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      Villas in Siesta Key

      Compare 4 villas in Siesta Key with free parking, private beach, and plunge pools. Check rates and photos for family-friendly stays. Book now for exclusive deals.

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      Hotels
      Vacation rentals
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      Villas (4)Apartments (16)
      1-20 out of 20
      Sort by: high popularity
      • Price: low to high
      • Price: high to low
      • Guest rating: high to low
      • Popularity: high to low
      Crescent Arms CondominiumsHoliday home
      9.1
      Perfect12 total reviews
      our site & Booking.com
      5 adults
      2 bedrooms
      3 beds
      Map
      1.0 mi from City Center
      Full KitchenOutdoor PoolComplimentary Bikes
      • Private condos with full kitchens
      • Beachfront with outdoor pool
      • Complimentary bicycle rentals
      FromUS$ 753 /nightSelect
      Bay Oaks - 6157 #E01Holiday home
      9.0
      Perfect2 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1366 yd from City Center1.2 mi from Siesta Beach
      Outdoor PoolFishingKitchen
      • Holiday home with full kitchen
      • On-site fishing activities
      • Outdoor swimming pool
      FromUS$ 344 /nightSelect
      Bianco Sands By Beachside ManagementVilla
      8.9
      Great107 total reviews
      our site & Booking.com
      8 adults
      2 bedrooms
      4 beds
      Map
      1.7 mi from City Center
      Plunge PoolFull KitchenDryer
      • Plunge pool on premises
      • Private villa entrance
      • Full kitchen included
      FromUS$ 141 /nightSelect
      Crescent Beach Villas By Beachside ManagementVilla
      8.3
      Great26 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1.7 mi from City Center
      Plunge PoolFull KitchenPrivate Entrance
      • Full kitchen in every villa
      • Plunge pool on site
      • Private entrance per unit
      FromUS$ 253 /nightSelect
      Villa 27 - Premium Plus - W&D Aloha Kai Vacation VillasVilla
      10.0
      Perfect1 total review
      our site & Booking.com
      Map
      945 yd from City Center1541 yd from Siesta Beach
      Beach AccessOutdoor PoolFull Kitchen
      • Steps from Crescent Beach
      • Full kitchen and washer
      • Outdoor swimming pool
      Select
      The OasisHoliday home
      18 adults
      7 bedrooms
      7 beds
      Map
      1.4 mi from City Center276 yd from Siesta Key Village
      Water SlideHeated PoolBarbecue
      • 7-bedroom holiday home with balcony
      • Water slide in heated pool
      • Sea views from private balcony
      FromUS$ 2 013 /nightSelect
      The PlazaHoliday home
      17 adults
      8 bedrooms
      8 beds
      Map
      1556 yd from City Center768 yd from Siesta Key Village
      Private PoolBeach AccessFree Parking
      • Private pool and patio
      • Steps from Siesta Key Beach
      • Fully equipped kitchen
      FromUS$ 5 540 /nightSelect
      Siesta Key Beach 5830 #T34Holiday home
      6.8
      Nice15 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      2 beds
      Map
      518 yd from City Center978 yd from Siesta Beach
      Heated PoolBeach AccessFull Kitchen
      • Steps from Crescent Beach
      • On-site heated swimming pool
      • 24-hour front desk available
      FromUS$ 254 /nightSelect
      Beautiful Property On Siesta KeyVilla
      8.1
      Great61 total reviews
      our site & Booking.com
      4 adults
      2 bedrooms
      3 beds
      Map
      974 yd from City Center1.0 mi from Siesta Beach
      Private BeachPrivate PoolTennis Court
      • Private beach access included
      • Private pool with garden view
      • On-site tennis court available
      FromUS$ 200 /nightSelect
      Siesta Key Island RentalsHoliday home
      9.1
      Perfect61 total reviews
      our site & Booking.com
      2 adults
      1 bedroom
      2 beds
      Map
      1428 yd from City Center673 yd from Siesta Beach
      Indoor PoolOutdoor PoolHot Tub
      • Beach proximity with dual pools
      • Indoor and outdoor heated pools
      • On-site bike rental available
      FromUS$ 596 /nightSelect
      Siesta Key Beach HouseVilla
      8.4
      Great72 total reviews
      our site & Booking.com
      6 adults
      3 bedrooms
      4 beds
      Map
      977 yd from City Center1.0 mi from Siesta Beach
      Private BeachHeated PoolWater Sports
      • Private beach access included
      • Heated outdoor pool year-round
      • Water sports equipment on site
      FromUS$ 237 /nightSelect
      Siesta Heron Suites & VillasHoliday home
      8.9
      Great157 total reviews
      our site & Booking.com
      7 adults
      3 bedrooms
      4 beds
      Map
      2.9 mi from City Center
      Water SportsHeated PoolEV Charging
      • Water sports facilities on-site
      • Year-round heated outdoor pool
      • Electric vehicle charging station
      FromUS$ 179 /nightSelect
      Beachfront Siesta Key Condo W/ Enclosed PatioHoliday home
      5.5
      Needs improvement18 total reviews
      our site & Booking.com
      Map
      786 yd from City Center193 yd from Siesta Beach
      BeachfrontEnclosed PatioOutdoor Dining
      • Beachfront condo with patio
      • Outdoor dining area
      • Snorkeling gear provided
      FromUS$ 428 /nightSelect
      Siesta Key Beach - Tropea 665 #3Holiday home
      9.0
      Perfect25 total reviews
      our site & Booking.com
      4 adults
      1 bedroom
      1 bed
      Map
      1028 yd from City Center250 yd from Siesta Beach
      Beach accessPrivate parkingFully equipped kitchen
      • Steps from Siesta Key Beach
      • Full kitchen with dishwasher
      • Free private parking on-site
      FromUS$ 279 /nightSelect
      Heat Of Siesta Village Walk To Beach W Heated PoolHoliday home
      9.6
      Perfect16 total reviews
      our site & Booking.com
      Map
      1.3 mi from City Center196 yd from Siesta Key Village
      Heated PoolOutdoor PoolBeach Access
      • Heated outdoor pool on-site
      • Steps from Siesta Key Beach
      • Spacious 2-bedroom holiday home
      FromUS$ 273 /nightSelect
      Siesta Key Village, Heated Pool, Beach Access 4 Min Walk, 1BdrHoliday home
      9.3
      Perfect9 total reviews
      our site & Booking.com
      Map
      1.1 mi from City Center267 yd from Siesta Key Village
      Heated PoolPrivate PoolBeach Access
      • Private pool with heated option
      • 4-minute walk to public beach
      • On-site massage and foot bath
      FromUS$ 301 /nightSelect
      New Listing! Pool Jacuzzi, 3-Min To Beach Bars & Entertainment!Holiday home
      9.0
      Perfect11 total reviews
      our site & Booking.com
      Map
      1.5 mi from City Center
      Outdoor PoolHot TubTerrace
      • Year-round outdoor pool with hot tub
      • 3-minute walk to beach bars
      • On-site snorkeling and diving
      FromUS$ 933 /nightSelect
      Siesta Key Beach 665 #1Holiday home
      8.9
      Great18 total reviews
      our site & Booking.com
      6 adults
      2 bedrooms
      3 beds
      Map
      1028 yd from City Center250 yd from Siesta Beach
      Beach AccessPrivate ParkingFull Kitchen
      • 100m from Siesta Key Beach
      • Private parking on-site
      • Full kitchen with dishwasher
      FromUS$ 330 /nightSelect
      One-Of-A-Kindbeach, Village, Dock & Private Pool!Holiday home
      9.8
      Perfect8 total reviews
      our site & Booking.com
      Map
      1.1 mi from City Center321 yd from Siesta Key Village
      Private PoolPrivate DockSaltwater Pool
      • Private pool with saltwater
      • Beach access with private dock
      • Outdoor play equipment provided
      FromUS$ 599 /nightSelect
      Canal 313 - Right In Siesta Key Village!Holiday home
      9.7
      Perfect16 total reviews
      our site & Booking.com
      Map
      1.2 mi from City Center169 yd from Siesta Key Village
      Private PoolHeated PoolOutdoor Dining
      • Private pool with quiet street views
      • Steps from Siesta Key Beach
      • Two-bedroom holiday home layout
      FromUS$ 386 /nightSelect

      For visitors seeking space and privacy, the cluster of villas near Crescent Beach in Siesta Key offers a practical alternative to hotels. These holiday homes typically feature full kitchens, free parking, and direct beach access-perfect for families or groups. Budget expectations vary, but many properties include amenities like plunge pools and outdoor dining areas, making them ideal for longer stays. Booking early is recommended given the limited inventory, and most units require a minimum stay during peak season.

      Among top-rated options, Bianco Sands By Beachside Management scores 88/100 for its plunge pool and proximity to Crescent Beach. The Siesta Key Beach House (83/100) adds a private beach area and water sports gear, suitable for active travelers. Crescent Beach Villas By Beachside Management (82/100) offers a similar setup with easy beach access. For those wanting a private pool and tennis court, Beautiful Property On Siesta Key (79/100) provides a garden view and barbecue facilities. All properties include air conditioning and free WiFi.