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
81-100 out of 108
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Gertrude'S Village House - In The Top Location! Siesta Key
Map1.3 mi from City Centre200 yd from Siesta Key Village
Select
Gulf Side, Spacious 1 Bedroom, 1 Bath, 200 Steps To Crescent Beach Siesta Key
Map800 yd from City Centre1500 yd from Siesta Beach
Select
Siesta Key Dream Inn Rental - Close To Village!
Map1.2 mi from City Centre200 yd from Siesta Key Village
FromUS$ 295 /nightSelect
Charming Two Bedroom Condo With Pool View Siesta Key Bay Oaks
Map1400 yd from City Centre1.2 mi from Siesta Beach
Select
Crystal Sands By Beachside Management
MapSteps from Crescent Beach100m
  • Plunge pool with sea views
  • Fully equipped kitchen available
  • Private entrance for added privacy
  • Plunge pool
  • Private entrance
  • Fully equipped kitchen
Hotel with modern amenities near stunning beaches
FromUS$ 705 /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
Family Apartment With Pool In Siesta Key Florida
MapSiesta Key Beach500m
  • Private pool for exclusive use
  • Steps from Siesta Key Beach
  • Two bedrooms for families
  • Private Pool
  • Indoor Pool
  • Flat-Screen TV
Hotel featuring private pool and family-friendly rooms
FromUS$ 1 214 /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
Coastal Surfside Swank By Beachside Management
Map1.1 mi from City Centre600 yd from Siesta Key Village
FromUS$ 1 027 /nightSelect
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
Select
Imperial Sunsets On Siesta
Map1.6 mi from City Centre900 yd from Siesta Key Village
Select
Beach Terrace On Siesta
Map1.2 mi from City Centre500 yd from Siesta Key Village
Select
Turtle Beach Hideaway
Map1.6 mi from City Centre1600 yd from Siesta Key Village
Select

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