Location

Dates

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Vacation rentals in Siesta Key, Florida, United States

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

Perfect Sarasota Getaway:Close to all /Heated Pool

3 bedrooms·2 baths

Sarasota • Florida

4.89(18 reviews)

$ 1.406,85 USD totaal voor 3 nachten

18–21 nov 2026

*Close to Beach/Downtown*Heated Pool*Game Room* Fire Pit

*Close to Beach/Downtown*Heated Pool*Game Room* Fire Pit

*Close to Beach/Downtown*Heated Pool*Game Room* Fire Pit

Primary bedroom with king bed and a slider out to the covered pool area. There is also a full bathroom with walk in shower.

Kitchen with granite countertops and all new appliances. There is also a pass through window to the outdoor bar area

Close to Beach/DowntownHeated PoolGame Room Fire Pit

3 bedrooms·2 baths

Sarasota • Florida

$ 1.028,30 USD totaal voor 3 nachten

18–21 nov 2026

balcony + Gulf view

Living room with Gulf view

Beachfront Escape – Private Balcony, Gulf Views image 5

Panoramic Gulf View with Amazing Sunset.

1 bedroom·1 bath

Longboat Key • Florida

4.87(223 reviews)

$ 1.227,18 USD totaal voor 3 nachten

29 nov – 2 dec 2026

Renovated Beach Paradise. Ground Floor unit 64 image 1

Turtle Crawl Inn 64

1 bedroom·1 bath

Longboat Key • Florida

4.88(73 reviews)

$ 1.022,65 USD totaal voor 3 nachten

28 nov – 1 dec 2026

Right on the beach.Renovated ground Floor unit 63. image 1

Right on the beach.Renovated ground Floor unit 63. image 5

Turtle Crawl Inn 63

0 bedrooms·1 bath

Longboat Key • Florida

4.74(88 reviews)

$ 836,20 USD totaal voor 3 nachten

30 nov – 3 dec 2026

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

Gulf-to-Bay Living on Longboat Key

2 bedrooms·2 baths

Longboat Key • Florida

$ 25.878,00 USD totaal voor 120 nachten

18 nov 2026 – 18 mrt 2027

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

2 bedrooms·2 baths

Sarasota • Florida

$ 3.665,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

Screened in patio, table with seating for 8 and 2 bedrooms look out onto pool as well as the main living space.

Well maintained exterior with new roof and hurricane windows.

Master Bedroom, King bed with french doors to pool and screened in patio

Master Bedroom, King bed, ceiling fan and bedside lamps touch control with USB ports.

Master Bath walk in shower

3BR/2B Vacation Pool Home, Nokomis Fl Rental

3 bedrooms·2 baths

Nokomis • Florida

5(3 reviews)

$ 2.052,50 USD $ 1.872,25 USD totaal voor 7 nachten

18–25 nov 2026

Kings Gate Mobile Home

Kings Gate Mobile Home

Kings Gate Mobile Home

Kings Gate Mobile Home

Kings Gate Mobile Home

1 bedroom·1 bath

Nokomis • Florida

$ 3.275,00 USD totaal voor 30 nachten

18 nov – 18 dec 2026

IMG Academy, Heated Pool, Huge Game Room & Golf! image 1

IMG Academy, Heated Pool, Huge Game Room & Golf! image 2

IMG Academy, Heated Pool, Huge Game Room & Golf! image 3

IMG Academy, Heated Pool, Huge Game Room & Golf! image 4

IMG Academy, Heated Pool, Huge Game Room & Golf! image 5

Sunny Bradenton Oasis, Pool/ Near Beaches & Golf!

4 bedrooms·2 baths

Bradenton • Florida

$ 1.151,47 USD $ 1.105,19 USD totaal voor 3 nachten

11–14 dec 2026

Welcome to The Beach on Longboat Key, Unit 224!

Located mid-island, gulfside!

It's the good life.

White sand and turquoise waters!

Condo With a View 4: On the Beach!

1 bedroom·1 bath

Longboat Key • Florida

4.96(26 reviews)

$ 994,40 USD totaal voor 3 nachten

18–21 nov 2026

Guest Bedroom converted to a king bed

Sea Club III #4 2B / 2B Direct Beachfront Condo by RVA

2 bedrooms·2 baths

Longboat Key • Florida

$ 1.820,00 USD totaal voor 5 nachten

18–23 nov 2026

Carriage homes, four to a building. Ours is bottom right with light blue car in driveway/garage area.

Enjoy fishing or kayaking from our lakes, this lake is connected to four other lakes accessible via kayak.

Spacious living room with Smart TV and the VIEW!!!

Private ground floor patio/lanai.

Resort Living Turnkey Carriage Home, waterfront

2 bedrooms·2 baths

Venice • Florida

$ 10.466,36 USD totaal voor 90 nachten

18 nov 2026 – 16 feb 2027

Casa Milly image 1

Casa Milly image 2

Casa Milly image 3

Casa Milly image 4

Casa Milly image 5

Casa Milly

2 bedrooms·1 bath

Bradenton • Florida

5(36 reviews)

$ 600,00 USD totaal voor 3 nachten

18–21 nov 2026

Lush and tropical!

Welcome to Silver Sands on Longboat Key!

Stroll north or south on the beach or just sit and wait for the sunrise or sunset -- you've got time.

Silver Sands Gulf Beach Resort!

White sandy beach - ideal!

Tropical Beach Condo!

1 bedroom·1 bath

Longboat Key • Florida

5(11 reviews)

$ 994,40 USD totaal voor 3 nachten

23–26 nov 2026

Our home is in the left side of the picture.

The front of our home.

Established 2019

Craig House with Heated Pool

3 bedrooms·2 baths

Bradenton • Florida

4.8(107 reviews)

$ 1.430,60 USD $ 1.370,12 USD totaal voor 5 nachten

14–19 jan 2027

Venice Pool Home | Easy Drive to Beach image 1

Venice Pool Home | Easy Drive to Beach image 2

Venice Pool Home | Easy Drive to Beach image 3

Venice Pool Home | Easy Drive to Beach image 4

Venice Pool Home | Easy Drive to Beach image 5

Venice Pool Home | Easy Drive to Beach

3 bedrooms·2 baths

Venice • Florida

$ 815,00 USD totaal voor 3 nachten

18–21 nov 2026

Beautiful Resort-Style Gran Paradiso Townhouse

Gran Paradiso Community

Beautiful Resort-Style Gran Paradiso Townhouse

3 bedrooms·2½ baths

Venice • Florida

$150/ nacht(excl. kosten & belastingen)

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths

Bradenton • Florida

$ 7.466,97 USD totaal voor 3 nachten

18–21 nov 2026

Backyard Oasis: Dive into relaxation with a sparkling pool and spa, surrounded by lush greenery!

Exterior: Vibrant sunsets and lush greenery await you in this stunning Bradenton retreat!

Living room with leather sofa, chairs and coffee table

Fully equipped kitchen with stainless steel appliances including French Door refrigerator with water and ice maker in door, glass electric stove, oven, microwave, coffee maker, electric tea kettle, dishes, cooking and baking pans, pots

Wood dining table

Heated Pool, Spa, BBQ, Games, Fire Pit, Sleeps 10

3 bedrooms·2 baths

Bradenton • Florida

5(75 reviews)

$ 831,00 USD totaal voor 3 nachten

23–26 nov 2026

Close to beautiful Venice Beach

Close to beautiful Venice Beach

Close to beautiful Venice Beach

Close to beautiful Venice Beach

Close to beautiful Venice Beach

Close to beautiful Venice Beach

1 bedroom·1 bath

Venice • Florida

$ 240,00 USD totaal voor 3 nachten

18–21 nov 2026

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater

6 bedrooms·4 baths

Bradenton • Florida

$ 2.825,76 USD totaal voor 3 nachten

18–21 nov 2026

Perfect place to relax, read a book, and cool down with a dip in crystal clear pool with water fall feature

Front entry way

Sun Soaked Paradise - Heated Pool image 5

Living room with ample seating large television.

Sun Soaked Paradise - Heated Pool

3 bedrooms·2 baths

Bradenton • Florida

5(3 reviews)

$ 980,00 USD totaal voor 3 nachten

19–22 nov 2026

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

Golf Course and Private Pool Views

2 bedrooms·2 baths

Manatee County • Florida

$ 13.700,00 USD totaal voor 60 nachten

18 nov 2026 – 17 jan 2027