Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard
Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard
Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard
Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard
Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

Casa Mar - Unit 55 ; 1 Bedroom 1 Bath Courtyard

1 bedroom·1 bath
Siesta Key • Florida

$ 941,60 USD totaal voor 3 nachten

26–29 okt 2026

Casa mar - Unit 74
Casa mar - Unit 74
Casa mar - Unit 74
Casa mar - Unit 74
Casa mar - Unit 74

Casa mar - Unit 74

1 bedroom·1 bath
Siesta Key • Florida

$ 873,20 USD totaal voor 3 nachten

26–29 okt 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)
Entire home in North Port, Florida
Entire home in North Port, Florida
Entire home in North Port, Florida
Entire home in North Port, Florida
Entire home in North Port, Florida

Entire home in North Port, Florida

4 bedrooms·1 bath
North Port • Florida
5(25 reviews)

$ 560,00 USD totaal voor 3 nachten

26–29 okt 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 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

Coral cottage 2 miles to the beach bring your boat image 1
Coral cottage 2 miles to the beach bring your boat image 2
Coral cottage 2 miles to the beach bring your boat image 3
Coral cottage 2 miles to the beach bring your boat image 4
Coral cottage 2 miles to the beach bring your boat image 5

Coral cottage 2 miles to the beach bring your boat

2 bedrooms·1 bath
Englewood • Florida

$ 396,00 USD totaal voor 3 nachten

26–29 okt 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(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

Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan
Paradiso Banyan

Paradiso Banyan

2 bedrooms·2 baths
Sarasota • Florida
$150/ nacht(excl. kosten & belastingen)
Englewood Escape: 3BR Water-Front with Pool
Englewood Escape: 3BR Water-Front with Pool
Englewood Escape: 3BR Water-Front with Pool
Englewood Escape: 3BR Water-Front with Pool
Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

3 bedrooms·2 baths
Englewood • Florida

$ 832,50 USD totaal voor 3 nachten

26–29 okt 2026

Simple Old Florida Style Home image 1
Simple Old Florida Style Home image 2
Simple Old Florida Style Home image 3
Simple Old Florida Style Home image 4
Simple Old Florida Style Home image 5

Bring your motorboat:Simple Old Florida Style Home

2 bedrooms·2 baths
Englewood • Florida

$ 460,86 USD totaal voor 4 nachten

26–30 nov 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

Abigial's Cottage Snowbird & pet friendly
Abigial's Cottage Snowbird & pet friendly
Abigial's Cottage Snowbird & pet friendly
Abigial's Cottage Snowbird & pet friendly
Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

2 bedrooms·2 baths
North Port • Florida

$ 866,00 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

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

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

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

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

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

Master king bedroom with en suite bathroom
Home with hot tub, 5 miles to Englewood beach image 2
Home with hot tub, 5 miles to Englewood beach image 3
Home with hot tub, 5 miles to Englewood beach image 4
Home with hot tub, 5 miles to Englewood beach image 5

Home with hot tub, 5 miles to Englewood beach

2 bedrooms·2 baths
Englewood • Florida
4.98(54 reviews)

$ 430,00 USD totaal voor 3 nachten

26–29 okt 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 totaal voor 7 nachten

9–16 nov 2026

3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3 bedrooms·2 baths
North Port • Florida

$ 840,00 USD totaal voor 3 nachten

26–29 okt 2026