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Vacation rentals in Siesta Key, Florida, United States

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

18.–23. Nov. 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 gesamt für 29 Nächte

18. Nov. – 17. 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

2.723,76 $ USD gesamt für 3 Nächte

18.–21. Nov. 2026

Eclectic painted house

Plush furniture

Easy Access Living Area

Plenty of Seating

356 Azure

3 bedrooms·2 baths

Venice • Florida

819,25 $ USD gesamt für 7 Nächte

1.–8. Dez. 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 gesamt für 30 Nächte

1.–31. Mai 2027

Relax by the fire pit and enjoy sunset views in this private backyard

Let the kids play putt putt golf, bocce ball and more while you relax in the refreshing pool. Summertime paradise awaits!

The Salty Palm

3 bedrooms·2 baths

Bradenton • Florida

5(43 reviews)

952,90 $ USD gesamt für 3 Nächte

18.–21. Nov. 2026

Unit 379

2 bedrooms·2 baths

Venice • Florida

4.6(30 reviews)

5.508,75 $ USD gesamt für 30 Nächte

31. März – 30. Apr. 2027

Unit 171

2 bedrooms·2 baths

Venice • Florida

4.67(9 reviews)

Unit 270

2 bedrooms·2 baths

Venice • Florida

3.096,20 $ USD gesamt für 29 Nächte

30. Apr. – 29. Mai 2027

sit back and relax on this cozy porch

bright ,cheerful open floor plan

cozy wraparound porch

updated fully equipped kitchen with new large sitting island

Tree house by the beach

1 bedroom·1 bath

Venice • Florida

667,52 $ USD gesamt für 4 Nächte

23.–27. Nov. 2026

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

Gulf Drive Living

2 bedrooms·1 bath

Holmes Beach • Florida

3.150,00 $ USD gesamt für 7 Nächte

18.–25. Nov. 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ Nacht(zzgl. Gebühren & Steuern)

Welcome to AMI Villa

Light up the night!

Spectacular night lights over the pool

Amazing rooftop screened in patio

Comfortable family-style living area

AMI Villa

3 bedrooms·3 baths

Holmes Beach • Florida

5(3 reviews)

3.022,36 $ USD gesamt für 7 Nächte

30. Nov. – 7. Dez. 2026

Relaxing and inviting private pool

Relaxing and inviting private pool

Relaxing and inviting private pool

Grill for guest use right outside the pool patio area

Sit back and relax on a newly added Leather sofa set watching a new 55” smart TV

Pool Villa by the Beach

2 bedrooms·2 baths

Venice • Florida

622,00 $ USD gesamt für 3 Nächte

18.–21. Nov. 2026

Float the afternoon away

Welcome to Under the Foxtails

Bright, open coastal living space

Stylish space to relax and chat

Modern beach style and comfort

Under the Foxtails

3 bedrooms·3 baths

Holmes Beach • Florida

2.357,70 $ USD gesamt für 7 Nächte

28. Nov. – 5. Dez. 2026

Front of the house tucked away in Florida greens

New heated pool

1 of 2 seating areas by the pool

New hotel style lounge chairs

Manasota Beach Vacation Villa

3 bedrooms·3 baths

Englewood • Florida

5(12 reviews)

1.912,37 $ USD gesamt für 7 Nächte

18.–25. Nov. 2026

Beautiful elevated home with private yard

Welcome to Rollin' with the Waves

Only five houses to the sand

Your tropical getaway awaits

Rollin' with the Waves

3 bedrooms·2½ baths

Holmes Beach • Florida

5(2 reviews)

2.526,33 $ USD gesamt für 7 Nächte

27. Nov. – 4. Dez. 2026

Resort-style relaxation in your own backyard

Sparkling and inviting year-round

Welcome to Aquamarine Oasis

Airy and light-filled space

Coastal-inspired kitchen with wraparound counters

Aquamarine Oasis

3 bedrooms·2½ baths

Holmes Beach • Florida

2.298,62 $ USD gesamt für 7 Nächte

18.–25. Nov. 2026

Stunning private yard and pool

Huge Holmes Beach home

So close to the beach

Spacious and welcoming foyer

Beachy Blue

4 bedrooms·4 baths

Holmes Beach • Florida

3.320,23 $ USD gesamt für 7 Nächte

27. Nov. – 4. Dez. 2026

Your private heated pool

Welcome to A Villa Paradise

Bright coastal charm awaits

Comfortable coastal living

Backyard just steps away

A Villa Paradise

3 bedrooms·2 baths

Holmes Beach • Florida

1.979,83 $ USD gesamt für 7 Nächte

28. Nov. – 5. Dez. 2026

Welcome to Palm Villa

All new furnishings

Newly remodeled dreamy villa

Palm Villa

2 bedrooms·2 baths

Holmes Beach • Florida

1.614,27 $ USD gesamt für 7 Nächte

18.–25. Nov. 2026

Relax on the patio

Welcome to Orchid Villa

Beautifully designed

Coastal blue hues

Cable TV in the living room

Orchid Villa

2 bedrooms·2 baths

Holmes Beach • Florida

1.614,27 $ USD gesamt für 7 Nächte

18.–25. Nov. 2026

Open seamless floor plan

Welcome to Blue Agave Villa

Newly remodeled dreamy villa

Dining table for 4

Blue Agave Villa

2 bedrooms·2 baths

Holmes Beach • Florida

5(1 review)

1.441,95 $ USD gesamt für 7 Nächte

18.–25. Nov. 2026

Welcome to Hibiscus Villa

Designer furnishings

Dining room for 4

Beautiful mid-century modern

Hibiscus Villa

1 bedroom·1 bath

Holmes Beach • Florida

1.509,65 $ USD gesamt für 7 Nächte

6.–13. Dez. 2026