Relax in the spacious living room while enjoying breathtaking Gulf views through floor-to-ceiling sliding glass doors leading out to the screened/glassed lanai
Spacious living room with comfortable leather seating, a large smart TV, and direct access to the screened/glassed lanai.
Beautifully updated gourmet kitchen featuring granite countertops, stainless steel appliances, and plenty of room to prepare meals.
Designed with extended stays in mind, this spacious kitchen offers abundant cabinetry and generous workspace.
The open dining area comfortably seats six and flows seamlessly into the beautifully updated kitchen.

Gulf Front on Siesta Key - Fishermans Haven 403

2 bedrooms·2 baths
Sarasota • Florida
$133 – $239/ night(excl. fees & taxes)
Located directly on the beach! Morning coffee on the lanai overlooking Gulf and beach!
New living room furniture with views!
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo
Siesta Key Beachfront Condo

Siesta Key Beachfront Condo

2 bedrooms·2 baths
Siesta Key • Florida

$3,113.26 USD total for 7 nights

Sep 19 – 26, 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

$463.00 USD total for 3 nights

Sep 7 – 10, 2026

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

$376.00 USD total for 3 nights

Sep 7 – 10, 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 total for 3 nights

Sep 7 – 10, 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 total for 30 nights

Sep 7 – Oct 7, 2026

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ night(excl. fees & taxes)
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 total for 3 nights

Sep 7 – 10, 2026

506 Siesta
506 Siesta
506 Siesta
506 Siesta
506 Siesta

506 Siesta

2 bedrooms·2 baths
Sarasota • Florida
$235/ night(excl. fees & taxes)
Private beach access is 350 steps from property gate
Incredible Pool
Gated access and covered parking
Brand new furnishings make this feel like a retreat
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 total for 5 nights

Sep 12 – 17, 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
$171 – $325/ night(excl. fees & taxes)
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)

$2,175.85 USD total for 5 nights

Sep 7 – 12, 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 total for 30 nights

Sep 7 – Oct 7, 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 total for 7 nights

Sep 7 – 14, 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/ night(excl. fees & taxes)
Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side
Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side
Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side
Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side
Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

2 bedrooms·2 baths
Siesta Key • Florida
Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard
Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard
Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard
Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard
Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard

Casa mar - Unit 62 ; 1 Bedroom 1 Bath Courtyard

1 bedroom·1 bath
Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 17 1 Bedroom 1 Bath
Casa Mar - Unit 17 1 Bedroom 1 Bath
Casa Mar - Unit 17 1 Bedroom 1 Bath
Casa Mar - Unit 17 1 Bedroom 1 Bath
Casa Mar - Unit 17 1 Bedroom 1 Bath

Casa Mar - Unit 17 1 Bedroom 1 Bath

1 bedroom·1 bath
Siesta Key • Florida

$3,660.80 USD total for 14 nights

Oct 2 – 16, 2026

Free cancellation
Casa Mar - Unit 4 1 Bedroom 1 Bath
Casa Mar - Unit 4 1 Bedroom 1 Bath
Casa Mar - Unit 4 1 Bedroom 1 Bath
Casa Mar - Unit 4 1 Bedroom 1 Bath
Casa Mar - Unit 4 1 Bedroom 1 Bath

Casa Mar - Unit 4 1 Bedroom 1 Bath

1 bedroom·1 bath
Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 12A 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath
Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath
Casa Mar - Unit 25 1 Bedroom 1 Bath

Casa Mar - Unit 25 1 Bedroom 1 Bath

1 bedroom·1 bath
Siesta Key • Florida

$1,930.40 USD total for 7 nights

Sep 15 – 22, 2026

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 26 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath
Siesta Key • Florida

$941.60 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 27 Studio Pool View
Casa Mar - Unit 27 Studio Pool View
Casa Mar - Unit 27 Studio Pool View
Casa Mar - Unit 27 Studio Pool View
Casa Mar - Unit 27 Studio Pool View

Casa Mar - Unit 27 Studio Pool View

0 bedrooms·1 bath
Siesta Key • Florida

$765.40 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

2 bedrooms·2 baths
Siesta Key • Florida

$1,254.40 USD total for 3 nights

Sep 19 – 22, 2026