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

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

Palmetto House
Palmetto House
Palmetto House
Palmetto House
Palmetto House

Palmetto House

3 bedrooms·3 baths
Sarasota • Florida

$2,230.86 USD $2,036.45 USD total for 7 nights

Nov 9 – 16, 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

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

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

FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6
Your boutique Mediterranean-style 2BR bungalow (4 beds) — resort level comfort + coastal charm!
Your own private resort — located on a serene palm-lined lain in Sarasota’s coveted coastal district!
Half a mile to the Siesta Key, home of Siesta Key Beach — experience the sugar white sands of America’s #1 beach!
A Mediterranean-meets-California retreat where natural textures and curated details invite beautiful living

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath
Sarasota • Florida
5(2 reviews)

$2,248.70 USD total for 7 nights

Oct 24 – 31, 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

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)

$1,646.92 USD total for 5 nights

Oct 28 – Nov 2, 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4
Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths
Sarasota • Florida
5(2 reviews)

$10,632.14 USD $10,136.19 USD total for 7 nights

Dec 19 – 26, 2026

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 1
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 2
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 3
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 4
Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 5

Lovely room 5 miles from Siesta Key w/ Pool & Spa!

1 bedroom·1 bath
Sarasota • Florida
4.87(60 reviews)

$225.00 USD total for 3 nights

Nov 1 – 4, 2026

Cozy Room 5 miles from beaches! image 1
Cozy Room 5 miles from beaches! image 2
Cozy Room 5 miles from beaches! image 3
Cozy Room 5 miles from beaches! image 4
Cozy Room 5 miles from beaches! image 5

Cozy Room 5 miles from beaches!

1 bedroom·1 bath
Sarasota • Florida
4.95(75 reviews)

$225.00 USD total for 3 nights

Nov 1 – 4, 2026

Cozy coastal living with Smart TV & relaxing vibe
Lido Beach Pool & Pavilion, The 25-meter lap pool is open Friday through Sunday, from 10:00 am to 4:30 pm, weather permitting. Fees apply.
Primary queen suite with private ensuite and plenty of natural light
Lido Key Beach
Sunny dining area for morning coffee or family dinners

Lido Key | Steps to Beach, Walk to St. Armands

2 bedrooms·2 baths
Sarasota • Florida
4.97(39 reviews)
$310 – $696/ night(excl. fees & taxes)
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)
$278 – $580/ night(excl. fees & taxes)
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

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ night(excl. fees & taxes)
Welcome to your private paradise just minutes from the beach—where relaxation begins the moment you pull in.
Big group? No problem. Our extendable dining table fits up to 10—perfect for family feasts, card nights, or celebratory toasts.
Get the best of both worlds: soft and firm pillows, a private ensuite, blackout blinds for restful sleep, and a king bed made for unwinding. Plus, a smart TV for ultimate relaxation.
When the beach is a few blocks away but the pool is right here. Welcome to the best of both worlds.
Skip the restaurants (if you want to). This kitchen’s got everything: oven, microwave, fridge, dishwasher—even a TV so you don’t miss a moment.

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths
Siesta Key • Florida
5(36 reviews)

$3,696.54 USD total for 3 nights

Oct 20 – 23, 2026

Heated pool
Siesta Key beach
Dusk view of front of building
Front door and porch area
Front door and sliding glass doors

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath
Sarasota • Florida

$890.90 USD total for 3 nights

Oct 22 – 25, 2026

Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool
Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths
Siesta Key • Florida
5(26 reviews)

$14,950.00 USD total for 28 nights

Apr 15 – May 13, 2027

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

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 25 – 28, 2026

2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium
2 Bedroom/2 Bath, One Floor condominium

2 Bedroom/2 Bath, One Floor condominium

2 bedrooms·2 baths
Sarasota • Florida
$100/ night(excl. fees & taxes)
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches
Gulf Gate Escape near Siesta Key Beaches

Gulf Gate Escape near Siesta Key Beaches

2 bedrooms·2 baths
Sarasota • Florida

$722.00 USD total for 3 nights

Oct 25 – 28, 2026