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

Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key
Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

2 bedrooms·2 baths
Longboat Key • Florida

$25,878.00 USD total for 120 nights

Sep 23, 2026 – Jan 21, 2027

Golf Course Condo
Golf Course Condo
Golf Course Condo
Golf Course Condo
Golf Course Condo

Golf Course Condo

2 bedrooms·2 baths
Sarasota • Florida

$3,665.00 USD total for 30 nights

Sep 23 – Oct 23, 2026

Screened in patio, table with seating for 8 and 2 bedrooms look out onto pool as well as the main living space.
Well maintained exterior with new roof and hurricane windows.
Master Bedroom, King bed with french doors to pool and screened in patio
Master Bedroom, King bed, ceiling fan and bedside lamps touch control with USB ports.
Master Bath walk in shower

3BR/2B Vacation Pool Home, Nokomis Fl Rental

3 bedrooms·2 baths
Nokomis • Florida
5(3 reviews)

$2,052.50 USD $1,872.25 USD total for 7 nights

Sep 23 – 30, 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 23 – Dec 22, 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

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

6 bedrooms·4 baths
Bradenton • Florida

$2,297.12 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

Welcome to Paradise
Welcome to Paradise
Welcome to Paradise
Welcome to Paradise
Welcome to Paradise

Welcome to Paradise

3 bedrooms·2 baths
Bradenton • Florida

$718.65 USD total for 3 nights

Sep 23 – 26, 2026

Gulf Access
Gulf Access
Gulf Access
Gulf Access
Gulf Access

Gulf Access

4 bedrooms·4½ baths
Longboat Key • Florida

$60,500.00 USD total for 30 nights

Sep 23 – Oct 23, 2026

Sitting Area w/fireplace and desk
Floorplan layout
Workspace w/2GB Fiber Internet
Full kitchen w/new appliances
Coffee Bar w/K-cups, tea, sugar

Bradenton Boho Bungalow

3 bedrooms·2 baths
Bradenton • Florida

$1,008.00 USD total for 3 nights

Sep 23 – 26, 2026

Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway
Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths
Bradenton • Florida

$1,502.00 USD total for 3 nights

Sep 29 – Oct 2, 2026