Siesta Key Vacation Rentals: Top Siesta Key Rentals

Compare Siesta Key vacation rentals and Airbnbs from 78 options, including beachfront villas and homes with heated pools. Check prices and ratings before you book

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1-20 out of 74
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
9.1
Perfect
The largest option:
6 adults
2 bedrooms
3 beds
Map
1.3 mi from City Center360 yd from Siesta Key Village
Full KitchenBeach CartsTennis Court
  • Full kitchens in all cottages
  • Beach carts and chairs provided
  • Across from beach access points
FromUS$ 299 /nightSelect
8.8
Great
7 adults
3 bedrooms
3 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
8.9
Great
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
8.5
Great
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
9.2
Perfect
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$ 370 /nightSelect
8.7
Great
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
8.8
Great
4 adults
2 bedrooms
3 beds
Map
377 yd from City Center548 yd from Siesta Beach
Plunge PoolFull KitchenWasher/Dryer
  • Plunge pool with sea views
  • Private entrance for privacy
  • Fully equipped kitchen
FromUS$ 550 /nightSelect
10.0
Perfect
Map
1.4 mi from City Center
Heated PoolHot TubFitness Center
  • Steps from Crescent Beach
  • Full kitchens in all units
  • Heated outdoor pool and hot tub
FromUS$ 347 /nightSelect
9.2
Perfect
4 adults
1 bedroom
2 beds
Map
733 yd from City Center1547 yd from Siesta Beach
Heated PoolSun LoungersBarbecue Grill
  • On-the-water condo with pool view
  • Fully equipped kitchen and dining
  • Private garden with barbecue
FromUS$ 310 /nightSelect
8.7
Great
Map
1.4 mi from City Center
Full KitchenPrivate GardenOutdoor Dining
  • Fully equipped kitchen in apartment
  • Private garden with outdoor dining
  • Crescent Beach just 400 meters away
FromUS$ 224 /nightSelect
8.7
Great
The largest option:
4 adults
1 bedroom
2 beds
Map
1.5 mi from City Center397 yd from Siesta Key Village
Plunge PoolFree ParkingFull Kitchen
  • Plunge pool for private use
  • Steps from Siesta Key Beach
  • Full kitchen in each unit
FromUS$ 171 /nightSelect
9.4
Perfect
The largest option:
6 adults
2 bedrooms
3 beds
Map
1.3 mi from City Center327 yd from Siesta Key Village
Full KitchenBeach AccessIn-Unit Dryer
  • Full kitchen in every unit
  • Steps from Siesta Key Beach
  • Free on-site parking
FromUS$ 234 /nightSelect
5.3
Needs improvement
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
9.2
Perfect
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
7.6
Very good
Map
1.2 mi from City Center191 yd from Siesta Key Village
Free ParkingBeach AccessKitchenette
  • Steps from Siesta Key Beach
  • Spacious apartment with kitchenette
  • Free on-site private parking
FromUS$ 286 /nightSelect
8.3
Great
6 adults
2 bedrooms
3 beds
Map
1317 yd from City Center1.1 mi from Siesta Beach
Heated PoolPrivate PoolTennis Court
  • Free trolley access
  • Steps to heated pool
  • On-site billiards & tennis
FromUS$ 242 /nightSelect
8.5
Great
The largest option:
6 adults
2 bedrooms
3 beds
Map
516 yd from City Center1023 yd from Siesta Beach
Plunge PoolFull KitchenBarbecue
  • Steps from Crescent Beach
  • Plunge pool with sea views
  • In-unit washer and dryer
FromUS$ 420 /nightSelect
7.3
Very good
Map
1.2 mi from City Center188 yd from Siesta Key Village
Beach AccessFull KitchenBike Hire
  • 3-minute walk to Siesta Beach
  • Fully equipped kitchen with washer & dryer
  • Bike and car hire available
FromUS$ 312 /nightSelect
7.7
Very good
3 adults
1 bedroom
1 bed
Map
1028 yd from City Center250 yd from Siesta Beach
Beach AccessPrivate ParkingFull Kitchen
  • Steps from Siesta Key Beach
  • Free private on-site parking
  • Fully equipped kitchen in unit
FromUS$ 177 /nightSelect
9.2
Perfect
4 adults
1 bedroom
1 bed
Map
1028 yd from City Center250 yd from Siesta Beach
Beach AccessPrivate ParkingFull Kitchen
  • Steps from Siesta Key Beach
  • Fully equipped kitchen in unit
  • Private parking on site
FromUS$ 169 /nightSelect
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Siesta Key vacation rentals offer a direct alternative to hotels, with fully equipped kitchens, separate living areas, and private outdoor spaces. Budgets vary: one-bedroom villas start around $150 per night, while larger four-bedroom homes run higher. Most properties cluster near Crescent Beach or Siesta Key Village, putting you steps from the sand and local dining. Expect amenities like heated swimming pools, free WiFi, on-site parking, and barbecue areas. Many rentals include washing machines and dishwashers, making extended stays more practical than a standard hotel room.

Among the top-rated options, Affordable Ground Floor Siesta Key Vacation Rental (Superb, 9.0) provides a heated pool and a patio just five minutes from Crescent Beach. Midnight Cove II 823 (Fabulous, 8.6) offers direct beachfront access, a fitness room, and a garden. Crescent Royale Condominiums 301 (Exceptional, 10.0) sits a four-minute walk from Siesta Key Beach and features a massage service, games room, and sea views. For families, Crescent Cottage - 1034 (Very Good, 8.0) delivers a private pool and four bedrooms near the beach. These rentals suit travelers who want space, privacy, and resort-style perks without the formality of a full-service hotel.