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Vacation rentals in Siesta Key, United States

Carefully selected & verified rentals in Siesta Key, United States
Check-in
26Aug2025Select date
Check-out
27Aug2025Select date
Rooms and Guests2 Guests, 1 Room
View map
41-60 out of 108
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Siesta Key Dream Inn Vacation Rental Near Village!
Map1.2 mi from City Centre200 yd from Siesta Key Village
FromUS$ 364 /nightSelect
Comfortable Siesta Key Condo With Pool Access!
MapNearby Crescent Beach access400m
  • Outdoor swimming pool available for guests
  • Easy access to Crescent Beach nearby
  • Fully equipped kitchen in the rooms
  • Swimming pool
  • Beach access
  • Tennis court
Condo with pool access near stunning beach areas
FromUS$ 585 /nightSelect
Breezy Siesta Key Condo With Bay Views And Pool!
MapCrescent Beach700m
  • Outdoor swimming pool for relaxation
  • Tennis court for active guests
  • Spacious rooms with private entrance
  • Outdoor pool
  • Tennis court
  • Fitness centre
Condo resort featuring bay views and family-friendly amenities
Select
You Can'T Get Closer To The Beach Than This Beachy 3 Bedroom Condo
MapBeautiful Siesta Key Beach200m
  • Steps from Siesta Key Beach access
  • Private entrance for added privacy
  • Air-conditioned rooms with full kitchen
  • Beach Access
  • Flat-screen TV
  • Private Entrance
Beachfront condo with garden and family-friendly amenities
FromUS$ 662 /nightSelect
Heated Pool-Short Walk To Beach, Free Trolley Around Siesta Key!
4 adults
2 bedrooms
2 beds
MapCrescent Beach400m
  • Air-conditioned rooms with pool views
  • Heated outdoor swimming pool available
  • Free private parking included
  • Heated pool
  • Free parking
  • Air conditioning
Spacious hotel with private access and heated pool
FromUS$ 194 /nightSelect
Midnight Cove #714, Bayside In Siesta Key, Fl
4 adults
2 bedrooms
2 beds
MapCrescent Beach500m
  • Private beach access for guests
  • Heated outdoor pool with scenic views
  • Tennis courts available on-site
  • Heated pool
  • Tennis courts
  • Fitness centre
Resort offering beachfront access and recreational activities
FromUS$ 155 /nightSelect
Siesta Palms By The Beach
Map1.6 mi from City Centre300 yd from
Select
Lido Islander Inn And Suites - Sarasota
The largest option:
6 adults
Map3.7 mi from City Centre300 yd from
FromUS$ 235 /nightSelect
A Tide That Binds Us By Beachside Management
MapNear Siesta Key Beach200m
  • Stunning sea view rooms
  • Private entrance for each room
  • Well-fitted kitchens in all rooms
  • Private entrance
  • Well-fitted kitchens
  • Free parking
Seaside hotel with family-friendly amenities and services
FromUS$ 423 /nightSelect
Island House Beach Resort
The largest option:
4 adults
2 bedrooms
2 beds
Map1300 yd from City Centre1.1 mi from Siesta Beach
FromUS$ 352 /nightSelect
Direct Beachfront Delight By Beachside Management
6 adults
2 bedrooms
1 bed
MapNearby Siesta Key Beach300m
  • Direct beachfront access with stunning views
  • Fully equipped kitchen for self-catering needs
  • Private entrance for added privacy and comfort
  • Beachfront Access
  • Fully Equipped Kitchen
  • Private Entrance
Hotel featuring beach access and private accommodations
FromUS$ 617 /nightSelect
New Siesta Key Canal View
Map1.0 mi from City Centre
Select
The Village Breeze 6Br With Heated Pool, Near Beach, 250Ft To Siesta Key Village!
Map1.3 mi from City Centre300 yd from Siesta Key Village
Select
The Village Breeze - 2 Units, 4Br, 4Bath, Pool, Beach- Siesta Village Living!
Map1.3 mi from City Centre300 yd from Siesta Key Village
Select
The Village Breeze II - White-Sand, Pool, Beaches, Daiquiris, Seafood!
Map1.3 mi from City Centre300 yd from Siesta Key Village
Select
Village Breeze III - Heated Pool, Private Patio, Village And Beach!
Map1.3 mi from City Centre300 yd from Siesta Key Village
Select
The Village Breeze I - Heated Pool, Beaches, Daiquiris, Seafood, White-Sand!
Map1.3 mi from City Centre300 yd from Siesta Key Village
Select
Siestakeyvillageheated Pool
Map1.1 mi from City Centre300 yd from Siesta Key Village
Select
Siesta Key Village Heated Pool
Map1.1 mi from City Centre300 yd from Siesta Key Village
Select
6415 Midnight Pass #801
Map1.2 mi from City Centre300 yd from
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Flexible Price Range for Vacation Homes in Siesta Key

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 1 257
⬇️ The lowest price
US$ 155
đź’¸ Average price for
Apartments
US$ 449

How to get to Siesta Key

Explore local transportation options with ease

Airports
Sarasota Bradenton International (SRQ)

FAQs about Siesta Key rentals

Get answers to common questions and plan your adventure smoothly

What are the best vacation rentals for families in Siesta Key?
Properties like Our House At The Beach 502E and Paradise Beach Villas are recommended for families due to their spacious accommodations and proximity to family-friendly activities. Both offer easy access to the beach and outdoor pools.
Which vacation rentals are ideal for couples in Siesta Key?
Turtle Beach Resort offers a romantic setting with beachfront access, while the Oceanview Penthouse provides stunning views, making them perfect for couples looking for a getaway.
Which vacation rentals are located near popular sites in Siesta Key?
Beachpoint Cottages and Living The Dream are both situated within walking distance to Siesta Key Beach and local dining options, providing convenient access to popular attractions.
What amenities do the highest-rated vacation rentals in Siesta Key offer?
Top-rated properties like Siesta Key Condo - On The Water and Beachfront Getaway In Siesta Key include amenities such as direct beach access, pools, and kitchen facilities, receiving high guest reviews for cleanliness and location.

Essential Facts About Vacation Rentals in Siesta Key

This guide provides essential information on vacation rentals in Siesta Key, evaluating 1 property to assist travelers in making informed accommodation decisions.

Typical nightly prices range from $150 to $400.

There is 1 prominent vacation rental property option available.

Peak travel seasons are during winter and summer.

Local taxes and fees approximate 12% on rental costs.

Properties are generally within 1-2 miles of Siesta Beach and the Village area.

Check-in
26Aug2025Select date
Check-out
27Aug2025Select date
Rooms and Guests2 Guests, 1 Room
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