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Vacation rentals in Siesta Key, Florida, United States

Commonwealth

4 bedrooms·3½ baths

Siesta Key • Florida

$ 1.496,25 USD totaal voor 3 nachten

30 nov – 3 dec 2026

5 min walk to the best Beach in America! image 1

5 min walk to the best Beach in America! image 2

5 min walk to the best Beach in America! image 3

5 min walk to the best Beach in America! image 4

5 min walk to the best Beach in America! image 5

5 min walk to the best Beach in America!

1 bedroom·2 baths

Siesta Key • Florida

$ 3.120,00 USD $ 2.823,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Treasure Boat

3 bedrooms·2 baths

Siesta Key • Florida

$ 1.065,75 USD totaal voor 3 nachten

28 nov – 1 dec 2026

Our Private Beach with chairs and umbrellas all included!!

Just a day at our private beach

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

2 bedrooms·1½ baths

Sarasota County • Florida

$ 1.200,01 USD totaal voor 7 nachten

29 nov – 6 dec 2026

506 Siesta

2 bedrooms·2 baths

Sarasota • Florida

Private beach access is 350 steps from property gate

Incredible Pool

Gated access and covered parking

Enjoy meals inside or on the balcony

Beach, Bay, Food, Fun - 2BD/2BA

2 bedrooms·2 baths

Siesta Key • Florida

4.67(9 reviews)

$ 1.488,48 USD totaal voor 5 nachten

27 nov – 2 dec 2026

Back yard with new pool 15x28 ft

Pool Depth 3ft-5ft

Casa Blanca Ranch Home near Siesta Key Beach

15x28 ft pool with spa/hot tub

New Sun Shelves with pool chaises

Casa Blanca Ranch Home near Siesta Key Beach

3 bedrooms·2 baths

Sarasota • Florida

5(18 reviews)

$ 2.264,65 USD totaal voor 5 nachten

18–23 nov 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

Living room with pullout couch

Siesta Key beach

Dusk view of front of building

Front door and porch area

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath

Sarasota • Florida

$ 745,76 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Drone view of Crescent Property.

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths

Siesta Key • Florida

5(76 reviews)

$ 5.422,84 USD $ 5.043,79 USD totaal voor 7 nachten

20–27 dec 2026

Best Deals on Siesta Key image 1

Best Deals on Siesta Key image 2

Best Deals on Siesta Key image 3

Best Deals on Siesta Key image 4

Best Deals on Siesta Key image 5

Best Deals on Siesta Key

1 bedroom·1 bath

Sarasota • Florida

4.72(155 reviews)

$ 532,00 USD totaal voor 3 nachten

22–25 nov 2026

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

2 bedrooms·2 baths

Sarasota • Florida

$ 722,00 USD totaal voor 3 nachten

18–21 nov 2026

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

Prime Location: 1 Mile to Siesta Key South Bridge

2 bedrooms·1 bath

Sarasota • Florida

$ 3.900,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Heated Saltwater Pool

The pool and surrounding area features enough lighting to enjoy the Florida evenings in style!

Catch the game on the 75" TV from the HOT TUB!

Newly remodeled kitchen with new stainless steel appliances (refrigerator, induction cook top, built in microwave/oven and dishwasher).

Living Room featuring a large sectional sofa and a 55" smart TV. Sit and enjoy the abundance of natural light.

The Funky Fish House

2 bedrooms·2 baths

Sarasota • Florida

4.99(156 reviews)

$ 1.375,73 USD totaal voor 5 nachten

27 nov – 2 dec 2026

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

1 bedroom·1 bath

Sarasota • Florida

5(71 reviews)

$ 427,00 USD totaal voor 3 nachten

28 nov – 1 dec 2026

Sun Haven House - 4 mi to beach! 2 beds/2 baths image 1

Well equipped kitchen with full size appliances including a dishwasher.

King Size Bed; Nectar mattress, light cotton blanket along with linens

Queen size Nectar mattress in master bedroom with walk-in closet and adjoining bathroom with large shower.

Cozy mood lighting to enjoy tropical nights and conversation with a cool drink or two.

Sun Haven House - 4 mi to beach! 2 beds/2 baths

2 bedrooms·2 baths

Sarasota • Florida

$ 4.040,59 USD totaal voor 30 nachten

18 nov – 18 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(4 reviews)

$ 10.481,85 USD $ 9.993,42 USD totaal voor 7 nachten

19–26 dec 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)

$ 2.178,64 USD totaal voor 7 nachten

28 nov – 5 dec 2026

Cozy Room 5 miles from beaches! image 1

Cozy Room 5 miles from beaches! image 2

Cozy Room 5 miles from beaches! image 3

Cozy Room 5 miles from beaches! image 4

Cozy Room 5 miles from beaches! image 5

Cozy Room 5 miles from beaches!

1 bedroom·1 bath

Sarasota • Florida

4.95(75 reviews)

$ 225,00 USD totaal voor 3 nachten

18–21 nov 2026

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 1

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 2

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 3

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 4

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 5

Lovely room 5 miles from Siesta Key w/ Pool & Spa!

1 bedroom·1 bath

Sarasota • Florida

4.87(60 reviews)

$ 225,00 USD totaal voor 3 nachten

1–4 dec 2026

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths

Sarasota • Florida

$150/ nacht(excl. kosten & belastingen)

The tiny home sits on a private 1.5 acre inland peninsula!

[Patio] Shared outdoor living space with fire pit

[Living area] This luxury 270sqft craftsman style tiny home is in the ideal location for your beach getaway.

Outdoor dining options available in the screened in lounge.

[Kitchen] Fully equipped kitchen featuring stainless steel appliances & gas cooktop. Coffee maker for all the coffee lovers out there!

·@Tiffanythetinyhome| island | netflix|bike|hammock

1 bedroom·1 bath

Sarasota • Florida

$ 452,00 USD totaal voor 3 nachten

18–21 nov 2026

[Living area] Smart TV with Netflix & Hulu

Waterfront tiny home sits on a private 1.5 acre inland peninsula! The perfect location for bird watching & kayaking around the lake.

[Living area] Doorway to the left leads into the main bedroom.

[Kitchen] Fully stocked & equipped kitchen with large farm sink and convection cooktop.

[Living area] French doors open up into the spacious backyard. Sofa converts into a bed for additional sleeping space.

@Shellmateisland |tiny home| island| bikes| kayaks

1 bedroom·1 bath

Sarasota • Florida

$ 574,00 USD totaal voor 3 nachten

18–21 nov 2026

Cozy coastal living with Smart TV & relaxing vibe

Lido Beach Pool & Pavilion, The 25-meter lap pool is open Friday through Sunday, from 10:00 am to 4:30 pm, weather permitting. Fees apply.

Primary queen suite with private ensuite and plenty of natural light

Sunny dining area for morning coffee or family dinners

Lido Key | Steps to Beach, Walk to St. Armands

2 bedrooms·2 baths

Sarasota • Florida

4.97(39 reviews)

$ 1.328,00 USD totaal voor 3 nachten

18–21 nov 2026