Florida Premier Rentals

Photo: John Simpson, CC BY 3.0

The Anchorage is a gated condominium complex on Siesta Key in Sarasota, Florida, on the Intracoastal Waterway with a private gate across Midnight Pass Road to Crescent Beach, offering two- and three-bedroom condos, a large heated pool, tennis and pickleball courts, and a boat dock and kayak launch.

Inside the resort

What is on site at Siesta Key

A Gulf beach stay, not a park base

The Anchorage is a different kind of stay from the rest of our resorts. It is a single gated condominium building on Siesta Key, on the bay side of Midnight Pass Road, backing onto the Intracoastal Waterway near the Stickney Point Bridge. Instead of a private house, you rent a two-bedroom condo of over 1,200 square feet or a three-bedroom of around 2,400, reached by elevator, and the beach is across the road: a private access gate leads straight onto Crescent Beach.

Siesta Key is the draw. Siesta Beach, about a mile and a half north, is famous for sand that is nearly 100% quartz crystal, and it has been named the number one beach in the United States several times, most recently by Tripadvisor in 2025. At the south end of Crescent Beach, Point of Rocks is the largest rock formation on Florida's Gulf Coast, and it features in Visit Sarasota's snorkelling guide. The free Siesta Islander trolley runs between Siesta Key Village and Turtle Beach every day, so a car can stay parked for most of the week.

Walt Disney World is roughly two hours away by car, which makes a day at the parks possible but not something to plan a week around. If the parks are the point of the holiday, our Orlando resort communities are a far better base, and some guests split a trip between the two.

Pool and waterfront

  • Heated pool

    Described by the building's rental office as one of the largest heated swimming pools on Siesta Key.

  • Boat dock and kayak launch

    On the Intracoastal Waterway, with kayak racks. Docking a boat carries a small fee — ask the rental office.

  • Fishing and fillet station

    At the waterfront, for anyone fishing from the dock.

Courts and games

Game equipment is free to borrow; sign it out at the rental office.

  • Tennis

    Lighted courts, with equipment available.

  • Pickleball

    Courts on site, with equipment available.

  • Shuffleboard

    Lighted courts.

  • Basketball and cornhole

    A basketball hoop and cornhole for an easy afternoon.

  • Exercise room

    Inside the building.

Around the building

  • Outdoor kitchenette

    With two propane grills, for cooking outside.

  • Laundry on every floor

    Coin-operated washers and dryers at both ends of each hallway.

  • Two elevators

    Serving every floor of the building.

Siesta Key at a glance

Siesta Beach sand
Nearly 100% quartz crystal
Siesta Beach
Lifeguard-patrolled, open 6am–10pm, over 900 free parking spaces
Point of Rocks
South end of Crescent Beach; the largest rock formation on Florida's Gulf Coast
Free trolley
Siesta Islander, 8am–10pm daily, Siesta Key Village to Turtle Beach
Siesta Key Village farmers market
Sundays, 8am to noon

Know before you go

Practical details for Siesta Key

Gated entry
Gated, with key or code entry at every access pointArrival and access details come with your booking confirmation.
Beach access
Private gate across Midnight Pass Road to Crescent BeachThe path runs between the Siesta Sun and The Breakers, with the gate at the end.
Minimum stay
Often 7 nightsThe building's rental office books week-long minimums. The rule for your condo is confirmed when you book.
Pets
Not allowedService animals with documentation are accepted; emotional support animals are not, according to the building's rental office.
Age
Lead guest 25 or olderThe building's rental office requires the person reserving to be at least 25.
Parking
On siteListings differ on covered or uncovered spaces, and cars may need registering at the front office. We confirm it for your condo.
Laundry
Coin-operated, on every floor
Location
6415 Midnight Pass Road, Siesta Key, Sarasota, FL — near the Stickney Point Bridge

Frequently asked questions

Where is The Anchorage on Siesta Key?

The Anchorage is at 6415 Midnight Pass Road on Siesta Key, Sarasota, Florida, near the Stickney Point Bridge. The building sits on the bay side of the road, backing onto the Intracoastal Waterway, with Crescent Beach directly across the road.

Does The Anchorage have beach access?

Yes. The complex has a private beach access gate directly across Midnight Pass Road, reached by a path between the Siesta Sun and The Breakers. It opens onto Crescent Beach, a walk of a few minutes from the building.

How far is The Anchorage from Disney World?

About 122 to 125 miles to the Walt Disney World park gates, or roughly two hours and fifteen minutes by car without traffic. A day trip is possible, but if the parks are the main reason for the holiday, a home in one of our Orlando resort communities is a much better base.

What amenities does The Anchorage have?

A large heated pool, lighted tennis and shuffleboard courts, pickleball, a basketball hoop, cornhole, an exercise room, an outdoor kitchenette with propane grills, and on the waterfront a boat dock, a kayak launch with racks and a fishing and fillet station.

Is The Anchorage a gated complex?

Yes. There is a gate at the front of the property, and every access point uses key or code entry. Arrival and access details are sent with your booking confirmation, so there is nothing to arrange before you get there.

Are pets allowed at The Anchorage?

No. According to the building's rental office, pets are not allowed, though service animals with proper documentation are accepted; emotional support animals are not. Ask us before booking if you are travelling with a service animal, so the paperwork is in place.

How big are the condos at The Anchorage?

The two-bedroom condos are over 1,200 square feet and the three-bedroom condos are around 2,400 square feet, according to the building's rental office. The building has two elevators, and coin-operated laundry at both ends of the hallway on every floor.

How far is The Anchorage from Siesta Beach?

About 1.7 miles, roughly seven minutes by car. Siesta Beach is known for sand that is nearly 100% quartz crystal, is patrolled by lifeguards and has over 900 free parking spaces, although Crescent Beach, right across the road, is the closer beach.

Is there a trolley on Siesta Key?

Yes. The Siesta Islander trolley is free and runs from 8am to 10pm every day of the year between Siesta Key Village and Turtle Beach, along Midnight Pass Road. It makes a car unnecessary for most trips on the island.

Can I bring a boat or kayak to The Anchorage?

The complex has a boat dock and a kayak launch with racks on the Intracoastal Waterway, and a fishing and fillet station. Docking a boat carries a small fee set by the building's rental office, so ask us before you travel.

What is the closest airport to The Anchorage?

Sarasota Bradenton International Airport is about 12 miles away, roughly half an hour by car. Tampa International Airport is about 70 miles away, around an hour and twenty minutes without traffic, and usually has more flight options.

Book direct

Let's find your Siesta Key home

Karen, Yvonne and Amalia know these homes personally. Tell us your dates and party size and we'll shortlist the right ones — no platform fees, flexible payments.

  • Transparent pricing — no hidden platform fees
  • Flexible payment plans on every booking
  • Homes inspected by us between each stay
  • One family, three names, always reachable

Siesta Key

Check dates