Vacation rentals in Carrollwood, Greater Carrollwood

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Top-rated vacation rentals in Carrollwood, Greater Carrollwood

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Guest favorite

A boat glides across the shimmering water as the sun sets behind the Tampa River Center, with warm lights reflecting off the surface. Palm trees are visible in the background, and the tranquil scene captures the evening ambiance of the area.

Townhouse in Riverview

4.86 out of 5 average rating, 114 reviews

Your New Townhome Awaits!

Osprey Lakes New Townhome 3/2 Bathroom breathtaking clean & New. Close to DownTown Tampa, Apollo Beach, Naples, Sarasota, and Orlando- or even Miami! Just come on Down! you are minutes away from HardRock Casino, Amusement Parks, Tampa International Airport. Golf Courses, Channel Side, I4 to Disney, all Beaches & Paradise! Let me host your stay, you will be delighted. *****Location Location Location***** 10 MileRadious CHANNELSIDE SOUTHTAMPA APOLLO TAMPABAY Ruskin Brandon YBOR SARASOTA

Top guest favorite

Bungalow in Oldsmar

4.98 out of 5 average rating, 103 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top guest favorite

An inviting living area features a wall-mounted television and a decorative wooden sign reading 'Salt Life.' A spiral staircase leads to an upper level, while a palm leaf-patterned rug complements the warm wooden flooring.

Villa in Safety Harbor

5 out of 5 average rating, 134 reviews

Villa Key West "Villas by Christine"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

Guest favorite

The image features a serene shoreline at sunset, with the sun casting a warm golden glow across the water. Silhouetted figures can be seen by the water's edge, surrounded by rocks and sandy beach. Gentle waves lap against the shore, creating a tranquil atmosphere.

Home in Holiday

4.93 out of 5 average rating, 14 reviews

Charming Sunshine Retreat

Welcome to our charming retreat in the heart of Florida! This cozy Airbnb is perfectly situated for your convenience, with easy access to shopping, dining, and all the amenities you could desire. Nestled just a stone's throw away from the stunning beaches that Florida is renowned for, you'll find yourself immersed in coastal bliss. Book your stay at our centrally located Florida retreat and discover the perfect balance between relaxation and excitement. Your dream vacation starts here!

Top guest favorite

A bright and airy dining area features a round wooden table surrounded by four light-toned chairs. A decorative centerpiece rests on the table, while large windows allow natural light to fill the space, blending seamlessly with the adjoining living room.

Home in Seminole

5 out of 5 average rating, 61 reviews

Coastal Getaway~Spacious~ 5 min to Madeira Beach!

Relax at our spacious, elegant, coastal getaway home and enjoy its proximity to the Top 25 Beaches in the US. Madeira Beach (2.3 miles), voted #9 and St. Pete Beach voted #1 (7.7 mi ) in 2021. Modern kitchen provides abundant space for meals and entertainment. Dine out or Door dash, we are centrally located near restaurants and shoppings area. FL Botanical Garden 5mi, Pinellas Bike Trail 1 mi. Walsingham, Lake Seminole, and Veterans Memorial parks all within 4 miles.

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

4.98 out of 5 average rating, 121 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.

Top guest favorite

Apartment in Dunedin

4.99 out of 5 average rating, 238 reviews

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Superhost

An open living area features a gray sectional sofa facing a wooden coffee table. Bright artwork adorns the walls, complemented by stylish bar stools at the kitchen island. Modern fixtures and natural light create an inviting space, with light-colored flooring extending throughout.

Home in Pinellas Park

4.81 out of 5 average rating, 69 reviews

Beautiful Retreat Haven/ 7 miles to beach

Indulge in the perfect vacation getaway with our splendid 3-bedroom, 2-bathroom listing. This beautifully renovated property offers the allure of an outdoor fire pit, a recent brand new remodel, and the convenience of WiFi and smart TVs throughout the entire house. Nestled in a tranquil and quiet neighborhood, we're just 7 miles away from the sun-kissed beach, offering you the best of both worlds - peaceful relaxation and coastal adventure.

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, 240 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

Home in Dunedin

5 out of 5 average rating, 7 reviews

Welcome to Cozy Coastal Cottages of Dunedin #1-2

Welcome to Cozy Coastal Cottages of Dunedin #1-2 ⭐⭐⭐⭐⭐ Words cannot describe this cozy, beautiful, and fully remodeled vacation rental within walking distance of downtown Dunedin! This listing is for an entire building, which consists of 2 separate units, each one is 2 bedrooms & 2 bathrooms. This listing sleeps up to 10 guests! Also, on the same lot, we have another listing, available to sleep 18 guests!

Top 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, 59 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).