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

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

26 okt 2026 – 23 feb 2027

Heated pool & spa
Bathroom 1 bath/shower
Bathroom 2 walk in shower
Bedroom 1
Bedroom 3

Heated Pool & Spa 3bd/2bth, near Siesta Key Beach

3 bedrooms·2 baths
Sarasota • Florida

$ 600,00 USD totaal voor 3 nachten

26–29 okt 2026

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

26–29 okt 2026

Spotless & Tranquil Bungalow (Allergen Friendly)
Ra the Tortoise, he loves cucumbers so bring some snackies!
Spotless & Tranquil Bungalow (Allergen Friendly)
Spotless & Tranquil Bungalow (Allergen Friendly)
Spotless & Tranquil Bungalow (Allergen Friendly)

Spotless & Tranquil Bungalow (Allergen Friendly)

1 bedroom·1 bath
Parrish • Florida
5(82 reviews)

$ 718,80 USD totaal voor 3 nachten

1–4 mrt 2027

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 totaal voor 7 nachten

9–16 nov 2026

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)

$ 1.282,00 USD totaal voor 3 nachten

8–11 nov 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)

$ 1.862,55 USD totaal voor 3 nachten

7–10 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(2 reviews)

$ 11.383,59 USD $ 10.850,06 USD totaal voor 7 nachten

19–26 dec 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)

$ 2.095,02 USD totaal voor 7 nachten

26 okt – 2 nov 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)

$ 1.544,50 USD totaal voor 5 nachten

28 okt – 2 nov 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 totaal voor 3 nachten

1–4 nov 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 totaal voor 3 nachten

1–4 nov 2026

Heated pool
Siesta Key beach
Dusk view of front of building
Front door and porch area
Front door and sliding glass doors

Siesta Key Village Vacation Rental – Walk to Beach

2 bedrooms·1 bath
Sarasota • Florida

$ 749,30 USD totaal voor 3 nachten

26–29 okt 2026

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)

$ 3.610,66 USD totaal voor 3 nachten

26–29 okt 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

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ nacht(excl. kosten & belastingen)
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 totaal voor 14 nachten

12–26 dec 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

31 okt – 7 nov 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)

$ 3.580,96 USD $ 3.083,03 USD totaal voor 7 nachten

11–18 nov 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)

$ 7.345,33 USD $ 6.281,34 USD totaal voor 28 nachten

1–29 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)
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 totaal voor 14 nachten

26 okt – 9 nov 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 totaal voor 14 nachten

26 okt – 9 nov 2026