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Vacation rentals in Holmes Beach, Florida, United States

Relax and unwind in the covered seating area next to the pool, with comfortable outdoor furniture and a dining table

The incredible outdoor space truly sets this home apart.The new saltwater pool with a spa and sunshelf were completed in spring 2023.

Guests love that the living room flows directly out to the pool and lanai!

The kitchen includes a backsplash made of real shells, floating driftwood shelves made by a local artist, granite countertops, and all the appliances and accessories you will need.

The primary bedroom has a king bed, armoire and dresser for clothing storage, and direct access to the swimming pool.

Palma Janoli

3 bedrooms·2 baths

Bradenton • Florida

5(110 reviews)

2.567,16 $ USD gesamt für 3 Nächte

26.–29. Dez. 2026

Palma Rosa and Palma Janoli

The incredible outdoor space truly sets this home apart.The new saltwater pool with a spa and sunshelf were completed in spring 2023.

Palma Rosa's outdoor space includes a covered outdoor seating/dining area with an outdoor TV

Easily walk between the two houses.

Relax and unwind in the covered seating area next to the pool, with comfortable outdoor furniture and a dining table

Palma Rosa and Palma Janoli

6 bedrooms·4 baths

Bradenton • Florida

6.126,75 $ USD gesamt für 3 Nächte

26.–29. Dez. 2026

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

Gulf Coast Home w/Private Pool Near AMI & Beaches

4 bedrooms·3 baths

Bradenton • Florida

5(22 reviews)

3.424,96 $ USD gesamt für 5 Nächte

23.–28. Okt. 2026

Aerial shot of house and pool.

Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

Aerial of patio & pool

Pool & outdoor area at night.

Pool & Hot tub at night.

Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 bedrooms·2 baths

Bradenton • Florida

5(50 reviews)

1.880,00 $ USD gesamt für 3 Nächte

25.–28. Dez. 2026

Poolside meets game time

From the heated pool and hot tub to the game courts, fire pit, and outdoor lounging areas—our backyard is designed for the ultimate getaway experience.

Soak in the hot tub before or after a refreshing dip in the pool—perfect for relaxing mornings, sunset wind-downs, or starlit evenings.

The ultimate bunk room & play space! Featuring 6 queen-size bunk beds, this fun-filled room is perfect for kids, teens, and groups to sleep, play, and make unforgettable memories together.

Enjoy our spacious mini golf course—perfect for friendly competition, family fun, and laid-back afternoons right at the property.

7mi to AMI w/ Pickleball+Golf | Htd Pool+Tiki Hut

5 bedrooms·3 baths

Bradenton • Florida

2.280,98 $ USD gesamt für 3 Nächte

26.–29. Okt. 2026

Dive into your own private paradise! Welcome to your "Happy Place" with a private fully-fenced backyard, surrounded by mature palm trees and a spacious HEATED SALTWATER POOL, plus tons of color changing lights!

Covered patio with fire pit, dining area & BBQ—perfect evenings

The sunlit Family Room with sparkling swimming pool views, an expansive L-shaped couch, oversized ottoman, children's books, games, and Smart TV for endless entertainment options, make it the perfect hub for relaxation and family fun!

Screened pool oasis with loungers, travertine deck & sunset views

Stainless LG appliances
Quartz countertops
Child & baby-friendly amenities
Fully Stocked

Heated Pool+5mile to AMI & IMG+Kid Friendly

4 bedrooms·2 baths

Bradenton • Florida

5(114 reviews)

1.380,23 $ USD gesamt für 4 Nächte

23.–27. Okt. 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 gesamt für 3 Nächte

23.–26. Okt. 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)

1.850,00 $ USD gesamt für 3 Nächte

30. Okt. – 2. Nov. 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

23. Okt. 2026 – 23. Apr. 2027

2 Homes, 1 Private Pool | Near IMG & AMI

Jenga and the Washer game help let non-pool lovers still be part of the action.

The twilight is beautiful with no bugs and lots of time to have a night swim.

2 Homes, 1 Private Pool | Near IMG & AMI

Putting Green with adjustable Putters and Balls Available or Bring your Own

2 Homes, 1 Private Pool | Near IMG & AMI

4 bedrooms·3 baths

Bradenton • Florida

1.053,25 $ USD gesamt für 3 Nächte

23.–26. Okt. 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 gesamt für 5 Nächte

23.–28. Okt. 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 gesamt für 3 Nächte

23.–26. Okt. 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ Nacht(zzgl. Gebühren & Steuern)

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

23.–26. Okt. 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(24 reviews)

500,00 $ USD gesamt für 3 Nächte

23.–26. Okt. 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

23.–26. 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

25.878,00 $ USD gesamt für 120 Nächte

23. Okt. 2026 – 20. Feb. 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

915,30 $ USD 880,84 $ USD gesamt für 3 Nächte

8.–11. Nov. 2026

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)

5.810,00 $ USD gesamt für 30 Nächte

23. Okt. – 22. Nov. 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

23.–30. Okt. 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 gesamt für 3 Nächte

16.–19. Nov. 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

26.–29. 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)

815,86 $ USD gesamt für 3 Nächte

27.–30. Okt. 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

2.696,96 $ USD gesamt für 3 Nächte

23.–26. Okt. 2026