Main living room with ample seating, dining today and bright sunshine gracing the windows.
Move the additional seating over to the couch after sitting down for dinner.
Lido Key Beach
Dinner for 4. Quick and easy access to the full size kitchen for home cooked meals while on vacay.
Queen bed, with additional ceiling fans if you like it really cold and of course your very own private full bathroom. Also, ample closet space to fully stretch out.

Lido Key Beach Escape | 2 Private Suites

2 bedrooms·2 baths
Sarasota • Florida
4.95(21 reviews)
$243 – $580/ night(excl. fees & taxes)
Palmetto House
Palmetto House
Palmetto House
Palmetto House
Palmetto House

Palmetto House

3 bedrooms·3 baths
Sarasota • Florida
$215 – $557/ 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 23 – 30, 2026

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

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

Exterior
Kings Gate Mobile Home
Kings Gate Mobile Home
Kings Gate Mobile Home
Kings Gate Mobile Home

Kings Gate Mobile Home

1 bedroom·1 bath
Nokomis • Florida

$3,275.00 USD total for 30 nights

Sep 23 – Oct 23, 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

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)