3222+ Vacation Rentals Near Sarasota Square |
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Guide For Orlando - Vacation Rentals in Sarasota Square

A Bayside Treasure - Outstanding Waterfront Views! From US $241
         

10.0 (209 Reviews)
Condo
A Bayside Treasure - Outstanding Waterfront Views!
  • Air Conditioner
  • Parking
  • Pool

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South Sarasota Apartment From US $195
         

8.3 (3 Reviews)
Apartment
South Sarasota Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

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Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub From US $997
         

New
House
Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub
  • Air Conditioner
  • Pet Friendly
  • Pool

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On Siesta Key Beach, View, pool, 2 Bed 2 Ba, plus pull out Queen, From US $357
         

10.0 (187 Reviews)
Condo
On Siesta Key Beach, View, pool, 2 Bed 2 Ba, plus pull out Queen,
  • Air Conditioner
  • Parking
  • Pool

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Casa Coquina - 1038U From US $1,759
         

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10.0 (3 Reviews)
House
Casa Coquina - 1038U
  • Parking
  • Pet Friendly
  • View

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Siesta Sands Beach Resort Gulf View From US $719
         

10.0 (1 Review)
Condo
Siesta Sands Beach Resort Gulf View
  • Parking
  • Pool
  • View

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Location,Location,Location-Beachfront-Your Slice of Paradise-#1 Beach in America From US $457
         

9.8 (116 Reviews)
Condo
Location,Location,Location-Beachfront-Your Slice of Paradise-#1 Beach in America
  • Air Conditioner
  • Parking
  • Pool

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Fiesta Playa - 1027 From US $1,196
         

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10.0 (3 Reviews)
House
Fiesta Playa - 1027
  • Parking
  • Pool
  • Accessibility

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Coastal Breeze Siesta - Turtle From US $419
         

10.0 (1 Review)
Condo
Coastal Breeze Siesta - Turtle
  • Parking
  • View
  • Ocean View

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Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale - Renovated From US $326
         

9.8 (41 Reviews)
Condo
Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale - Renovated
  • Air Conditioner
  • Parking
  • Pool

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Escape to Paradise: Updated Sarasota Retreat near Siesta Key Beach and Pool! From US $200
         

9.6 (49 Reviews)
House
Escape to Paradise: Updated Sarasota Retreat near Siesta Key Beach and Pool!
  • Air Conditioner
  • Parking
  • Pool

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Exceptional Beachfront condo on Crescent Beach From US $541
         

10.0 (118 Reviews)
Condo
Exceptional Beachfront condo on Crescent Beach
  • Air Conditioner
  • Parking
  • Pool

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Cozy cottage in Gulf Gate to relax year-round in beautiful Sarasota. From US $176
         

10.0 (54 Reviews)
House
Cozy cottage in Gulf Gate to relax year-round in beautiful Sarasota.
  • Air Conditioner
  • Parking
  • TV

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1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ From US $412
         

9.6 (121 Reviews)
House
1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beachfront Property - Luxury Penthouse - Great Location! From US $482
         

9.6 (45 Reviews)
Condo
Beachfront Property - Luxury Penthouse - Great Location!
  • Air Conditioner
  • Parking
  • Pool

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Home for vacation rental in Sarasota, FL From US $174
         

9.6 (45 Reviews)
House
Home for vacation rental in Sarasota, FL
  • Air Conditioner
  • Parking
  • TV

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Romantic Lakefront Two bedroom unit W/access to Heated Pool and More From US $618
         

9.2 (33 Reviews)
House
Romantic Lakefront Two bedroom unit W/access to Heated Pool and More
  • Air Conditioner
  • Parking
  • Pool

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Luxury, New Construction Home - Serene and Private Vacation Oasis From US $203
         

9.8 (101 Reviews)
House
Luxury, New Construction Home - Serene and Private Vacation Oasis
  • Air Conditioner
  • Parking
  • Pool

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Great place to see the dolphins! And less than half a mile from Turtle Beach From US $263
         

9.6 (137 Reviews)
Apartment
Great place to see the dolphins! And less than half a mile from Turtle Beach
  • Air Conditioner
  • Parking
  • TV

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WINTER SPECIAL! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi From US $380
         

9.6 (49 Reviews)
Villa
WINTER SPECIAL! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi
  • Air Conditioner
  • Parking
  • Pet Friendly

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Relaxing Siesta Key Condo From US $231
         

9.8 (40 Reviews)
Condo
Relaxing Siesta Key Condo
  • Air Conditioner
  • Parking
  • Pool

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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale From US $326
         

9.6 (25 Reviews)
Condo
Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale
  • Air Conditioner
  • Parking
  • Pool

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Red Lifeguard Stand - pet freindly From US $206
         

9.6 (24 Reviews)
Apartment
Red Lifeguard Stand - pet freindly
  • Air Conditioner
  • Pet Friendly
  • TV

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Renovated condo with easy beach access on Siesta From US $494
         

9.4 (79 Reviews)
Condo
Renovated condo with easy beach access on Siesta
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Guidefororlando makes it easy to compare the best listings on Guidefororlando homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Guidefororlando homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sarasota Square.

Weather in Sarasota Square

View the weather forecast for Sarasota Square before booking your Sarasota Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Sarasota Square, FL

Guidefororlando offers a large selection of top attractions around Sarasota Square. Research things to do on your vacation before you visit Sarasota Square.


Lido Beach Venice Beach Siesta Key Beach St. Armands Circle Turtle Beach Nokomis Beach Sarasota Jungle Gardens Mote Marine Laboratory & Aquarium Sarasota Memorial Hospital John and Mable Ringling Museum of Art Crescent Beach Siesta Key Marina Myakka River State Park Sarasota Opera House Mall at University Town Center Marie Selby Botanical Gardens Marina Jack Ca dZan Longboat Key Beaches Sarasota Classic Car Museum

Sarasota Square Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Sarasota Square?

There are a lot of options in Sarasota Square. If you plan on staying in the Sarasota Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sarasota Square:

How many vacation rentals are available in Sarasota Square?

Currently, the total number of properties listed in 2026 is over 3222 in the Sarasota Square area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sarasota Square.