Vacation rentals in Highland Lakes, Clearwater

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Top-rated vacation rentals in Highland Lakes, Clearwater

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The image showcases a serene beach scene with soft white sand in the foreground, gently lapping waves in a range of turquoise and green hues, under a clear blue sky featuring wispy clouds. The tranquil waters stretch to the horizon.

Home in Indian Rocks Beach

4.99 out of 5 average rating, 166 reviews

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

Welcome to your home away from home. Sand,sun and ocean breeze are waiting for you. Our modern Beach House is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built three story house with nice backyard,heated pool,hot tub and beautiful rooftop. We have everything that you need for bigger groups of families to relax on your Beach vacation.Our Beach House is in a quite neighborhood and still walking distance from restaurants,bars and stor. BTR#2099

Guest favorite

The beachfront condo is shown against a backdrop of clear blue skies and gentle waves. White sand stretches along the shoreline, leading to the building's balconies, which are lined with railings. Refreshing greenery is visible in the distance, contributing to the coastal ambiance.

Apartment in Indian Shores

4.91 out of 5 average rating, 54 reviews

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.

Superhost

A cottage is set amidst vibrant tropical landscaping, featuring palm trees and lush bushes. A stone pathway leads to the entrance, bordered by well-maintained grass and colorful plants, under a clear blue sky, creating a serene outdoor environment.

Apartment in Clearwater Beach

5 out of 5 average rating, 3 reviews

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.

Guest favorite

A cozy outdoor space is illuminated by string lights at night. It features a fire pit with glowing embers, a hammock between two posts, and two seating areas on a grassy patch. A storage unit is visible, adding functionality to the setting.

Guesthouse in Clearwater

4.97 out of 5 average rating, 117 reviews

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.

Guest favorite

A modern kitchen is seen, featuring white cabinetry and stainless steel appliances. The island offers seating with dark chairs, while a range of cooking utensils is organized on the countertop. Bright overhead lighting enhances the space, and a doorway leads to a nearby room.

Home in Largo

5 out of 5 average rating, 9 reviews

Red's Bungalow

Bring your family of 6 or less to this peaceful retreat. This is the best location in the area. Walking distance to the beach, restaurants, shopping centers & groceries. Enjoy the cozy 2 bedroom (6 beds) 1 bathroom that has a living room,kitchen,game room,washer, dryer, green area, porch, patio, and carport. Only 15 minutes away from 2023 US Today's #1 Beach in the South (Clearwater beach) & 30 minutes from 2021 Tripadvisors #1 beach in America St. Pete beach.

Guest favorite

A tidy outdoor area features charming green accents with a bright door leading to a unit. String lights create a soft illumination above a pathway lined with white stones and lush greenery, while a small table and chairs invite relaxation in the pleasant Florida climate.

Apartment in St. Pete Beach

4.8 out of 5 average rating, 311 reviews

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! 🎉🌮

Top guest favorite

A serene beachscape is captured under a clear blue sky, featuring soft white sands that lead to gentle waves. The water transitions from light turquoise to deep blue. A few figures can be seen enjoying the shoreline in the distance, enhancing the peaceful atmosphere.

Apartment in Dunedin

4.98 out of 5 average rating, 238 reviews

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

Guest favorite

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

Home in Palm Harbor

4.93 out of 5 average rating, 54 reviews

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!

Guest favorite

An outdoor seating area features wooden benches arranged in a circular pattern on a stone surface. Colorful potted plants and flowers surround the seating, with a large tree providing shade overhead. Lush greenery is visible in the background, enhancing the tranquil setting.

Condo in Paradise Lakes

5 out of 5 average rating, 18 reviews

Vacation Nude! N5 Studio @ Paradise Lakes

Enjoy Paradise Lakes Clothing Optional Community in this 1sr floor unit. Newly remodeled and upgraded Queen bed unit. Kick your feet up and relax. Cook a full meal to your desire in the fully equiped Kitchenette. Set yourself free in this clothing optional community with access to resort clubhouse/pool (not included/optional).

Top guest favorite

A view of the beach is captured from a balcony, showcasing vibrant turquoise waters and a sandy shore. Sunbathers and colorful umbrellas dot the beach, while charming coastal cottages frame the scene. The image conveys a relaxed atmosphere, with soft ocean waves visible in the background.

Cottage in Indian Rocks Beach

5 out of 5 average rating, 42 reviews

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.