Location

Dates

Guests

Vacation rentals in Siesta Key, Florida, United States

Eclectic painted house

Plush furniture

Easy Access Living Area

Plenty of Seating

356 Azure

3 bedrooms·2 baths

Venice • Florida

$ 740,15 USD totaal voor 7 nachten

1–8 dec 2026

Lovely Lakeview Golf Club Condo image 1

Lovely Lakeview Golf Club Condo image 2

Lovely Lakeview Golf Club Condo image 3

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Lovely Lakeview Golf Club Condo image 5

Lovely Lakeview Golf Club Condo

2 bedrooms·2 baths

Bradenton • Florida

5(2 reviews)

$ 2.587,70 USD totaal voor 30 nachten

23 sep – 23 okt 2026

Unit 379

2 bedrooms·2 baths

Venice • Florida

4.6(30 reviews)

$ 5.508,75 USD totaal voor 30 nachten

31 mrt – 30 apr 2027

Unit 171

2 bedrooms·2 baths

Venice • Florida

4.67(9 reviews)

$ 5.593,50 USD totaal voor 30 nachten

31 mrt – 30 apr 2027

Unit 270

2 bedrooms·2 baths

Venice • Florida

$ 3.096,20 USD totaal voor 29 nachten

30 apr – 29 mei 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

$ 609,28 USD totaal voor 4 nachten

23–27 sep 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 totaal voor 7 nachten

23–30 sep 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ nacht(excl. kosten & belastingen)

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

$ 595,00 USD totaal voor 3 nachten

29 sep – 2 okt 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 totaal voor 7 nachten

23–30 sep 2026

Freshly harvested coconuts await your arrival for every person in your booking. (No additional charge). So plan to grab a coconut, set up your beach chair and put your feet in the white sands of Anna Maria Island. Cheers to a relaxing getaway!

Cozy but comfortable living room area.

Main bedroom with queen bed with calm blue accents and comfortable bedding.

2nd bedroom with a twin bed over full bunkbed. Closet space for storage.

Back patio sitting area with comfortable plush sectional sofa and arm chairs facing park and small mangrove preserve.

Coconuts included!+Family Friendly!+Close to Beach

2 bedrooms·2 baths

Holmes Beach • Florida

5(1 review)

$ 1.820,40 USD totaal voor 7 nachten

22–29 okt 2026

the Seaside 21 image 1

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the Seaside 21

2 bedrooms·2 baths

Holmes Beach • Florida

4.77(22 reviews)

$280 – $680/ nacht(excl. kosten & belastingen)

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

Gorgeous Beach Home with heated pool

3 bedrooms·3 baths

Holmes Beach • Florida

5(9 reviews)

$ 14.029,39 USD totaal voor 28 nachten

23 sep – 21 okt 2026

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa

Fun in the sun starts here - Hosted by RentAnnaMaria

Sunset Views from Shore to Please! - Hosted by RentAnnaMaria

Shore to Please - Hosted by RentAnnaMaria

Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths

Anna Maria • Florida

5(13 reviews)

$565 – $1.956/ nacht(excl. kosten & belastingen)

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 2

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 1

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 3

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 4

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 5

Quiet 3BD/2BA Home near Warm Mineral Springs Park

3 bedrooms·2 baths

North Port • Florida

4.92(12 reviews)

$126/ nacht(excl. kosten & belastingen)

Spotless & Tranquil Bungalow (Allergen Friendly)

Ra the Tortoise, he loves cucumbers so bring some snackies!

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

1 bedroom·1 bath

Parrish • Florida

5(82 reviews)

$ 718,80 USD totaal voor 3 nachten

10–13 nov 2026

Entire home in North Port, Florida

Entire home in North Port, Florida

Entire home in North Port, Florida

Entire home in North Port, Florida

Entire home in North Port, Florida

Entire home in North Port, Florida

4 bedrooms·1 bath

North Port • Florida

5(25 reviews)

$ 560,00 USD totaal voor 3 nachten

23–26 sep 2026

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

2 bedrooms·2 baths

North Port • Florida

$ 866,00 USD totaal voor 3 nachten

23–26 sep 2026

3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3 bedrooms·2 baths

North Port • Florida

$ 840,00 USD totaal voor 3 nachten

23–26 sep 2026

Coral cottage 2 miles to the beach bring your boat image 1

Coral cottage 2 miles to the beach bring your boat image 2

Coral cottage 2 miles to the beach bring your boat image 3

Coral cottage 2 miles to the beach bring your boat image 4

Coral cottage 2 miles to the beach bring your boat image 5

Coral cottage 2 miles to the beach bring your boat

2 bedrooms·1 bath

Englewood • Florida

$76 – $138/ nacht(excl. kosten & belastingen)

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

3 bedrooms·2 baths

Englewood • Florida

$ 832,50 USD totaal voor 3 nachten

23–26 sep 2026

Simple Old Florida Style Home image 1

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Simple Old Florida Style Home image 5

Bring your motorboat:Simple Old Florida Style Home

2 bedrooms·2 baths

Englewood • Florida

$43 – $106/ nacht(excl. kosten & belastingen)

4BR - Heated Pool and Lanai

4BR - Heated Pool and Lanai

4BR - Heated Pool and Lanai

4BR - Heated Pool and Lanai

4BR - Heated Pool and Lanai

4BR - Heated Pool and Lanai

4 bedrooms·2 baths

North Port • Florida

$ 1.135,79 USD totaal voor 3 nachten

23–26 sep 2026

3BR Home with Pool & Parking, Solar Power

3BR Home with Pool & Parking, Solar Power

3BR Home with Pool & Parking, Solar Power

3BR Home with Pool & Parking, Solar Power

3BR Home with Pool & Parking, Solar Power

3BR Home with Pool & Parking, Solar Power

3 bedrooms·2 baths

Venice • Florida

$ 734,50 USD totaal voor 3 nachten

23–26 sep 2026