Holiday rentals in Highland Lakes, Clearwater

Breathtaking Accomodations

Newly remodeled! This 3 bedroom 2 bath beach condo offers an expansive view of the white sand and gulf waters. Make memories in the bright & breezy kitchen, dining & family room with ocean view and balcony seating. Appreciate private beach & pool to relax & recharge while the sunshine and ocean breeze are perfect combination for outdoor fun. Premier host offers 5-star service along with all the amenities including SMART TVs, WiFi, reserve parking, heated pool, beach chairs & towels.

LAZY LEMON COTTAGE 2 pools steps from the beach!!!

Our 2 bedroom, 1 bath vacation rental is part of a 7 cottage resort located on the quiet Cyprus Avenue behind the Chapel By The Sea Church. These beautiful homes are landscaped together in a tropical garden, with palm trees and room for 2 heated pools, all very peaceful and private. We are 2 block 2 minute walk to the beach. Unlike most residential homes we are very close to the shops, and restaurants. Our cottages are cleaned to the highest standards for your families health.

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Make your vacation relaxing, fun and easy! - Kick back in the hammock or have some coffee with loved ones in the peaceful private backyard. - Take the 12 minute drive to the beach with the provided boogie boards, chairs and sand toys. - Take a walk or bike ride on the gorgeous Pinellas Trail. You'll also find some of the best coffee, food and ice cream on the way. -Golf courses close by. This is a separate unit that shares a driveway and parking area with the front house.

Cactus-Themed Retreat,Walk to Beach<1 mile: 4plex

🌵Fiesta Siesta – Where Every Day Feels Like a Party!🌴 Feed me tacos and tell me I’m pretty—because life’s too short for anything less! Welcome to Fiesta Siesta, a fun, vibrant escape just steps from Upham Beach in sunny St. Pete Beach. One of four uniquely themed units in a gated complex, this playful retreat is decked out in a vibey cactus theme that’s all about fiesta and siesta—because, why choose? Book now and let the fiesta begin! 🎉🌮

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Private pool, Golf Cart, Completely Renovated!

Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!

Beachy Paradise

FULLY REMODELED INTERIOR AND EXTERIOR 01/2025!! Your perfect getaway cottage! Only 100 steps away from one of the best beaches around. Shops and restaurants all within walking distance. Tennis and basketball courts are across the street for some good exercise! BTR #1955

Upper Deck prime area no condos/crowds

The location is one of the best on the West Coast. I’ve had only 5 stars from my guests. Our places are fully stocked and very clean. This whole property is award winning! Plus, we attract artists -Also our cottages have appeared on many calendars, cards and artists' canvas.

2 Bed Clearwater Vacation Condo.

This vacation condo is perfect for families and couples who want an affordable, resort-like stay in Florida. The condo is only 3 miles away from CLEARWATER BEACH, named BEST BEACH of 2016 in the US by TripAdvisor. The condo is on the 3 FLOOR . NO ELEVATOR