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)

$2,384.30 USD total for 7 nights

Oct 24 – 31, 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)
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)
$525/ night(excl. fees & taxes)
Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 1
Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 2
Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 3
Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 4
Sunny Bradenton Double Queen: Breakfast, Pool &Gym image 5

Sunny Bradenton Double Queen: Breakfast, Pool &Gym

1 bedroom·1 bath
Bradenton • Florida

$586.50 USD total for 3 nights

Sep 7 – 10, 2026

Sunny Bradenton King Studio: Breakfast, Pool & Gym image 1
Sunny Bradenton King Studio: Breakfast, Pool & Gym image 2
Sunny Bradenton King Studio: Breakfast, Pool & Gym image 3
Sunny Bradenton King Studio: Breakfast, Pool & Gym image 4
Sunny Bradenton King Studio: Breakfast, Pool & Gym image 5

Sunny Bradenton King Studio: Breakfast, Pool & Gym

1 bedroom·1 bath
Bradenton • Florida

$586.50 USD total for 3 nights

Sep 7 – 10, 2026

Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches
Waterfront Home with Heated Pool 2 Mi from Beaches

Waterfront Home with Heated Pool 2 Mi from Beaches

3 bedrooms·2 baths
St. Petersburg • Florida
4.9(51 reviews)

$1,497.00 USD total for 3 nights

Sep 7 – 10, 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)

$1,673.69 USD total for 5 nights

Sep 10 – 15, 2026

Paddle boarding just off the dock around mangroves.
Waterfront yard with dock for fishing and launching paddle boards and kayaks and turf for chilling
Mangrove Haven
Mangrove Haven
Mangrove Haven

Mangrove Haven

3 bedrooms·3 baths
St. Petersburg • Florida
$388 – $1,619/ night(excl. fees & taxes)
Even Hotel, Sarasota, FL Double Studio image 1
Even Hotel, Sarasota, FL Double Studio image 2
Even Hotel, Sarasota, FL Double Studio image 3
Even Hotel, Sarasota, FL Double Studio image 4
Even Hotel, Sarasota, FL Double Studio image 5

Even Hotel, Sarasota, FL Double Studio

1 bedroom·1 bath
Sarasota • Florida

$494.94 USD total for 3 nights

Sep 7 – 10, 2026

Even Hotel, Sarasota, FL King Studio image 1
Even Hotel, Sarasota, FL King Studio image 2
Even Hotel, Sarasota, FL King Studio image 3
Even Hotel, Sarasota, FL King Studio image 4
Even Hotel, Sarasota, FL King Studio image 5

Even Hotel, Sarasota, FL King Studio

1 bedroom·1 bath
Sarasota • Florida

$494.94 USD total for 3 nights

Sep 7 – 10, 2026

Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!

Funshine Sunset Beach - Steps from the beach!!

1 bedroom·1 bath
Treasure Island • Florida
5(142 reviews)

$499.08 USD $279.35 USD total for 3 nights

Sep 13 – 16, 2026

Private pool deck with lounge chairs, pool noodles, and floats included. Fully fenced, tropical landscaping, sleeps 10. Gulfport/South St. Pete, FL.
Primary king suite — palm-leaf mural, neon accent, woven pendant lights, and barn door entry to private spa ensuite. St. Petersburg, FL vacation rental.
Open-plan living and kitchen — 65-inch smart TV, breakfast bar with 4 stools, and mustard yellow sofas. 4-bedroom vacation rental, St. Petersburg, FL.
The Disco Lounge at Tropical Disco — retro-inspired gathering space with coral sectional, palm-print ceiling, multiple disco balls, and neon signs. St. Pete, FL.
Spa-like ensuite — dual marble vanity, backlit mirror, palm-leaf mural walls, and oversized walk-in rain shower. St. Pete, FL pool home.

Tropical Disco | Pool & Fire Pit | St. Pete Beach

4 bedrooms·2 baths
Gulfport • Florida
5(179 reviews)
$179 – $787/ night(excl. fees & taxes)
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

Sep 8 – 11, 2026

Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

3 bedrooms·1 bath
St. Petersburg • Florida
4.63(19 reviews)

$3,949.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

1 bedroom·1 bath
St. Petersburg • Florida
4.46(13 reviews)

$625.00 USD total for 7 nights

Sep 7 – 14, 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

Sep 7 – 10, 2026

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

2 bedrooms·1 bath
St. Petersburg • Florida
5(4 reviews)

$750.00 USD total for 5 nights

Sep 7 – 12, 2026

you never have to cover the windows, it's a private yard.
Pool view from the dining area
TOP WORLD BEACH AND #1 US BEACH
my favorite yellow lifeguard shack. LET'S GO VISIT>>>>> Are you coming????
Dining Room

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths
Siesta Key • Florida
4.64(58 reviews)

$2,062.25 USD total for 7 nights

Sep 12 – 19, 2026

The Downtown Dali House City of St. Petersburg image 1
The Downtown Dali House City of St. Petersburg image 2
The Downtown Dali House City of St. Petersburg image 3
The Downtown Dali House City of St. Petersburg image 4
The Downtown Dali House City of St. Petersburg image 5

The Downtown Dali House City of St. Petersburg

3 bedrooms·2 baths
St. Petersburg • Florida
4.86(7 reviews)

$1,190.00 USD total for 3 nights

Sep 7 – 10, 2026

cozy living room
modern kitchen
modern bedroom
coffee station
front door

Seashell Studio sanctuary by the sea

1 bedroom·1 bath
St. Petersburg • Florida

$405.00 USD total for 3 nights

Sep 7 – 10, 2026

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

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths
Siesta Key • Florida
5(2 reviews)
$446 – $860/ night(excl. fees & taxes)
Treasure Island Waterfront Luxury Condo image 5
Treasure Island Waterfront Luxury Condo image 1
Treasure Island Waterfront Luxury Condo image 2
Treasure Island Waterfront Luxury Condo image 3
Treasure Island Waterfront Luxury Condo image 4

Treasure Island Waterfront Luxury Condo

2 bedrooms·2 baths
Treasure Island • Florida
5(3 reviews)

$1,605.00 USD total for 5 nights

Sep 12 – 17, 2026

Relaxed lounge area, kick back, stream, and recharge.
Open living space designed for comfort, light, and flow.
Inviting dining space with subtle coastal tones for shared meals and relaxed evenings.
Fully equipped kitchen, perfect for easy meals or longer stays.
Modern kitchen with clean lines and coastal-inspired finishes.

The Indigo Escape

2 bedrooms·2 baths
Sarasota • Florida

$6,757.67 USD total for 14 nights

Sep 7 – 21, 2026

The Sapphire Escape
The Sapphire Escape
The Sapphire Escape
The Sapphire Escape
The Sapphire Escape

The Sapphire Escape

1 bedroom·1 bath
Sarasota • Florida

$2,053.91 USD total for 14 nights

Sep 7 – 21, 2026