Vacation rentals in Siesta Key

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Top-rated holiday rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Siesta Key
Siesta Key #1 Beach, pickle ball & tennis paradise
Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines
16 – 23 Sept
4.99 out of 5 average rating, 135 reviews
Guest favourite
Island in Sarasota
*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*
Check our nearby sister property for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, check out our VIDEOS!
5 – 12 Nov
4.98 out of 5 average rating, 296 reviews
Guest favourite
Home in Siesta Key
Siesta Key, FL - Casa Berano
Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs
22 – 29 Sept
4.89 out of 5 average rating, 101 reviews

Popular amenities for Siesta Key holiday rentals

Stay near Siesta Key's top sights

The Cottage68 locals recommend
Phillippi Estate Park17 locals recommend
PARASAIL SIESTA24 locals recommend
Siesta Beach Pavillion3 locals recommend
Siesta Key Oyster Bar167 locals recommend
South Lido Key Beach Park on the Gulf25 locals recommend

Other great holiday rentals in Siesta Key

Guest favourite
Condo in Siesta Key
Amazing beach view! Entire unit renovated!
19 – 26 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Condo in Siesta Key
Palm Bay Club Most Desirable Spot on Siesta Key!
23 – 30 Jan
4.98 out of 5 average rating, 61 reviews
Guest favourite
Home in Siesta Key
Beachfront 180-Degree View, Walk to Village!
1 – 8 June
5.0 out of 5 average rating, 18 reviews
Guest favourite
Condo in Siesta Key
Crystal House on Siesta Key Beach
8 – 15 Nov
4.88 out of 5 average rating, 81 reviews
Guest favourite
Holiday home in Siesta Key
Siesta Beach View : Pineapple Bungalow Efficiency
19 – 26 July
5.0 out of 5 average rating, 54 reviews
Guest favourite
Condo in Siesta Key
2 BR condo in Siesta Key w/ Private beach access
13 – 20 May
4.97 out of 5 average rating, 33 reviews
Guest favourite
Condo in Siesta Key
Siesta Key Beach Front Condo
12 – 19 Aug
4.95 out of 5 average rating, 78 reviews
Guest favourite
Condo in Sarasota
615 Luxury Condo With Ocean View, Heated Pool +++
2 – 9 Feb
4.98 out of 5 average rating, 60 reviews
Superhost
Apartment in Siesta Key
Sunset Sensation
5 – 12 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Siesta Key
Coolest House in Siesta Key Village
14 – 21 Oct
5.0 out of 5 average rating, 43 reviews
Guest favourite
Condo in Siesta Key
Comfy Siesta Key Condo
26 Nov – 3 Dec
4.82 out of 5 average rating, 72 reviews
Guest favourite
Home in Siesta Key
Your Tropical Paradise at a Siesta Key Beach House
23 – 30 Sept
4.98 out of 5 average rating, 57 reviews

Quick stats about holiday rentals in Siesta Key

Total rentals

1.6K properties

Rentals with dedicated workspaces

680 properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

340 properties allow pets

Family-friendly rentals

1.3K properties are a good fit for families

Total number of reviews

28K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key