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

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ night(excl. fees & taxes)
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)
$446 – $860/ 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

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 total for 3 nights

Sep 7 – 10, 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

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)
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)

$1,673.69 USD total for 5 nights

Sep 10 – 15, 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/ night(excl. fees & taxes)
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 total for 3 nights

Sep 7 – 10, 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 total for 7 nights

Oct 24 – 31, 2026

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 total for 3 nights

Sep 7 – 10, 2026

Simple Old Florida Style Home image 1
Simple Old Florida Style Home image 2
Simple Old Florida Style Home image 3
Simple Old Florida Style Home image 4
Simple Old Florida Style Home image 5

Bring your motorboat:Simple Old Florida Style Home

2 bedrooms·2 baths
Englewood • Florida

$405.57 USD total for 4 nights

Sep 7 – 11, 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)
$312 – $1,812/ night(excl. fees & taxes)
Palmetto House
Palmetto House
Palmetto House
Palmetto House
Palmetto House

Palmetto House

3 bedrooms·3 baths
Sarasota • Florida
$193 – $557/ night(excl. fees & taxes)
Sarasota vacation rental
Sarasota vacation rental
Sarasota vacation rental
Sarasota vacation rental
Sarasota vacation rental

Sarasota vacation rental

3 bedrooms·2 baths
Sarasota • Florida

$500.00 USD total for 3 nights

Sep 7 – 10, 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 total for 3 nights

Sep 7 – 10, 2026

Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month
Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

2 bedrooms·2 baths
Sarasota • Florida

$31,480.00 USD total for 120 nights

Sep 7, 2026 – Jan 5, 2027

Master king bedroom with en suite bathroom
Home with hot tub, 5 miles to Englewood beach image 2
Home with hot tub, 5 miles to Englewood beach image 3
Home with hot tub, 5 miles to Englewood beach image 4
Home with hot tub, 5 miles to Englewood beach image 5

Home with hot tub, 5 miles to Englewood beach

2 bedrooms·2 baths
Englewood • Florida
4.98(54 reviews)
$80 – $149/ night(excl. fees & taxes)