Our Private Beach with chairs and umbrellas all included!!
Just a day at our private beach
Sandy's Siesta Key Condo
Sandy's Siesta Key Condo
Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

2 bedrooms·1½ baths
Sarasota County • Florida

$1,200.01 USD total for 7 nights

Nov 8 – 15, 2026

Back yard with new pool 15x28 ft
Pool Depth 3ft-5ft
Casa Blanca Ranch Home near Siesta Key Beach
15x28 ft pool with spa/hot tub
New Sun Shelves with pool chaises

Casa Blanca Ranch Home near Siesta Key Beach

3 bedrooms·2 baths
Sarasota • Florida
5(18 reviews)

$2,220.25 USD total for 5 nights

Sep 29 – Oct 4, 2026

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)

$1,683.00 USD total for 5 nights

Oct 28 – Nov 2, 2026

Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches
Gulf Gate Paradise near Siesta Key beaches

Gulf Gate Paradise near Siesta Key beaches

1 bedroom·1 bath
Sarasota • Florida
5(71 reviews)

$427.00 USD total for 3 nights

Oct 8 – 11, 2026

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ 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 29 – Oct 6, 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 29 – Nov 28, 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

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

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

Sep 29 – Oct 2, 2026

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

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 29 – Nov 28, 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 29 – Oct 2, 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

Tropical Mediterranean Villa
Tropical Lanai Salt Water Pool - Jacuzzi
Cathedral Great Room
California King
Modern Kitchen

Villa Ocala

3 bedrooms·2 baths
Venice • Florida

$1,378.60 USD $1,322.38 USD total for 5 nights

Sep 29 – Oct 4, 2026

Aerial shot of house and pool.
Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub
Aerial of patio & pool
Pool & outdoor area at night.
Pool & Hot tub at night.

Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 bedrooms·2 baths
Bradenton • Florida
5(50 reviews)

$1,880.00 USD total for 3 nights

Dec 25 – 28, 2026

View of condo from Sarasota Bay.
View of complex from public beach/Coquina Beach
Community pool
Sunrise over Sarasota Bay from condo decks/bedroom/living room
Sunset of the Gulf from condo and public beach/Coquina Beach

Sunrise/Sunset

2 bedrooms·2 baths
Bradenton Beach • Florida

$2,815.25 USD total for 7 nights

Sep 29 – Oct 6, 2026

My Peaceful place on the bay. image 1
My Peaceful place on the bay. image 2
My Peaceful place on the bay. image 3
My Peaceful place on the bay. image 4
My Peaceful place on the bay. image 5

My Peaceful place on the bay.

2 bedrooms·2 baths
Bradenton • Florida
4.99(187 reviews)

$549.49 USD total for 3 nights

Oct 24 – 27, 2026

Family home on Golf Course image 1
Family home on Golf Course image 2
Pool
Family home on Golf Course image 4
Family home on Golf Course image 5

Family home on Golf Course

4 bedrooms·4 baths
Bradenton • Florida

$2,550.00 USD total for 5 nights

Oct 1 – 6, 2026

Dive into your own private paradise! Welcome to your "Happy Place" with a private fully-fenced backyard, surrounded by mature palm trees and a spacious HEATED SALTWATER POOL, plus tons of color changing lights!
Covered patio with fire pit, dining area & BBQ—perfect evenings
The sunlit Family Room with sparkling swimming pool views, an expansive L-shaped couch, oversized ottoman, children's books, games, and Smart TV for endless entertainment options, make it the perfect hub for relaxation and family fun!
Screened pool oasis with loungers, travertine deck & sunset views
Stainless LG appliances Quartz countertops Child & baby-friendly amenities Fully Stocked

Heated Pool+5mile to AMI & IMG+Kid Friendly

4 bedrooms·2 baths
Bradenton • Florida
5(114 reviews)

$1,565.29 USD total for 4 nights

Oct 21 – 25, 2026

350 feet of waterfront and a pair that extended out 250 feet into the river.
The house all lite up at night. Very peaceful
The Blue Heron Riverfront Retreat
The Blue Heron Riverfront Retreat
The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

4 bedrooms·4 baths
Ellenton • Florida
5(3 reviews)

$3,735.88 USD total for 5 nights

Oct 11 – 16, 2026

32” TV with streaming device Comfortable couch.
Kitchen, diningroom, livingroom area
Gulf Coast Paradise Hideaway
Queen bed, night stand with usb plug, and lamp. 32”TV with streaming device sits on top of Armoire with plenty of storage. Bedroom does have closet with hangers.
Gulf Coast Paradise Hideaway

Gulf Coast Paradise Hideaway

1 bedroom·1 bath
Palmetto • Florida

$989.85 USD $911.32 USD total for 7 nights

Sep 29 – Oct 6, 2026

beautiful pool area - facing south west
Welcome to Villa Happy Gator
Your favorite place for a sunbath
large open space welcomes you
entertainment

Florida Pool Villa Happy Gator

3 bedrooms·2 baths
Venice • Florida
5(102 reviews)

$1,689.35 USD $1,616.18 USD total for 7 nights

Oct 27 – Nov 3, 2026