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Stay here. Play here.

Vacation Planning

Plan your Clearwater vacation with a local.

From dolphin tours to the best seafood spots, our team builds personalized itineraries — because planning is part of what we do.

Build Your Trip

Choose your Clearwater pathway.

Each pathway connects you to the right rentals, activities, and local recommendations.

Family Beach Week

Spacious suites for four, kid-friendly activities, and a local itinerary built around Pier 60 and dolphin tours.

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Couples' Waterfront Escape

Intimate studios, sunset dolphin cruises, and a private jet ski tour for two on the Gulf.

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Adventure Weekend

Jet ski tours, kayak paddles, paddleboarding, and a houseboat stay on the Intracoastal.

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Pet-Friendly Getaway

Waterfront rentals that welcome your dog, plus bike rides and beach walks together.

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Clearwater Without a Car

Walkable, bikeable stays with the Jolly Trolley and complimentary beach cruisers.

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Group & Multi-Rental

Booking multiple properties for a family reunion or group celebration? We coordinate it.

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Local Concierge

What our team helps with.

  • Choosing the right waterfront rental
  • Arranging jet ski tours & watersports
  • Recommending restaurants and sunset spots
  • Building family-friendly itineraries
  • Coordinating multi-property group bookings
  • On-site support throughout your stay

Stay here. Play here. Experience Clearwater like a local.

Our team works closely with guests to tailor experiences — whether it's arranging a dolphin-watching cruise or recommending the best local seafood spots.

Plan With UsArea Guide

Sample Itinerary

A perfect Clearwater day.

Morning

Bike & breakfast

Grab a complimentary cruiser and ride to a beachfront cafe.

Afternoon

Jet ski dolphin tour

Carve across turquoise waterways with Idle Speed Watersports.

Evening

Sunset at Pier 60

The nightly sunset festival, then dinner at Frenchy's.

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