7th-Floor Water-View Getaway on Siesta Key
7th-Floor Water-View Getaway on Siesta Key
7th-Floor Water-View Getaway on Siesta Key
7th-Floor Water-View Getaway on Siesta Key
7th-Floor Water-View Getaway on Siesta Key

7th-Floor Water-View Getaway on Siesta Key

1 bedroom·1 bath
Siesta Key • Florida

$1,318.00 USD total for 7 nights

Oct 26 – Nov 2, 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

Oct 20, 2026 – Feb 17, 2027

Heated pool & spa
Bathroom 1 bath/shower
Bathroom 2 walk in shower
Bedroom 1
Bedroom 3

Heated Pool & Spa 3bd/2bth, near Siesta Key Beach

3 bedrooms·2 baths
Sarasota • Florida

$600.00 USD total for 3 nights

Oct 20 – 23, 2026

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

Oct 20 – 23, 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

Oct 20 – 27, 2026

La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 1
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 2
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 3
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 4
La Quinta Sarasota 2 Double | Breakfast, Gym&Pool image 5

La Quinta Sarasota 2 Double | Breakfast, Gym&Pool

1 bedroom·1 bath
Sarasota • Florida

$292.67 USD total for 3 nights

Oct 20 – 23, 2026

La Quinta Sarasota King Std | Breakfast, Gym&Pool image 1
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 2
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 3
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 4
La Quinta Sarasota King Std | Breakfast, Gym&Pool image 5

La Quinta Sarasota King Std | Breakfast, Gym&Pool

1 bedroom·1 bath
Sarasota • Florida

$262.16 USD total for 3 nights

Oct 20 – 23, 2026

Private screened salt water pool
Sundays on Putnam | Private Heated Pool
Sundays on Putnam | Private Heated Pool
Bright designer kitchen with farmhouse sink, chic pink fridge, and a gas stove.
Sundays on Putnam | Private Heated Pool

Sundays on Putnam | Private Heated Pool

2 bedrooms·2½ baths
Sarasota • Florida

$1,596.00 USD total for 7 nights

Oct 20 – 27, 2026

Osprey Harbor Village 216
Osprey Harbor Village 216
Osprey Harbor Village 216
Osprey Harbor Village 216
Osprey Harbor Village 216

Osprey Harbor Village 216

3 bedrooms·2 baths
Osprey • Florida

$8,340.00 USD total for 30 nights

Oct 20 – Nov 19, 2026

Property grounds
Terrace/patio
Bathroom
Bathroom
Bathroom

Beautiful 2 Bed/2 Bath Cozy Cottage Retreat — Your Home Away From Home

1 bedroom·1 bath
Sarasota • Florida

$713.00 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – Dec 19, 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

Oct 20 – 27, 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)

$14,362.15 USD total for 75 nights

Jan 2 – Mar 18, 2027

Float the day away!
View from our lanai - straight on out!
The sweet life!
Nice and airy!
Relax!

Condo with a View on Longboat Key

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

$971.80 USD total for 3 nights

Oct 21 – 24, 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)

$971.80 USD total for 3 nights

Oct 20 – 23, 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

Oct 20 – 23, 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

Nov 16 – 19, 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)

$932.25 USD total for 3 nights

Oct 26 – 29, 2026

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)

$815.86 USD total for 3 nights

Oct 27 – 30, 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

Oct 20, 2026 – Feb 17, 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

Oct 20 – Nov 19, 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

Oct 20 – 27, 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

Oct 20 – Nov 19, 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

$914.17 USD $879.76 USD total for 3 nights

Nov 8 – 11, 2026