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)

$ 1.168,00 USD total por 3 noites

24 – 27 de set. de 2026

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)

$ 1.474,96 USD total por 3 noites

24 – 27 de set. de 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)

$ 2.384,30 USD total por 7 noites

24 – 31 de out. de 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 por 7 noites

19 – 26 de dez. de 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)

$ 1.581,74 USD total por 5 noites

24 – 29 de set. de 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 por 3 noites

4 – 7 de out. de 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 por 3 noites

26 – 29 de set. de 2026

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ noite(excl. taxas & impostos)
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)

$ 3.564,33 USD total por 3 noites

24 – 27 de set. de 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 por 28 noites

15 de abr. – 13 de mai. de 2027

Front of house.
Wind Swept Pass a Grille- Beach is across the street.
Wind Swept Pass a Grille- Beach is across the street.
Beautiful day at the beach
Wind Swept Pass a Grille- Beach is across the street.

Wind Swept Pass a Grille- Beach is across the street.

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

$ 3.653,65 USD total por 7 noites

24 de set. – 1 de out. de 2026

Pass a Grille Historic Cottage- Beach is across the street.
Beach. Steps from the cottage
Cozy Kitchen. Small but lots of space to cook
Pass a Grille Historic Cottage- Beach is across the street.
Pass a Grille Historic Cottage- Beach is across the street.

Pass a Grille Historic Cottage- Beach is across the street.

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

$ 7.401,06 USD total por 28 noites

31 de mar. – 28 de abr. de 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 por 3 noites

8 – 11 de out. de 2026

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 por 3 noites

8 – 11 de out. de 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/ noite(excl. taxas & impostos)
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)

$ 13.392,70 USD total por 14 noites

12 – 26 de dez. de 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 por 14 noites

21 de out. – 4 de nov. de 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 por 14 noites

24 de set. – 8 de out. de 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 por 7 noites

26 de set. – 3 de out. de 2026

The tiny home sits on a private 1.5 acre inland peninsula!
[Patio] Shared outdoor living space with fire pit
[Living area] This luxury 270sqft craftsman style tiny home is in the ideal location for your beach getaway.
Outdoor dining options available in the screened in lounge.
[Kitchen] Fully equipped kitchen featuring stainless steel appliances & gas cooktop. Coffee maker for all the coffee lovers out there!

·@Tiffanythetinyhome| island | netflix|bike|hammock

1 bedroom·1 bath
Sarasota • Florida
$119 – $168/ noite(excl. taxas & impostos)
[Living area] Smart TV with Netflix & Hulu
Waterfront tiny home sits on a private 1.5 acre inland peninsula! The perfect location for bird watching & kayaking around the lake.
[Living area] Doorway to the left leads into the main bedroom.
[Kitchen] Fully stocked & equipped kitchen with large farm sink and convection cooktop.
[Living area] French doors open up into the spacious backyard. Sofa converts into a bed for additional sleeping space.

@Shellmateisland |tiny home| island| bikes| kayaks

1 bedroom·1 bath
Sarasota • Florida
$158 – $234/ noite(excl. taxas & impostos)
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b
Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

Bermuda Bay Beach and Racquet Club Condo. 2bdrm/2b

2 bedrooms·2 baths
St. Petersburg • Florida
4.67(12 reviews)
$60 – $143/ noite(excl. taxas & impostos)
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)
$300/ noite(excl. taxas & impostos)
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)

$ 2.264,65 USD total por 5 noites

24 – 29 de set. de 2026