Location

Dates

Guests

Vacation rentals in Longboat Key

Just at the bottom of the stairs! The beach awaits...!

Welcome to Silver Sands, Unit 256 on Longboat Key!

We're right on the Gulf! No need to cross a busy street to get to the beach!

A bird's eye view!

Silver Sands Gulf Beach Resort -- iconic, well-known (and loved!), old Florida charm, located on Gulf of Mexico Dr., beach side, just 35 units!

Tropical Beach Condo!

1 bedroom·1 bath

Longboat Key • Florida

5(11 reviews)

$1,153.60 USD total for 3 nights

Oct 16 – 19, 2026

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

Sep 29 – Oct 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)

$189 – $290/ night(excl. fees & taxes)

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)

$861.06 USD total for 3 nights

Sep 24 – 27, 2026

Gulf Access

4 bedrooms·4½ baths

Longboat Key • Florida

$60,500.00 USD total for 30 nights

Sep 23 – Oct 23, 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)

$1,333.40 USD total for 3 nights

Sep 23 – 26, 2026

Welcome to The Beach, Unit 222!

The Beach complex from the waterfront - only 15 units, nice and quiet!

View to the South - sit and stay a while!

Float the day away!

Condo with a View on Longboat Key

0 bedrooms·1 bath

Longboat Key • Florida

4.98(122 reviews)

$1,310.80 USD total for 3 nights

Sep 27 – 30, 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)

$1,141.30 USD total for 3 nights

Sep 23 – 26, 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

$853.15 USD $821.80 USD total for 3 nights

Sep 28 – Oct 1, 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

Sep 23 – 30, 2026

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)

$2,020.86 USD total for 3 nights

Sep 27 – 30, 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

Sep 23, 2026 – Mar 24, 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)

$119 – $185/ night(excl. fees & taxes)

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)

$111 – $195/ night(excl. fees & taxes)

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)

$2,699.00 USD total for 5 nights

Sep 27 – Oct 2, 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)

$119 – $195/ night(excl. fees & taxes)

Making Waves

3 bedrooms·3 baths

Bradenton Beach • Florida

5(1 review)

$4,194.00 USD total for 4 nights

Sep 29 – Oct 3, 2026

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

2 bedrooms·2 baths

Longboat Key • Florida

$8,425.50 USD total for 60 nights

Sep 23 – Nov 22, 2026

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!

3-story Townhouse (Living areas on 2nd and 3rd Floors)

DazeOffAMI - Gulf & Bay Views, Walk to Bridge St!

3 bedrooms·2½ baths

Bradenton Beach • Florida

5(149 reviews)

$2,682.59 USD total for 7 nights

Sep 26 – Oct 3, 2026

Dans Florida Condos Sandy Slippers at Runaway Bay

Dans Florida Condos Sandy Slippers at Runaway Bay

Dans Florida Condos Sandy Slippers at Runaway Bay

Dans Florida Condos Sandy Slippers at Runaway Bay

Dans Florida Condos Sandy Slippers at Runaway Bay

Dans Florida Condos Sandy Slippers at Runaway Bay

2 bedrooms·2 baths

Bradenton Beach • Florida

$2,467.80 USD total for 7 nights

Sep 23 – 30, 2026

Dans Florida Condos Sea Esta at Runaway Bay

Dans Florida Condos Sea Esta at Runaway Bay

Dans Florida Condos Sea Esta at Runaway Bay

Dans Florida Condos Sea Esta at Runaway Bay

Dans Florida Condos Sea Esta at Runaway Bay

Dans Florida Condos Sea Esta at Runaway Bay

1 bedroom·1 bath

Bradenton Beach • Florida

$1,777.76 USD total for 7 nights

Sep 23 – 30, 2026

Dans Florida Condos Dolphin Bay at Runaway Bay

Dans Florida Condos Dolphin Bay at Runaway Bay

Dans Florida Condos Dolphin Bay at Runaway Bay

Dans Florida Condos Dolphin Bay at Runaway Bay

Dans Florida Condos Dolphin Bay at Runaway Bay

Dans Florida Condos Dolphin Bay at Runaway Bay

2 bedrooms·2 baths

Bradenton Beach • Florida

$2,353.00 USD total for 7 nights

Sep 23 – 30, 2026

Dans Florida Condos Ocean Pearl at Runaway Bay

Dans Florida Condos Ocean Pearl at Runaway Bay

Dans Florida Condos Ocean Pearl at Runaway Bay

Dans Florida Condos Ocean Pearl at Runaway Bay

Dans Florida Condos Ocean Pearl at Runaway Bay

Dans Florida Condos Ocean Pearl at Runaway Bay

2 bedrooms·2 baths

Bradenton Beach • Florida

$2,334.52 USD total for 7 nights

Sep 23 – 30, 2026

Dans Florida Condos Sea Dream at Runaway Bay

Dans Florida Condos Sea Dream at Runaway Bay

Dans Florida Condos Sea Dream at Runaway Bay

Dans Florida Condos Sea Dream at Runaway Bay

Dans Florida Condos Sea Dream at Runaway Bay

Dans Florida Condos Sea Dream at Runaway Bay

2 bedrooms·2 baths

Bradenton Beach • Florida

$2,169.88 USD total for 7 nights

Sep 23 – 30, 2026