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Vacation rentals in Holmes Beach, 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 gesamt für 3 Nächte

21.–24. Sept. 2026

Screened heated salt pool, hot tub and patio. Includes new smart TV, patio furniture, picnic table and chaise lounge chairs.

Relax in our bubbling, heated salt hot tub!

Beaches + Htd Pool/Spa + Fenced Yard + Game Room! image 3

Master bedroom with new king bed, smart TV, private attached bathroom, ceiling fan and double closets.

Bedroom offers 2 new twin beds and 1 new full bed. Also includes new smart TV and ceiling fan.

AMI Beaches + Heated Salt Pool + Spa + Large Yard

3 bedrooms·2 baths

Bradenton • Florida

5(49 reviews)

1.650,00 $ USD gesamt für 3 Nächte

13.–16. Sept. 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 gesamt für 182 Nächte

7. Sept. 2026 – 8. März 2027

Welcome to Paradise

Welcome to Paradise

Welcome to Paradise

Welcome to Paradise

Welcome to Paradise

Welcome to Paradise

3 bedrooms·2 baths

Bradenton • Florida

718,65 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

Sitting Area w/fireplace and desk

Floorplan layout

Workspace w/2GB Fiber Internet

Full kitchen w/new appliances

Coffee Bar w/K-cups, tea, sugar

Bradenton Boho Bungalow

3 bedrooms·2 baths

Bradenton • Florida

1.008,00 $ USD gesamt für 3 Nächte

7.–10. Sept. 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 gesamt für 120 Nächte

7. Sept. 2026 – 5. Jan. 2027

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

1.116,44 $ USD 1.071,92 $ USD gesamt für 3 Nächte

12.–15. Sept. 2026

32” TV with streaming device Comfortable couch.

Kitchen, diningroom, livingroom area

Gulf Coast Paradise Hideaway

Queen bed, night stand with usb plug, and lamp. 32”TV with streaming device sits on top of Armoire with plenty of storage. Bedroom does have closet with hangers.

Gulf Coast Paradise Hideaway

Gulf Coast Paradise Hideaway

1 bedroom·1 bath

Palmetto • Florida

989,85 $ USD 911,32 $ USD gesamt für 7 Nächte

7.–14. Sept. 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)

1.266,73 $ USD gesamt für 3 Nächte

23.–26. Sept. 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 gesamt für 3 Nächte

22.–25. Sept. 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)

781,96 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

6 bedrooms·4 baths

Bradenton • Florida

1.532,16 $ USD gesamt für 3 Nächte

7.–10. Sept. 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 gesamt für 3 Nächte

7.–10. Sept. 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 gesamt für 3 Nächte

13.–16. Sept. 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 gesamt für 3 Nächte

7.–10. Sept. 2026

Casa Milly image 1

Casa Milly image 2

Casa Milly image 3

Casa Milly image 4

Casa Milly image 5

Casa Milly

2 bedrooms·1 bath

Bradenton • Florida

5(36 reviews)

$150/ Nacht(zzgl. Gebühren & Steuern)

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

3 bedrooms·2 baths

Sarasota • Florida

4.89(18 reviews)

1.406,85 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

350 feet of waterfront and a pair that extended out 250 feet into the river.

The house all lite up at night. Very peaceful

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

4 bedrooms·4 baths

Ellenton • Florida

5(3 reviews)

3.596,55 $ USD gesamt für 5 Nächte

19.–24. Okt. 2026

Kostenlose Stornierung

Our home is in the left side of the picture.

The front of our home.

Established 2019

Craig House with Heated Pool

3 bedrooms·2 baths

Bradenton • Florida

4.8(107 reviews)

1.150,60 $ USD 1.104,12 $ USD gesamt für 5 Nächte

10.–15. Sept. 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 gesamt für 60 Nächte

7. Sept. – 6. Nov. 2026

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths

Bradenton • Florida

1.320,00 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths

Bradenton • Florida

3.871,68 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

Landscape lighting and firepit in the front of the house

View of the canal in the back of the house

Sunrise over the pool and covered outdoor seating.

Large pull out sectional facing the fireplace and flatscreen TV

Living room with pull out couch, flatscreen and dining table

Tropi-Casa

4 bedrooms·2 baths

Bradenton • Florida

862,50 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

Kostenlose Stornierung

Property grounds

Beautiful 2 Bed/2 Bath Cozy Cottage Retreat â Your Home Away From Home

1 bedroom·1 bath

Sarasota • Florida

713,00 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026