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Vacation rentals in Holmes Beach, Florida, United States

Building Arial View

St Pete Beachside Condo

1 bedroom·1 bath

St. Pete Beach • Florida

5(3 reviews)

$ 1.297,68 USD totaal voor 5 nachten

23–28 okt 2026

Lovely Lakeview Golf Club Condo image 1

Lovely Lakeview Golf Club Condo image 2

Lovely Lakeview Golf Club Condo image 3

Lovely Lakeview Golf Club Condo image 4

Lovely Lakeview Golf Club Condo image 5

Lovely Lakeview Golf Club Condo

2 bedrooms·2 baths

Bradenton • Florida

5(2 reviews)

$ 2.825,00 USD totaal voor 30 nachten

1–31 mei 2027

Your favorite beach getaway (4)

Your favorite beach getaway (4)

Your favorite beach getaway (4)

Shared Laundry room located on 1st flooor

Your favorite beach getaway (4)

Your favorite beach getaway (4)

1 bedroom·1 bath

St. Pete Beach • Florida

5(3 reviews)

$ 1.606,00 USD totaal voor 6 nachten

23–29 okt 2026

Living room with Full Size sleep sofa

Private condo steps to beach (3)

Private condo steps to beach (3)

Newly remodeled bathroom as of 1/2024

Fully equipped kitchen

Private condo steps to beach (3)

1 bedroom·1 bath

St. Pete Beach • Florida

$ 1.511,70 USD totaal voor 6 nachten

23–29 okt 2026

Heated pool & spa

Bathroom 1 bath/shower

Bathroom 2 walk in shower

Heated Pool & Spa 3bd/2bth, near Siesta Key Beach

3 bedrooms·2 baths

Sarasota • Florida

$ 810,00 USD totaal voor 3 nachten

23–26 okt 2026

Waterfront 3BR 2 1/2 Bath, Amazing View-Sunrises!

3 bedrooms·2½ baths

St. Pete Beach • Florida

5(3 reviews)

$ 13.750,00 USD totaal voor 30 nachten

1–31 jan 2027

Family home on Golf Course image 1

Family home on Golf Course image 2

Family home on Golf Course image 4

Family home on Golf Course image 5

Family home on Golf Course

4 bedrooms·4 baths

Bradenton • Florida

$ 2.550,00 USD totaal voor 5 nachten

23–28 okt 2026

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

Waterfront Pool Home w/Golf membership, near beach

3 bedrooms·2 baths

Bradenton • Florida

$ 8.052,00 USD totaal voor 29 nachten

8 nov – 7 dec 2026

Toes in the water...

Kitchen / eating area

Catch sunsets like this just a 2 min walk from your front door.

St Pete Beach Condo - Steps to the Sand! Pool, Pickleball, Dual Gulf & Bay Views

2 bedrooms·2 baths

St. Pete Beach • Florida

$ 1.130,00 USD totaal voor 3 nachten

23–26 okt 2026

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

2 bedrooms·2 baths

Manatee County • Florida

$ 13.700,00 USD totaal voor 60 nachten

23 okt – 22 dec 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths

Sarasota • Florida

5(2 reviews)

$ 11.383,59 USD $ 10.850,06 USD totaal voor 7 nachten

19–26 dec 2026

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

St Pete Beach Condo (2)

1 bedroom·1½ baths

St. Pete Beach • Florida

$ 18.060,00 USD $ 16.269,00 USD totaal voor 90 nachten

23 okt 2026 – 21 jan 2027

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

St Pete Beach Condo (1)

1 bedroom·1½ baths

St. Pete Beach • Florida

$ 19.504,80 USD totaal voor 90 nachten

2 nov 2026 – 31 jan 2027

Waterfront Key West–style community, Stunning water views, glowing sunsets, and a laid-back island vibe ✨

King SUITE! Calm, Spacious and inviting, this KING bedroom features a plush KING-sized bed, with new bedding , dresser and 2 nighstands offering comfort and style for a restful night’s sleep in a beautifully designed space.

Stunning waterfront views from the bright, open-concept living room, dining area, and fully equipped kitchen. The perfect space to relax, gather, and make unforgettable memories by the water.

Nothing compares to swimming in the pool while breathing in the fresh ocean breeze.

WELCOME to your own private scenic beach, offering exclusive access to pristine sands and tranquil waters. Perfect for relaxing in solitude, soaking up the sun, or enjoying peaceful oceanfront moments.

Waterfront Escape | Private Beach + 2 Pools

1 bedroom·1 bath

St. Petersburg • Florida

4.5(16 reviews)

$ 4.379,88 USD $ 4.225,30 USD totaal voor 30 nachten

23 okt – 22 nov 2026

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

2 bedrooms·2 baths

St. Petersburg • Florida

4.67(12 reviews)

$ 3.049,30 USD totaal voor 28 nachten

23 okt – 20 nov 2026

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

3 bedrooms·2 baths

Sarasota • Florida

$ 500,00 USD totaal voor 3 nachten

23–26 okt 2026

Palmetto House

3 bedrooms·3 baths

Sarasota • Florida

$ 2.230,86 USD $ 2.036,45 USD totaal voor 7 nachten

9–16 nov 2026

Steps from the beach! Newly listed updated unit image 1

Cross the parking spaces and dunes... to have your toes in the sand. Famous beach bars /restaurants to the left of the peach condos on the left.

Steps from the beach! Newly listed updated unit image 3

primary bedroom

primary bedroom

Steps from the beach! Newly listed updated unit

2 bedrooms·1 bath

St. Pete Beach • Florida

4.94(16 reviews)

$ 1.317,00 USD totaal voor 3 nachten

23–26 okt 2026

We have it all - beautiful beach and comfortable accommodation

Living room with queen sofa bed and upgraded mattress. Comfortable rocking chairs. Smart TV - guests can use their Netflix, Amazon movie's, Hulu, etc. Basic cable is available in the living room TV as well.

Heated community pool for residents and guests only. Hours of operations: 9am-10pm.

The condo and the beach - very short walk across beach parking lot. St. Pete Beach - votes #1 beach in US by TripAdvisor in 2021.

Living room, kitchen and the coffee station

Condo in Beachfront Resort with Heated Pool

1 bedroom·1 bath

St. Pete Beach • Florida

5(29 reviews)

$ 614,72 USD totaal voor 3 nachten

23–26 okt 2026

FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6

Your boutique Mediterranean-style 2BR bungalow (4 beds) — resort level comfort + coastal charm!

Your own private resort — located on a serene palm-lined lain in Sarasota’s coveted coastal district!

Half a mile to the Siesta Key, home of Siesta Key Beach — experience the sugar white sands of America’s #1 beach!

A Mediterranean-meets-California retreat where natural textures and curated details invite beautiful living

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath

Sarasota • Florida

5(2 reviews)

$ 2.248,70 USD totaal voor 7 nachten

24–31 okt 2026

Living room from hallway

Seasonal Golf-Course Townhome in The Meadows – Fully Furnished

Fully equipped kitchen opens on courtyard

Patio with golf view

Seasonal Golf-Course Townhome in The Meadows – Fully Furnished

3 bedrooms·2 baths

Sarasota • Florida

4(1 review)

$ 14.362,15 USD totaal voor 75 nachten

2 jan – 18 mrt 2027

Siesta Key beach

Dusk view of front of building

Front door and porch area

Front door and sliding glass doors

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath

Sarasota • Florida

$ 890,90 USD totaal voor 3 nachten

23–26 okt 2026

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths

Siesta Key • Florida

5(26 reviews)

$ 14.950,00 USD totaal voor 28 nachten

15 apr – 13 mei 2027

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

3 bedrooms·2 baths

St. Petersburg • Florida

4.9(51 reviews)

$ 1.497,00 USD totaal voor 3 nachten

27–30 okt 2026