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 26 – 29, 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 23 – 26, 2026

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

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa
Fun in the sun starts here - Hosted by RentAnnaMaria
Sunset Views from Shore to Please! - Hosted by RentAnnaMaria
Shore to Please - Hosted by RentAnnaMaria
Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths
Anna Maria • Florida
5(13 reviews)

$3,059.78 USD total for 4 nights

Nov 8 – 12, 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 23 – Dec 22, 2026

Bright bath w/ clean design & practical comfort.
Luxurious outdoor sauna surrounded by lush tropical greenery.
Sunset-lit pool perfect for unwinding year-round
Spa-like bath w/ stone accents for soothing moments.
Cozy guest room offering calm, sunny comfort.

Luxury Pool Home in Riverview Tampa

4 bedrooms·2½ baths
Riverview • Florida
5(25 reviews)

$1,350.90 USD total for 3 nights

Oct 26 – 29, 2026

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater
Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

Sleeps 25 • Heated Pool • Indoor/Outdoor Games• Theater

7 bedrooms·4 baths
Tampa • Florida

$4,250.40 USD total for 3 nights

Oct 23 – 26, 2026

Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Front of house.
Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach
Beautiful day at the beach

Oceanview Gulf-Front 2BR/2BA | Pass-a-Grille Beach

2 bedrooms·2 baths
St. Pete Beach • Florida
4.99(71 reviews)

$4,173.38 USD $3,586.60 USD total for 7 nights

Nov 11 – 18, 2026

Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Pass-a-Grille Gulf Front Cottage, Ocean View
Beach. Steps from the cottage

Pass-a-Grille Gulf Front Cottage, Ocean View

1 bedroom·1 bath
St. Pete Beach • Florida
4.85(27 reviews)

$7,476.17 USD $6,392.55 USD total for 28 nights

Dec 1 – 29, 2026

The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage

The Coffee Pot Cottage

2 bedrooms·1 bath
St. Petersburg • Florida
5(26 reviews)

$610.76 USD $508.61 USD total for 3 nights

Oct 24 – 27, 2026

The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage

The Bayou Breeze Cottage

1 bedroom·1 bath
St. Petersburg • Florida
5(28 reviews)

$493.58 USD $410.86 USD total for 3 nights

Oct 31 – Nov 3, 2026

House
Bedroom
Ruhiges Zimmer mit tropischem Pool und Strandzugang
Pool Outdoor
Inside other

Ruhiges Zimmer mit tropischem Pool und Strandzugang

1 bedroom·1 bath
St. Petersburg • Florida
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

2 bedrooms·1 bath
St. Petersburg • Florida
5(268 reviews)
$139 – $1,999/ night(excl. fees & taxes)
Exterior view of Studio East & Studio West. Each studio has private entrance and private yard, connected with a gate.
Studio 1 (East) private porch
Studio 1 (East) private porch and outdoor
Studio 1 (East)
Studio 1 (East)

Adorable Pair - 2 private modern studios

2 bedrooms·2 baths
St. Petersburg • Florida
4.5(2 reviews)

$6,282.04 USD total for 28 nights

Nov 3 – Dec 1, 2026

Studio w/ yard & parking, near beach & downtown. image 1
Studio w/ yard & parking, near beach & downtown. image 2
Studio w/ yard & parking, near beach & downtown. image 3
Studio w/ yard & parking, near beach & downtown. image 4
Studio w/ yard & parking, near beach & downtown. image 5

Adorable Studio West, close to beaches & downtown

0 bedrooms·1 bath
St. Petersburg • Florida
4.72(50 reviews)

$2,881.44 USD $2,348.15 USD total for 28 nights

Nov 3 – Dec 1, 2026

Holiday Family Retreat. 4BR/3BA + Private Suites
Living room
Holiday Family Retreat. 4BR/3BA + Private Suites
Holiday Family Retreat. 4BR/3BA + Private Suites
Holiday Family Retreat. 4BR/3BA + Private Suites

Holiday Family Retreat. 4BR/3BA + Private Suites

4 bedrooms·3 baths
St. Petersburg • Florida
$399/ night(excl. fees & taxes)
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 1
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 2
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 3
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 4
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 5

Adorable Studio East, close to beaches & downtown

0 bedrooms·1 bath
St. Petersburg • Florida
4.88(41 reviews)

$2,881.44 USD $2,214.83 USD total for 28 nights

Oct 23 – Nov 20, 2026

Miscellaneous
Beach
Miscellaneous
Miscellaneous
Terrace/patio

Waterfront 3BR 2 1/2 Bath, Amazing View-Sunrises!

3 bedrooms·2½ baths
St. Pete Beach • Florida
5(3 reviews)

$13,750.00 USD total for 30 nights

Jan 1 – 31, 2027

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

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

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

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym
Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym
Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym
Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym
Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

6 bedrooms·3½ baths
Tampa • Florida
5(55 reviews)

$7,288.50 USD $6,741.58 USD total for 3 nights

Oct 23 – 26, 2026

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room
#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room
#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room
#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room
#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

#1 Rated Mansion • Heated Pool/Spa • Theater • Gym • Game Room

6 bedrooms·4 baths
Tampa • Florida

$4,466.56 USD total for 3 nights

Oct 23 – 26, 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)

$1,603.85 USD total for 5 nights

Oct 28 – Nov 2, 2026