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Vacation rentals in Longboat Key, Florida, United States

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 nætter

16.–19. okt. 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

$190/ nat(exkl. gebyrer & skatter)

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 nætter

29. sep.–2. okt. 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)

932,25 $ USD total for 3 nætter

28. sep.–1. okt. 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)

861,06 $ USD total for 3 nætter

24.–27. sep. 2026

Gulf Access

4 bedrooms·4½ baths

Longboat Key • Florida

$2.000/ nat(exkl. gebyrer & skatter)

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 nætter

24.–27. sep. 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 nætter

27.–30. sep. 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 nætter

24.–27. sep. 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 nætter

28. sep.–1. okt. 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

$325/ nat(exkl. gebyrer & skatter)

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 nætter

27.–30. sep. 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

$55/ nat(exkl. gebyrer & skatter)

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)

576,61 $ USD total for 3 nætter

24.–27. sep. 2026

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 nætter

24.–27. sep. 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)

2.699,00 $ USD total for 5 nætter

27. sep.–2. okt. 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)

610,51 $ USD total for 3 nætter

24.–27. sep. 2026

Making Waves

3 bedrooms·3 baths

Bradenton Beach • Florida

5(1 review)

4.194,00 $ USD total for 4 nætter

29. sep.–3. okt. 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 nætter

24. sep.–23. nov. 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 nætter

26. sep.–3. okt. 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 nætter

24. sep.–1. okt. 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 nætter

24. sep.–1. okt. 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 nætter

24. sep.–1. okt. 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 nætter

24. sep.–1. okt. 2026