Book directly with us
up to 10% cheaper
than with Booking.com
Check rooms and rates
From2 899US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

5507 Calle Invierno, Siesta Key, Florida, United States, 34236
-
Steps from Siesta Key Beach

Rooms and Amenities

The Lookout is a holiday home featuring 5 separate bedrooms, 5 bathrooms with a walk-in shower and a bath, and 2 living rooms. The kitchen is equipped with a stovetop, refrigerator, dishwasher, and kitchenware. Amenities include air conditioning, a flat-screen TV with streaming services, a washing machine, tea and coffee facilities, and a sitting area. Guests have access to ironing facilities, heating, a terrace, a dining table, patio, and garden furniture. The unit provides 6 beds.

Private Leisure Facilities

This holiday home includes a private pool and hot tub. There is also a barbecue available for guests.

Dining

The Lookout has onsite restaurants.

Location Highlights

The Lookout is located near Siesta Key Drum Circle (1 km), Siesta Key Beach Access 2 (1 km), Sarasota Beach (0.5 km), St. Boniface Episcopal Church Labyrinth (1 km), Siesta Key Craft Festival (1 km), Siesta Key (1 km), Siesta Key Beach (1 km), Edson Keith Estate (3 km), and Siesta Key Beach Access 7 (0.5 km).

Transportation

The Lookout is 20 km from Sarasota Bradenton International Airport.

View all

Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
Five-Bedroom House
2 persons
4500 sq. feet 
1 King-size bed
Shower
Private pool

Calendar of room availability and rates

See current availability and pricing for your dates

Facilities

Amenities are designed to ensure comfort and memorable stays

General

  • No smoking on site
  • Free Wi-Fi
  • Parking
  • Express check-in/ -out
  • Concierge desk
  • Pets allowed
  • Lift
  • Smoke detectors
  • Fire extinguishers

Sports & Fitness

  • Mini golf

Guest Parking

  • Cookware/ Kitchen utensils

Services

  • Grocery shopping service

Dining

  • Outdoor dining area

Children

  • Video games
  • Board games
  • Water slides

Spa & Leisure

  • Outdoor swimming pool
  • Sun loungers
  • Garden area
  • BBQ facilities
  • Jacuzzi

Room features

  • Air conditioning
  • Heating
  • Sitting area
  • Patio
  • Terrace
  • Garden furniture
  • Tea and coffee facilities
  • Dining table
  • Ironing facilities

Bathroom

  • Washing machine

Self-catering

  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV
Show more

The Lookout Villa Location

5507 Calle Invierno, Siesta Key, Florida, United States, 34236
Map view
5507 Calle Invierno, Siesta Key, Florida, United States, 34236
Nearby
Sarasota Beach
1100 ft
402 Beach Rd
Siesta Key Beach Access 7
1200 ft
602 Beach Rd
Public Beach Access 10
1000 ft
Restaurants
Blase Cafe
2300 ft
5263 Ocean Blvd
The Siesta Key Oyster Bar
2600 ft
5238 Ocean Boulevard
The Blase Cafe & Martini Bar
2300 ft
5263 Ocean Boulevard
3.14 Pi Craft Beer & Spirits
2300 ft
5263 Ocean Blvd
Gilligan's Island Bar and Grill
2500 ft
5253 Ocean Blvd
Mojo Risin' Coffee Company
2700 ft
5251 Ocean Blvd
Flavio's Brick Oven and Bar
2700 ft
5239 Ocean Boulevard
Subway
2700 ft
5239 Ocean Blvd Suite B
Gidget's Coastal Provisions
2500 ft
5242 Ocean Blvd
Explore Siesta Key
Local Experiences Near The Lookout
Top Attractions
Activities
Dining
Entertainment
Siesta Key Beach
Siesta Key Beach
14 minutes' walk
Home to soft quartz sand, Siesta Key Beach offers sunbathing, swimming, and beautiful sunsets that draw visitors year-round.
Sarasota Beach
5 minutes' walk
Sarasota Beach features stunning shoreline and calm waters, perfect for families and sunbathers looking for a relaxing day out.
Siesta Key Village
Siesta Key Village
19 minutes' walk
Quaint and vibrant, Siesta Key Village is packed with shops, eateries, and lively nightlife, offering a taste of local culture.
St. Boniface Episcopal Church Labyrinth
St. Boniface Episcopal Church Labyrinth
15 minutes' walk
This peaceful labyrinth invites personal reflection along a scenic path, set amid the serene backdrop of the church's gardens.
Kayaking and Paddleboarding
10 minutes' drive
Local rental shops offer kayaking and paddleboarding to explore coastal waterways. Great for both thrill-seekers and tranquility lovers.
Yoga on the Beach
14 minutes' walk
Participate in rejuvenating beach yoga sessions that provide relaxation while enjoying the sound of waves and fresh ocean air.
Siesta Key Farmers Market
19 minutes' walk
Weekly market featuring local produce, artisanal goods, and crafts offers a taste of the region's farm-to-table culture.
The Siesta Key Oyster Bar
The Siesta Key Oyster Bar
10 minutes' walk
Casual coastal dining with fresh seafood, including signature oysters and a vibrant bar scene with live music nightly.
Blase Cafe
Blase Cafe
9 minutes' walk
Stylish cafe known for its inviting atmosphere and creative cocktails, serves everything from brunch favorites to evening delights.
3.14 Pi Craft Beer & Spirits
3.14 Pi Craft Beer & Spirits
9 minutes' walk
Local craft brewery offering unique beers in a relaxed setting. Perfect for casual dining and enjoying the local craft beverage scene.
Siesta Key Drum Circle
14 minutes' walk
Family-friendly weekly event featuring local musicians and dancers; a lively atmosphere that culminates in a vibrant beach sunset.
Gilligan's Island Bar and Grill
Gilligan's Island Bar and Grill
10 minutes' walk
Fun bar known for its tropical ambience, serving up casual cuisine and cocktails along with entertainment like trivia nights.
Local transportation
City Centre
Siesta Key12 min  ·  3300 ft
Airports
Sarasota Bradenton International Airport (SRQ)28 min  ·  11.3 mi
Charlotte County Airport (PGD)128 min  ·  53.0 mi
Bus
Bus stop2 min  ·  400 ft
Looking for early booking discounts?
Access special offers today
Check Rates
Property information and rules
Check-in
from 16:00-23:59
Check-out
until 10 am
Internet
is available in for free.
Pets
Pets are allowed on request.
FAQs
About The Lookout
What is the distance from The Lookout to the nearest beach?
The Lookout is located just 200 meters from Siesta Key Beach.
Which major airport is closest to The Lookout?
Sarasota Bradenton International Airport is situated 18 km from the property.
What time can guests check in at The Lookout?
Check-in at The Lookout is from 16:00.
What amenities does The Lookout provide for guests?
The Lookout features an outdoor swimming pool, hot tub, free Wi-Fi, and a fully equipped kitchen.
Is parking available at The Lookout?
Public parking is available on-site for free at The Lookout.
What entertainment options are available at The Lookout?
The Lookout offers a mini golf course and video game consoles for entertainment.
How many bedrooms are in the accommodation at The Lookout?
The Lookout has a total of five bedrooms.
What nearby dining options are accessible from The Lookout?
Dining options within 1 km include Lido Key Tiki Bar and other restaurants on Siesta Key.
What features are included in the rooms at The Lookout?
Rooms at The Lookout include air conditioning, a flat-screen TV with streaming services, and a terrace.
What are the check-out times at The Lookout?
Guests must check out by 10:00 at The Lookout.
What type of amenities are available in the bathrooms at The Lookout?
Bathrooms at The Lookout include a walk-in shower, hot tub, and complimentary toiletries.
How far is The Lookout from historical attractions like John And Mable Ringling Museum Of Art?
The Lookout is located 17 km from John And Mable Ringling Museum Of Art.

Next best alternative

Consider them for your next trip.
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Need more options?
Check Top hotels near The Lookout
Island Sun Villa Siesta Key Skyline photo
Mobile-only price

Island Sun Villa Siesta Key

9.5
Perfect2 reviews
85m from property
USD 772USD 694
per night
Sunset Gulf Villa Siesta Key Interior photo
Mobile-only price

Sunset Gulf Villa Siesta Key

9.0
Perfect1 review
113m from property
USD 1716USD 1544
per night
Serenity Beach Condo Siesta Key Exterior photo
Mobile-only price

Serenity Beach Condo Siesta Key

9.3
Perfect3 reviews
118m from property
USD 438USD 394
per night