Vacation rentals in Siesta Key, United States

Carefully selected & verified rentals in Siesta Key, United States
Check-in
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Check-out
27Aug2025Select date
Rooms and Guests2 Guests, 1 Room
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1-20 out of 110
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Crescent Arms Condominiums Siesta Key
5 adults
2 bedrooms
3 beds
MapCrescent Beach300m
  • Private beach access for relaxation
  • Outdoor pool with sun loungers available
  • Fully equipped kitchens in spacious rooms
  • Private beach
  • Outdoor pool
  • BBQ area
Beachfront resort with modern amenities and activities
FromUS$ 240 /nightSelect
Villa 27 - Aloha Kai Vacation Villas Siesta Key
Map1000 yd from City Centre1600 yd from Siesta Beach
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Beachpoint Cottages
The largest option:
6 adults
2 bedrooms
3 beds
MapBeautiful Siesta Key beach200m
  • Direct beach access available
  • Full kitchens in every room
  • On-site beach chairs provided
  • Beach access
  • Full kitchens
  • Outdoor dining
Charming hotel offering beachside cottages on Siesta Key
FromUS$ 369 /nightSelect
Gulf Holiday By Beachside Management
The largest option:
4 adults
1 bedroom
2 beds
MapNearby Crescent Beach200m
  • Steps from Siesta Key Beach
  • Equipped kitchens in rooms
  • Plunge pool available on-site
  • Plunge pool
  • Private entrance
  • On-site parking
Beachside hotel with private, well-equipped rooms
FromUS$ 171 /nightSelect
Walk To The Beach - Island Villa
Map1.1 mi from City Centre400 yd from Siesta Key Village
FromUS$ 263 /nightSelect
Beachfront Getaway In Siesta Key
Map1.4 mi from City Centre300 yd from
FromUS$ 224 /nightSelect
A Somewhere Is Here By Beachside Management
MapSiesta Key Beach300m
  • Plunge pool for relaxation
  • Private entrance for rooms
  • Well-fitted kitchens available
  • Plunge pool
  • Air conditioning
  • Private bathroom
Hotel with private access to beachside relaxation
FromUS$ 664 /nightSelect
Our House At The Beach 502E By Beachside Management
4 adults
2 bedrooms
3 beds
MapRight across from the beach600m
  • Plunge pool with sea views
  • Two bedrooms and private entrance
  • Steps from Siesta Key Beach
  • Plunge pool
  • Private entrance
  • Outdoor pool
Beachfront resort with family-friendly amenities
FromUS$ 572 /nightSelect
Sea Club II By Beachside Management
The largest option:
4 adults
1 bedroom
2 beds
Map800 yd from City Centre1600 yd from Siesta Beach
FromUS$ 171 /nightSelect
Living The Dream By Beachside Management
The largest option:
6 adults
2 bedrooms
3 beds
Map1.3 mi from City Centre400 yd from Siesta Key Village
FromUS$ 234 /nightSelect
Ten35 Seaside Rentals
Map1.4 mi from City Centre300 yd from
FromUS$ 444 /nightSelect
Palm Bay Club By Beachside Management
The largest option:
5 adults
2 bedrooms
2 beds
FromUS$ 579 /nightSelect
Jamaica Royale Beachfront Tower By Beachside Management
The largest option:
6 adults
2 bedrooms
3 beds
Map600 yd from City Centre1100 yd from Siesta Beach
FromUS$ 1 248 /nightSelect
Siesta Key Condo - On The Water !
4 adults
1 bedroom
2 beds
MapCrescent Beach500m
  • Outdoor swimming pool with stunning views
  • Fishing opportunities nearby for leisure
  • Fully equipped kitchen for family meals
  • Heated pool
  • Barbecue area
  • Fishing access
Waterfront resort with recreational amenities and comfort
FromUS$ 255 /nightSelect
Beach Residences On Siesta, Aka The Hyatt
6 adults
3 bedrooms
2 beds
Map1.5 mi from City Centre300 yd from
FromUS$ 1 060 /nightSelect
Siesta Key Beach - Bari 665 #2
3 adults
1 bedroom
1 bed
Map1100 yd from City Centre300 yd from Siesta Beach
FromUS$ 177 /nightSelect
Beachfront Siesta Key Condo With Pool Access!
MapDirect beach access300m
  • Heated beachfront pool access
  • On-site spa and wellness centre
  • Outdoor dining area with sea views
  • Heated pool
  • Outdoor patio
  • Spa centre
Family-friendly resort with direct beach access and spa facilities
FromUS$ 635 /nightSelect
Siesta Key Beach - Capri 665 #4
4 adults
1 bedroom
1 bed
Map1100 yd from City Centre300 yd from Siesta Beach
FromUS$ 169 /nightSelect
Our House At The Beach 501W By Beachside Management
6 adults
2 bedrooms
3 beds
MapClose to Siesta Key Beach600m
  • Plunge pool with sea views
  • Two spacious bedrooms available
  • Private entrance for added privacy
  • Plunge pool
  • Sea views
  • Outdoor area
Beachfront resort with two-bedroom accommodations
FromUS$ 423 /nightSelect
Siesta Key Escape Ground Floor Steps To Heated Pool And Free Trolley
6 adults
2 bedrooms
3 beds
MapCrescent Beach300m
  • Heated pool just steps from room
  • Rooms with private pool views
  • Free parking for guests available
  • Heated pool
  • Private pool
  • Barbecue area
Family-friendly resort with barbecue facilities and terrace
FromUS$ 233 /nightSelect

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

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