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Vacation rentals in Siesta Key, Florida, United States

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

1 bedroom·1 bath

Siesta Key • Florida

$ 941,60 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

Casa Mar - Unit 73 ; Courtyard 1 Bedroom 1 Bath

1 bedroom·1 bath

Siesta Key • Florida

$ 873,20 USD totaal voor 3 nachten

29 sep – 2 okt 2026

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 bedrooms·2 baths

Sarasota • Florida

$100/ nacht(excl. kosten & belastingen)

Welcome to your private paradise just minutes from the beach—where relaxation begins the moment you pull in.

Big group? No problem. Our extendable dining table fits up to 10—perfect for family feasts, card nights, or celebratory toasts.

Get the best of both worlds: soft and firm pillows, a private ensuite, blackout blinds for restful sleep, and a king bed made for unwinding. Plus, a smart TV for ultimate relaxation.

When the beach is a few blocks away but the pool is right here. Welcome to the best of both worlds.

Skip the restaurants (if you want to). This kitchen’s got everything: oven, microwave, fridge, dishwasher—even a TV so you don’t miss a moment.

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths

Siesta Key • Florida

5(36 reviews)

$ 3.297,65 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Siesta Dunes Pool

Living room - 65" TV, sleeper sofa

Lanai with sliders - "Palm View"

Living room - 65" TV, sleeper sofa

Living room with 65" TV

Palm View at Siesta Dunes

2 bedrooms·2 baths

Siesta Key • Florida

5(15 reviews)

$ 2.580,08 USD totaal voor 7 nachten

23–30 okt 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

29 sep – 29 okt 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

8–15 nov 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

7–12 okt 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)

$ 2.220,25 USD totaal voor 5 nachten

29 sep – 4 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

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

8–11 okt 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

29 sep – 29 okt 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)

$ 1.683,00 USD totaal voor 5 nachten

28 okt – 2 nov 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

8–11 okt 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)

$ 10.632,14 USD $ 10.136,19 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)

$ 2.384,30 USD totaal voor 7 nachten

24–31 okt 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

29 sep – 2 okt 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

4–7 okt 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

$ 436,00 USD totaal voor 3 nachten

29 sep – 2 okt 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

$ 553,00 USD totaal voor 3 nachten

29 sep – 2 okt 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)

$ 1.100,00 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Main living room with ample seating, dining today and bright sunshine gracing the windows.

Move the additional seating over to the couch after sitting down for dinner.

Dinner for 4. Quick and easy access to the full size kitchen for home cooked meals while on vacay.

Queen bed, with additional ceiling fans if you like it really cold and of course your very own private full bathroom. Also, ample closet space to fully stretch out.

Lido Key Beach Escape | 2 Private Suites

2 bedrooms·2 baths

Sarasota • Florida

4.95(21 reviews)

$ 1.143,87 USD totaal voor 3 nachten

29 sep – 2 okt 2026