2B Direct Beachfront Condo by RVA

2 bedrooms·2 baths

Longboat Key • Florida

$1,820.00 USD total for 5 nights

Nov 17 – 22, 2026

Lush and tropical!

Welcome to Silver Sands on Longboat Key!

Stroll north or south on the beach or just sit and wait for the sunrise or sunset -- you've got time.

Silver Sands Gulf Beach Resort!

White sandy beach - ideal!

Tropical Beach Condo!

1 bedroom·1 bath

Longboat Key • Florida

5(11 reviews)

$994.40 USD total for 3 nights

Nov 23 – 26, 2026

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

2 bedrooms·2 baths

Longboat Key • Florida

$25,878.00 USD total for 120 nights

Nov 18, 2026 – Mar 18, 2027

balcony + Gulf view

Living room with Gulf view

Beachfront Escape – Private Balcony, Gulf Views image 5

Panoramic Gulf View with Amazing Sunset.

1 bedroom·1 bath

Longboat Key • Florida

4.87(223 reviews)

$1,227.18 USD total for 3 nights

Nov 29 – Dec 2, 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1

Turtle Crawl Inn 64

1 bedroom·1 bath

Longboat Key • Florida

4.88(73 reviews)

$1,022.65 USD total for 3 nights

Nov 28 – Dec 1, 2026

Right on the beach.Renovated ground Floor unit 63. image 1

Right on the beach.Renovated ground Floor unit 63. image 5

Turtle Crawl Inn 63

0 bedrooms·1 bath

Longboat Key • Florida

4.74(88 reviews)

$836.20 USD total for 3 nights

Nov 30 – Dec 3, 2026

Gulf Access

4 bedrooms·4½ baths

Longboat Key • Florida

$2,000.00 USD total for 3 nights

Nov 18 – 21, 2026

Float the day away!

View from our lanai - straight on out!

The sweet life!

Condo with a View on Longboat Key

0 bedrooms·1 bath

Longboat Key • Florida

4.98(122 reviews)

$971.80 USD total for 3 nights

Nov 20 – 23, 2026

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

0 bedrooms·1 bath

Longboat Key • Florida

5(28 reviews)

$971.80 USD total for 3 nights

Nov 18 – 21, 2026

IMG Academy, Heated Pool, Huge Game Room & Golf! image 1

IMG Academy, Heated Pool, Huge Game Room & Golf! image 2

IMG Academy, Heated Pool, Huge Game Room & Golf! image 3

IMG Academy, Heated Pool, Huge Game Room & Golf! image 4

IMG Academy, Heated Pool, Huge Game Room & Golf! image 5

Sunny Bradenton Oasis, Pool/ Near Beaches & Golf!

4 bedrooms·2 baths

Bradenton • Florida

$1,151.47 USD $1,105.19 USD total for 3 nights

Dec 11 – 14, 2026

View of condo from Sarasota Bay.

View of complex from public beach/Coquina Beach

Sunrise over Sarasota Bay from condo decks/bedroom/living room

Sunset of the Gulf from condo and public beach/Coquina Beach

Sunrise/Sunset

2 bedrooms·2 baths

Bradenton Beach • Florida

$2,815.25 USD total for 7 nights

May 13 – 20, 2027

The Surof House

The Surof House

The Surof House

The Surof House

The Surof House

The Surof House

2 bedrooms·1 bath

Bradenton Beach • Florida

5(2 reviews)

$1,792.20 USD total for 3 nights

Nov 18 – 21, 2026

Your private pool escape awaits

Welcome to Beach & Bay

Sunny days and spa nights

Steps from both beach and bay

Welcome to your coastal getaway

Beach & Bay

7 bedrooms·7 baths

Bradenton Beach • Florida

$6,465.05 USD total for 4 nights

Nov 17 – 21, 2026

Community Pool & Courts

Condo 6 miles from breathtaking Anna Maria Island

Condo 6 miles from breathtaking Anna Maria Island

View from Lanai

Ground Floor Condo

Condo 6 miles from breathtaking Anna Maria Island

2 bedrooms·2 baths

Bradenton • Florida

$12,700.00 USD total for 182 nights

Nov 18, 2026 – May 19, 2027

My Sunny home on the Bay. image 1

My Sunny home on the Bay. image 2

My Sunny home on the Bay. image 4

My Sunny home on the Bay. image 5

My Sunny home on the Bay. image 6

My Sunny home on the Bay.

2 bedrooms·2 baths

Bradenton • Florida

4.98(273 reviews)

$800.35 USD total for 3 nights

Apr 1 – 4, 2027

My Peaceful place on the bay. image 1

My Peaceful place on the bay. image 2

My Peaceful place on the bay. image 3

My Peaceful place on the bay. image 4

My Peaceful place on the bay. image 5

My Peaceful place on the bay.

2 bedrooms·2 baths

Bradenton • Florida

4.99(187 reviews)

$549.49 USD $511.86 USD total for 3 nights

Nov 22 – 25, 2026

Casa Bonita image 1

Casa Bonita image 2

Casa Bonita image 3

Casa Bonita image 4

Casa Bonita image 5

Casa Bonita

3 bedrooms·3½ baths

Bradenton Beach • Florida

5(13 reviews)

$3,671.37 USD total for 5 nights

Nov 29 – Dec 4, 2026

Tranquility on the bay. image 1

Tranquility on the bay. image 2

Tranquility on the bay. image 3

Tranquility on the bay. image 4

Tranquility on the bay. image 5

Tranquility on the bay.

2 bedrooms·2 baths

Bradenton • Florida

4.99(159 reviews)

$599.21 USD total for 3 nights

Nov 29 – Dec 2, 2026

Making Waves

3 bedrooms·3 baths

Bradenton Beach • Florida

5(1 review)

$4,194.00 USD total for 4 nights

Nov 28 – Dec 2, 2026

Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 2

Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 3

Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 4

Luxury 2BR/2BA Condo Minutes from Beaches & IMG image 5

Luxury 2BR/2BA Condo Minutes from Beaches & IMG

2 bedrooms·2 baths

Bradenton • Florida

5(37 reviews)

$553.40 USD total for 3 nights

Nov 17 – 20, 2026

Tiki Time-Beach Boutique Rentals

Spacious living area

Chefs dream! Gourmet kitchen

Beautiful dining room

Tiki Time

4 bedrooms·2½ baths

Bradenton • Florida

$1,342.25 USD total for 3 nights

Nov 17 – 20, 2026

Screened lanai with table and chairs

Our ground floor corner unit

Loungers in front of building

View down the beach

Aerial view of building from Gulf

Beachfront Condo in Bradenton Beach – Ground Floor

1 bedroom·1 bath

Bradenton Beach • Florida

$1,701.56 USD total for 3 nights

Dec 20 – 23, 2026