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

Casa Mar Unit 34 | 2BR Steps to Beach
Casa Mar Unit 34 | 2BR Steps to Beach
Casa Mar Unit 34 | 2BR Steps to Beach
Casa Mar Unit 34 | 2BR Steps to Beach
Casa Mar Unit 34 | 2BR Steps to Beach

Casa Mar Unit 34 | 2BR Steps to Beach

2 bedrooms·2 baths
Siesta Key • Florida

$1,254.40 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 35 ; 2 Bedroom 2 Bath Beach Front

2 bedrooms·2 baths
Siesta Key • Florida

$1,560.40 USD total for 3 nights

Sep 15 – 18, 2026

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

2 bedrooms·2 baths
Siesta Key • Florida

$1,560.40 USD total for 3 nights

Sep 12 – 15, 2026

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front
Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

Casa Mar - Unit 41 ; 2 Bedroom 2 Bath Beach Front

2 bedrooms·2 baths
Siesta Key • Florida

$1,560.40 USD total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 45 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 45 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 45 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 45 ; 2 Bedroom 1.5 Bath Pool View
Casa Mar - Unit 45 ; 2 Bedroom 1.5 Bath Pool View

Casa Mar - Unit 45 ; 2 Bedroom 1.5 Bath Pool View

2 bedrooms·2 baths
Siesta Key • Florida
Casa Mar - Unit 43 ; 2 Bdrm Close to Beach
Casa Mar - Unit 43 ; 2 Bdrm Close to Beach
Casa Mar - Unit 43 ; 2 Bdrm Close to Beach
Casa Mar - Unit 43 ; 2 Bdrm Close to Beach
Casa Mar - Unit 43 ; 2 Bdrm Close to Beach

Casa Mar - Unit 43 ; 2 Bdrm Close to Beach

2 bedrooms·2 baths
Siesta Key • Florida

$1,254.40 USD total for 3 nights

Sep 19 – 22, 2026

Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View
Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View
Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View
Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View
Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View

Casa Mar - Unit 46 ; 2 Bedroom 1 Bath Pool View

2 bedrooms·1 bath
Siesta Key • Florida
$242 – $388/ night(excl. fees & taxes)
Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View
Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View

Casa Mar - Unit 51 ; 1 Bedroom 1 Bath Pool View

1 bedroom·1 bath
Siesta Key • Florida

$941.60 USD $756.21 USD total for 3 nights

Sep 8 – 11, 2026

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 total for 3 nights

Sep 7 – 10, 2026

Casa Mar - Unit 67 Studio Pool View
Casa Mar - Unit 67 Studio Pool View
Casa Mar - Unit 67 Studio Pool View
Casa Mar - Unit 67 Studio Pool View
Casa Mar - Unit 67 Studio Pool View

Casa Mar - Unit 67 Studio Pool View

0 bedrooms·1 bath
Siesta Key • Florida
$142 – $251/ night(excl. fees & taxes)
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 total for 3 nights

Sep 7 – 10, 2026

Casa mar - Unit 74
Casa mar - Unit 74
Casa mar - Unit 74
Casa mar - Unit 74
Casa mar - Unit 74

Casa mar - Unit 74

1 bedroom·1 bath
Siesta Key • Florida

$873.20 USD total for 3 nights

Sep 7 – 10, 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)
The Sapphire Escape
The Sapphire Escape
The Sapphire Escape
The Sapphire Escape
The Sapphire Escape

The Sapphire Escape

1 bedroom·1 bath
Sarasota • Florida

$2,053.91 USD total for 14 nights

Sep 7 – 21, 2026

Relaxed lounge area, kick back, stream, and recharge.
Open living space designed for comfort, light, and flow.
Inviting dining space with subtle coastal tones for shared meals and relaxed evenings.
Fully equipped kitchen, perfect for easy meals or longer stays.
Modern kitchen with clean lines and coastal-inspired finishes.

The Indigo Escape

2 bedrooms·2 baths
Sarasota • Florida

$6,757.67 USD total for 14 nights

Sep 7 – 21, 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths
Siesta Key • Florida
5(2 reviews)
$290 – $860/ night(excl. fees & taxes)
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ night(excl. fees & taxes)
you never have to cover the windows, it's a private yard.
Pool view from the dining area
TOP WORLD BEACH AND #1 US BEACH
my favorite yellow lifeguard shack. LET'S GO VISIT>>>>> Are you coming????
Dining Room

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths
Siesta Key • Florida
4.64(58 reviews)

$2,062.25 USD total for 7 nights

Sep 12 – 19, 2026

Carriage homes, four to a building. Ours is bottom right with light blue car in driveway/garage area.
Enjoy fishing or kayaking from our lakes, this lake is connected to four other lakes accessible via kayak.
Spacious living room with Smart TV and the VIEW!!!
Living room
Private ground floor patio/lanai.

Resort Living Turnkey Carriage Home, waterfront

2 bedrooms·2 baths
Venice • Florida

$7,400.00 USD total for 90 nights

Sep 7 – Dec 6, 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 total for 3 nights

Sep 7 – 10, 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 total for 3 nights

Sep 8 – 11, 2026

Beautiful Resort-Style Gran Paradiso Townhouse
Hot Tub
Gran Paradiso Community
Community Pool
Sports Courts

Beautiful Resort-Style Gran Paradiso Townhouse

3 bedrooms·2½ baths
Venice • Florida
$150/ night(excl. fees & taxes)
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)
$525/ night(excl. fees & taxes)