Uitgelicht
Private courtyard patio with dining for 4.
Private courtyard patio
Courtyard patio
Exterior detail
Living area

Comforts of Home in Secure Gated Community Just 2 Miles from Anna Maria Island

2 bedrooms·2 baths
Bradenton • Florida
5(2 reviews)

$ 6.302,00 USD totaal voor 30 nachten

12 nov – 12 dec 2026

Chasing the Sun- Downtown Burns Court image 1
Chasing the Sun- Downtown Burns Court image 2
Chasing the Sun- Downtown Burns Court image 3
Chasing the Sun- Downtown Burns Court image 4
Chasing the Sun- Downtown Burns Court image 5

Chasing the Sun- Downtown Burns Court

2 bedrooms·1 bath
Sarasota • Florida
4.95(62 reviews)

$ 1.158,00 USD totaal voor 7 nachten

15–22 dec 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 totaal voor 120 nachten

12 nov 2026 – 12 mrt 2027

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 totaal voor 3 nachten

12–15 nov 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)

$ 2.178,64 USD totaal voor 7 nachten

28 nov – 5 dec 2026

See beautiful sunsets from our pool. Lots of outdoor lighting.
French Doors in the master suite open up to the screened in pool area.
Queen bed with 2 large closets and a desk.
Two twin beds
Sitting area in the master bedroom.

Beautiful pool home in Paradise! 4 miles Siesta Key & Lido, 3 miles to downtown

3 bedrooms·2 baths
Sarasota • Florida

$ 1.300,00 USD totaal voor 3 nachten

28 nov – 1 dec 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)

$ 1.366,42 USD totaal voor 5 nachten

12–17 nov 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(4 reviews)

$ 10.594,58 USD $ 10.100,49 USD totaal voor 7 nachten

19–26 dec 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)

$ 1.239,92 USD totaal voor 3 nachten

30 nov – 3 dec 2026

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ nacht(excl. kosten & belastingen)
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)

$ 4.011,81 USD totaal voor 3 nachten

12–15 nov 2026

Sun Haven House - 4 mi to beach! 2 beds/2 baths image 1
Well equipped kitchen with full size appliances including a dishwasher.
King Size Bed; Nectar mattress, light cotton blanket along with linens
Queen size Nectar mattress in master bedroom with walk-in closet and adjoining bathroom with large shower.
Cozy mood lighting to enjoy tropical nights and conversation with a cool drink or two.

Sun Haven House - 4 mi to beach! 2 beds/2 baths

2 bedrooms·2 baths
Sarasota • Florida

$ 3.992,00 USD totaal voor 30 nachten

12 nov – 12 dec 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 totaal voor 28 nachten

15 apr – 13 mei 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 totaal voor 75 nachten

2 jan – 18 mrt 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 totaal voor 3 nachten

28 nov – 1 dec 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/ nacht(excl. kosten & belastingen)
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 totaal voor 3 nachten

15–18 nov 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(4 reviews)

$ 5.391,20 USD totaal voor 7 nachten

7–14 dec 2026

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 totaal voor 5 nachten

12–17 nov 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)

$ 2.141,35 USD totaal voor 7 nachten

14–21 nov 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 totaal voor 60 nachten

12 nov 2026 – 11 jan 2027

The Casa Blanca resort beach offers free cabanas
Olympic sized heated pool
White sandy beaches
Frolicking birds
Private villa with screened porch 2 villas from beach

Sun & Sand ~ “Happy Place Villa” Steps to Beach

2 bedrooms·1 bath
Siesta Key • Florida
5(13 reviews)

$ 1.525,50 USD $ 1.426,63 USD totaal voor 5 nachten

12–17 nov 2026

Our Private Beach with chairs and umbrellas all included!!
Just a day at our private beach
Sandy's Siesta Key Condo
Sandy's Siesta Key Condo
Sandy's Siesta Key Condo

Sandy's Siesta Key Condo

2 bedrooms·1½ baths
Sarasota County • Florida

$ 1.200,01 USD totaal voor 7 nachten

12–19 nov 2026

Pool
Outdoor dining
Drone view of Crescent Property.
Beachside
Interior

Crescent Siesta Key Unit 406.

2 bedrooms·2 baths
Siesta Key • Florida
5(76 reviews)

$ 4.639,75 USD $ 4.442,00 USD totaal voor 7 nachten

12–19 nov 2026