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)
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 23, 2026 – Jan 21, 2027

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 23 – 26, 2026

View from front yard
Short walk to fishing pier
Fishing pier before hurricane Milton - now open but shorter than this photo.
Newly remodeled kitchen
Renovated Waterfront Home

Renovated Waterfront Home

3 bedrooms·2 baths
Osprey • Florida
4.4(5 reviews)

$1,394.40 USD total for 7 nights

Sep 23 – 30, 2026

Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!
Paradise at Seaplace on Longboat Key!

Paradise at Seaplace on Longboat Key!

2 bedrooms·2 baths
Longboat Key • Florida

$8,425.50 USD total for 60 nights

Sep 23 – Nov 22, 2026

Private pool
Dinning room and kitchen
Fully stocked kitchen
Full stocked kitchen
Full stocked kitchen

Tropical Escape Sarasota

3 bedrooms·2 baths
Sarasota • Florida

$2,130.00 USD total for 7 nights

Sep 23 – 30, 2026

Living room from hallway
Seasonal Golf-Course Townhome in The Meadows – Fully Furnished
Fully equipped kitchen opens on courtyard
Courtyard
Patio with golf view

Seasonal Golf-Course Townhome in The Meadows – Fully Furnished

3 bedrooms·2 baths
Sarasota • Florida
4(1 review)
$140 – $165/ night(excl. fees & taxes)
Welcome to The Beach, Unit 222!
The Beach complex from the waterfront - only 15 units, nice and quiet!
Pleasant!
View to the South - sit and stay a while!
Float the day away!

Condo with a View on Longboat Key

0 bedrooms·1 bath
Longboat Key • Florida
4.98(122 reviews)

$1,310.80 USD total for 3 nights

Sep 27 – 30, 2026

Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!
Ground Floor, Direct Oceanview on LBK!

Ground Floor, Direct Oceanview on LBK!

0 bedrooms·1 bath
Longboat Key • Florida
5(28 reviews)

$1,141.30 USD total for 3 nights

Sep 23 – 26, 2026

Welcome to The Beach on Longboat Key, Unit 224!
Warm and cozy!
Located mid-island, gulfside!
It's the good life.
White sand and turquoise waters!

Condo With a View 4: On the Beach!

1 bedroom·1 bath
Longboat Key • Florida
4.96(26 reviews)

$1,333.40 USD total for 3 nights

Sep 23 – 26, 2026

Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool
Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

3 bedrooms·2 baths
Sarasota • Florida
4.89(18 reviews)

$1,406.85 USD total for 3 nights

Sep 23 – 26, 2026

balcony + Gulf view
Living room with Gulf view
059-Unit 401-5
060-Unit 401-6
Beachfront Escape – Private Balcony, Gulf Views image 5

Panoramic Gulf View with Amazing Sunset.

1 bedroom·1 bath
Longboat Key • Florida
4.87(223 reviews)

$1,227.18 USD total for 3 nights

Sep 29 – Oct 2, 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1
052-Unit 64-2
059-Unit 64-9
058-Unit 64-8
060-Unit 64-10

Turtle Crawl Inn 64

1 bedroom·1 bath
Longboat Key • Florida
4.88(73 reviews)
$189 – $290/ night(excl. fees & taxes)
Right on the beach.Renovated ground Floor unit 63. image 1
020-Unit 63-4
023-Unit 63-7
024-Unit 63-8
Right on the beach.Renovated ground Floor unit 63. image 5

Turtle Crawl Inn 63

0 bedrooms·1 bath
Longboat Key • Florida
4.74(88 reviews)

$861.06 USD total for 3 nights

Sep 24 – 27, 2026

IMG Academy, Heated Pool, Huge Game Room & Golf! image 1
IMG Academy, Heated Pool, Huge Game Room & Golf! image 2
IMG Academy, Heated Pool, Huge Game Room & Golf! image 3
IMG Academy, Heated Pool, Huge Game Room & Golf! image 4
IMG Academy, Heated Pool, Huge Game Room & Golf! image 5

Sunny Bradenton Oasis, Pool/ Near Beaches & Golf!

4 bedrooms·2 baths
Bradenton • Florida

$853.15 USD $821.80 USD total for 3 nights

Sep 28 – Oct 1, 2026

Casa Milly image 1
Casa Milly image 2
Casa Milly image 3
Casa Milly image 4
Casa Milly image 5

Casa Milly

2 bedrooms·1 bath
Bradenton • Florida
5(36 reviews)
$150/ night(excl. fees & taxes)
Just at the bottom of the stairs! The beach awaits...!
Welcome to Silver Sands, Unit 256 on Longboat Key!
We're right on the Gulf! No need to cross a busy street to get to the beach!
A bird's eye view!
Silver Sands Gulf Beach Resort -- iconic, well-known (and loved!), old Florida charm, located on Gulf of Mexico Dr., beach side, just 35 units!

Tropical Beach Condo!

1 bedroom·1 bath
Longboat Key • Florida
5(11 reviews)

$1,153.60 USD total for 3 nights

Oct 16 – 19, 2026

Our home is in the left side of the picture.
The front of our home.
Sunset View
Established 2019
Entry

Craig House with Heated Pool

3 bedrooms·2 baths
Bradenton • Florida
4.8(107 reviews)

$1,150.60 USD $1,104.12 USD total for 5 nights

Oct 6 – 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)
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater
Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths
Bradenton • Florida

$6,002.88 USD total for 3 nights

Sep 23 – 26, 2026

Backyard Oasis: Dive into relaxation with a sparkling pool and spa, surrounded by lush greenery!
Exterior: Vibrant sunsets and lush greenery await you in this stunning Bradenton retreat!
Living room with leather sofa, chairs and coffee table
Fully equipped kitchen with stainless steel appliances including French Door refrigerator with water and ice maker in door, glass electric stove, oven, microwave, coffee maker, electric tea kettle, dishes, cooking and baking pans, pots
Wood dining table

Heated Pool, Spa, BBQ, Games, Fire Pit, Sleeps 10

3 bedrooms·2 baths
Bradenton • Florida
5(75 reviews)
$109 – $756/ night(excl. fees & taxes)
Close to beautiful Venice Beach
Close to beautiful Venice Beach
Close to beautiful Venice Beach
Close to beautiful Venice Beach
Close to beautiful Venice Beach

Close to beautiful Venice Beach

1 bedroom·1 bath
Venice • Florida

$240.00 USD total for 3 nights

Sep 23 – 26, 2026

Perfect place to relax, read a book, and cool down with a dip in crystal clear pool with water fall feature
Sun Soaked Paradise - Heated Pool image 2
Front of house
Front entry way
Sun Soaked Paradise - Heated Pool image 5

Sun Soaked Paradise - Heated Pool

3 bedrooms·2 baths
Bradenton • Florida
$225 – $245/ night(excl. fees & taxes)
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views
Golf Course and Private Pool Views

Golf Course and Private Pool Views

2 bedrooms·2 baths
Manatee County • Florida

$13,700.00 USD total for 60 nights

Sep 23 – Nov 22, 2026