Cozy meets creative in this sunny lounge! Enjoy fast Wi-Fi, Smart TV, and artistic touches throughout—ideal for relaxing with a good show or planning your next St. Pete adventure.

Cozy Couples Artsy Retreat with Local Art Walkable

2 bedrooms·1 bath
$121 – $456/ night(excl. fees & taxes)
Cozy Dali Inspired Loft for Couples & Small Groups

Cozy Dali Inspired Loft for Couples & Small Groups

2 bedrooms·1 bath
$105 – $553/ night(excl. fees & taxes)
[Entrance] Self-check in with keypad

Outskirt Downtown | 400ft² | bikes | kayak|netflix

1 bedroom·1 bath
$156 – $355/ night(excl. fees & taxes)
[Living area] Smart TV with Netflix & sofa bed

Walk score 82 | bikes | kayak | 214mbps | foam bed

1 bedroom·1 bath
$106 – $293/ night(excl. fees & taxes)
Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

Sleeps 24-Beachfront Entire Resort- Outdoor Pool 7BR

7 bedrooms·7 baths
$595 – $3,112/ night(excl. fees & taxes)
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

2 bedrooms·2 baths
$200 – $1,630/ night(excl. fees & taxes)
Madeira Beachside - Pool & Steps to the Sand

Madeira Beachside - Pool & Steps to the Sand

1 bedroom·1 bath
$200 – $1,406/ night(excl. fees & taxes)
King Bed, Steps to Madeira Beach, Heated Pool, Private

King Bed, Steps to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
$200 – $1,540/ night(excl. fees & taxes)
King Bed, Step to Madeira Beach, Heated Pool, Private

King Bed, Step to Madeira Beach, Heated Pool, Private

1 bedroom·1 bath
$200 – $1,440/ night(excl. fees & taxes)
King Bed-Step to Madeira Beach-Heated Pool-Private

King Bed-Step to Madeira Beach-Heated Pool-Private

1 bedroom·1 bath
$200 – $1,440/ night(excl. fees & taxes)
Park & Pool Across the Street and 9 Mins to Beach image 1

Park & Pool Across the Street and 9 Mins to Beach

4 bedrooms·2 baths
4.95(43 reviews)
$149 – $556/ night(excl. fees & taxes)
Golf Course and Private Pool Views

Golf Course and Private Pool Views

2 bedrooms·2 baths
$225/ night(excl. fees & taxes)
Entrance to Sunray

SunRay

1 bedroom·1 bath
4(6 reviews)
$51 – $138/ night(excl. fees & taxes)
Blue Tide Retreat | Walk to Beach | Sleeps 4

Blue Tide Retreat | Walk to Beach | Sleeps 4

1 bedroom·1 bath
$149/ night(excl. fees & taxes)
Beachside Blue Retreat | Walk to Beach | Long-Term

Beachside Blue Retreat | Walk to Beach | Long-Term

1 bedroom·1 bath
$149 – $169/ night(excl. fees & taxes)
Sarasota vacation rental

Sarasota vacation rental

3 bedrooms·2 baths
$100/ night(excl. fees & taxes)
Shaded gazebo lounge with cushioned seating—private backyard retreat.

Family Retreat Near Siesta Key & Downtown Sarasota - Holiday Home

3 bedrooms·2 baths
5(6 reviews)
$105 – $175/ night(excl. fees & taxes)
Private studio/pets friendly/10 mins to Downtown

Private studio/pets friendly/10 mins to Downtown

0 bedrooms·1 bath
4.32(19 reviews)
$77/ night(excl. fees & taxes)
Florida Beachside Home

Florida Beachside Home

2 bedrooms·2 baths
5(12 reviews)
$179/ night(excl. fees & taxes)
FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath
5(1 review)
$210 – $332/ night(excl. fees & taxes)
Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths
5(26 reviews)
$525/ night(excl. fees & taxes)
Zach's Siesta Key Beach House

Siesta Beach | Heated Pool | Pet Friendly | Bike & Walk Friendly | Zach's Private Beach House

3 bedrooms·2 baths
4.4(5 reviews)
$361 – $1,382/ night(excl. fees & taxes)
The Walters 1

The Walters

3 bedrooms·2 baths
5(21 reviews)
$215 – $225/ night(excl. fees & taxes)
Common Area: 🌳 Spacious Outdoor w/ table and chairs

Private Deck • Pet Friendly • Spacious Courtyard

0 bedrooms·1 bath
$88 – $3,000/ night(excl. fees & taxes)