Holiday rentals with beach access in Oldsmar

4.98 out of 5 average rating, 101 reviews

Condo in Clearwater

Lovely Condo minutes from beach & King bed

Kick back and relax in this calm, stylish space.Minutes away from Clearwater Famous Beach.You will be pleased with high ceilings and open floor plan.King size bed in the Bedroom with balcony and 55" smart Tv. Walk-in closet and updated bathroom. Spacious covered patio style balcony. Full-size washer and dryer inside the unit. Fully updated and equipped kitchen. Specious living room with a sleeper sofa that can sleep two quests and 65"smart Tv. Heated outdoor pool, gym, fast wifi internet, cable

4.97 out of 5 average rating, 135 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

4.89 out of 5 average rating, 272 reviews

A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.

Home in Tampa Heights

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

Guesthouse in Tarpon Springs

A comfortable living space includes a dark blue sofa with accent pillows and a coffee table. A dining area with wooden chairs is visible in the background, alongside a fully equipped kitchen. Light-colored cabinets and appliances complement the space.

4.87 out of 5 average rating, 115 reviews

Comfy 1BR Near Beaches & Sponge Docks

Enter your private oasis & enjoy our spacious 1 bd in scenic Tarpon Springs. Relax on the comfy couch or oversized chair. Treat yourself to free snacks, cold water & coffee, tea or hot cocoa w/ the Keurig in the fully equipped kitchen! Enjoy a hot shower or bath. Extra toiletries supplied. Games & books available. Comfortable Queen size bed ensures a great sleep. Only 3 miles from Howard Park Beach & Sponge Docks. Sunset Beach 1.3 miles. Innisbrook Golf Resort 3.9 miles! Private Entrance

4.98 out of 5 average rating, 161 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

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

4.96 out of 5 average rating, 160 reviews

A spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.

Place to stay in Dunedin

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

5 out of 5 average rating, 102 reviews

A private backyard pool area is featured, showcasing a clear blue in-ground pool surrounded by lounge chairs and sunbeds with striped cushions. Lush greenery and potted plants add a tranquil touch, while a shaded umbrella stands at one end for comfort.

Guesthouse in Ozona

Private pool, steps to gulf, fishing, bike trails

Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

4.79 out of 5 average rating, 221 reviews

A studio apartment features a spacious bed adorned with a floral-patterned blanket. A small table is placed in front of the bed, accompanied by decorative items. A kitchenette is visible with sleek cabinetry and modern appliances, and a window provides natural light.

Apartment in Tampa

California

Hi there , this beautiful studio apartment is a very romantic and peaceful place to stay., very central in one of the best areas in Tampa , also near Tampa internacional airpor, Publix , Walmart a few minutes away. The apartment has also a Murphy bed and a laundry both locked for a an extra charge (AS REQUEST FOR AN EXTRA CHARGE), So if you want to have a real good time in a comfortable studio apartment this is the place to stay -Second bed- 30 per day - Landry- ——$ 20

4.99 out of 5 average rating, 263 reviews

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Apartment in Dunedin

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

Apartment in Clearwater Beach

A living area features a navy blue sofa and wooden coffee table, with a decorative fish wall art and plants adding a coastal touch. A television is situated on a sleek white console. Light wood flooring enhances the spacious feel, complemented by a welcoming 'Welcome' sign.

4.85 out of 5 average rating, 170 reviews

Waterfront Courtyard Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

Townhouse in Crystal Beach

A fenced outdoor space features a fire pit surrounded by four blue Adirondack chairs, set on sandy ground. Lush greenery and tall palm trees enhance the tranquil atmosphere, while a grill is visible nearby, providing options for outdoor cooking and relaxation.

4.94 out of 5 average rating, 174 reviews

Relaxing Pond View - Beaches - Bikes - Fire Pit

* Honeymoon/Caladesi Islands (10min) * Pinellas Trail - bike/walk/run * Walk/bike to St Joseph Sound (great for sunsets) * Downtown Dunedin & Tarpon Sponge docks (10min) * Screened patio w/fan & lights * Fenced yard w/grill, view of the pond, a fire pit * Beach chairs, towels and beach toys provided- even some fishing poles for the pier! * 2 adult bikes provided

4.93 out of 5 average rating, 190 reviews

A glass bowl filled with a variety of seashells is placed on a wicker coffee table. The background features a cozy living area with a sofa and warm lighting, creating a relaxed environment.

Home in Tarpon Springs

Historic Downtown Tarpon Springs Hidden Gem

Come be our guest in beautiful Tarpon Springs, Florida! Our charming home welcomes you to rest and be comfortable as you enjoy this lovely and unique area. It is your “home away from home” as you explore all the area’s attractions. Greek Town, Downtown Tarpon, Sponge Docks, beaches, hiking parks, craft beer/wine/spirits, and the Pinellas Trail (just to name a few).

Popular amenities for Oldsmar Accommodation with Beach Access

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Apartment in Indian Rocks Beach

A roadside view of a pink cottage features large windows inviting natural light. A white door is visible, with two chairs placed on the gravel-covered area. Surrounding greenery enhances the outdoor space, while a parking lot provides convenient access.

4.95 out of 5 average rating, 209 reviews

Vintage Florida Beach Efficiency

Apartment in Madeira Beach

A direct view of the Gulf shoreline is visible from the balcony, showcasing a sandy beach with beach chairs and umbrellas. A private pool is located below, surrounded by a patio area with several lounge chairs, creating an inviting setting for relaxation.

4.9 out of 5 average rating, 102 reviews

Welcome to Gulf-Front Paradise!

Apartment in Historic Kenwood

A charming two-story bungalow surrounded by lush greenery and outdoor seating. The entrance features a set of steps leading to a wooden porch, framed by large windows that invite natural light. The yard includes various plants, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 398 reviews

Historic Kenwood Getaway

Apartment in Indian Shores

A spacious living area is furnished with two comfortable leather sofas and a wooden side table. A large flat-screen TV is positioned nearby. Natural light floods the room through expansive glass doors leading to a balcony, with ocean views visible in the distance.

4.92 out of 5 average rating, 191 reviews

Beach Front Condo!

4.97 out of 5 average rating, 598 reviews

A modern living area features a stone accent wall, complemented by a large clock. Two comfortable sofas with black and red cushions surround a coffee table. A dining table for four is visible, along with a well-equipped kitchen in the background, enhancing the spacious feel.

Apartment in Tampa

Cozy 2 BR "Rustic Chic" Hyde Park nook | KING bed

Apartment in Independence Square

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

4.96 out of 5 average rating, 181 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Apartment in Pinellas Park

The living area features a wall-mounted television, a glass coffee table, and a comfortable sofa. A dining table with two chairs and an extra chair are positioned near a window. Soft lighting is provided by a pendant light and ceiling fan.

4.86 out of 5 average rating, 188 reviews

Cozy little getaway

Apartment in Indian Rocks Beach

A sandy pathway leads from a wooden deck to the beach, framed by wooden railings. The expansive shoreline is visible, with gentle waves lapping at the shore under a bright blue sky. Beachgoers can be seen enjoying the sun and water in the distance.

4.78 out of 5 average rating, 101 reviews

20 Steps To The Beach | Private 1BR Unit On Beach

Holiday House Rentals with beach access

4.93 out of 5 average rating, 141 reviews

A spacious living area features a large sectional sofa adorned with various decorative pillows. A light-colored coffee table is positioned in the center, complemented by a decorative basket. Natural light filters through two window blinds, creating a bright and inviting environment.

Home in Dunedin

Ocean Sunsets & Downtown Biking Trails

4.96 out of 5 average rating, 102 reviews

An outdoor deck area is furnished with a glass-top dining table and four chairs, surrounded by vibrant potted plants. Lounge seating is positioned to one side, offering a relaxed space. The house is visible in the background, featuring a light exterior and a stylish mirror on the wall.

Home in Tarpon Springs

The Modern Farmhouse

4.79 out of 5 average rating, 133 reviews

Home in Clearwater

Heated Pool Beach House | Hot Tub, Fire Pit, Games

4.86 out of 5 average rating, 240 reviews

A covered patio area is furnished with two blue chairs and a small round table. The space is enclosed by a wooden fence and features a grassy area along with gravel, creating a relaxed outdoor setting.

Home in Tampa

Boho Villa

4.79 out of 5 average rating, 136 reviews

A covered swimming pool area features a clear and inviting pool, surrounded by a spacious patio with tiled flooring. Large glass doors allow natural light to flood the space, while lounge chairs are positioned nearby, offering a comfortable spot to relax.

Home in Dunedin

The House of Relaxation

4.92 out of 5 average rating, 139 reviews

A light-filled living area is furnished with a comfortable grey sofa and two wooden chairs. A round coffee table sits in the center on a natural fiber rug. A wall-mounted TV displays a scenic view, while large windows with blinds allow natural light to enter.

Home in Largo

12 Mins to Beach | Patio&Grill | Fenced Yard

4.93 out of 5 average rating, 122 reviews

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

Home in Palm Harbor

Lakefront home near beaches w/ waterview, pets ok

4.83 out of 5 average rating, 115 reviews

The spacious living room is adorned with a large blue sectional sofa and a stylish yellow accent chair. A round coffee table sits on a decorative rug, while a smart TV is positioned on an entertainment center. Natural light enters through the blinds of the windows, illuminating the room.

Home in Tampa

🗝Home in Tampa Bay for a cozy stay☀️

Holiday condos with beach access

Condo in Indian Rocks Beach

The inviting living space is furnished with a blue sofa, two armchairs, and a white coffee table. A starfish-patterned rug adds a nautical touch. Natural light filters through window blinds, illuminating the area. The open layout connects to the kitchen, visible in the background.

4.97 out of 5 average rating, 128 reviews

Renovated Condo! Across the Street From The Beach

4.98 out of 5 average rating, 200 reviews

A vibrant, themed living area features colorful hanging lamps and intricate wall decorations. Lush greenery is present, alongside a mixture of patterned seating arrangements. Large glass doors open to a balcony, allowing natural light to fill the space and offering a view of the outdoors.

Condo in Tampa

Tiki Themed Waterfront Condo on Tampa Bay

4.9 out of 5 average rating, 180 reviews

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

Condo in Treasure Island

Waterside Studio in the heart of TI, walk to beach

4.75 out of 5 average rating, 259 reviews

A wooden pier extends over smooth waters, bordered by rocky outcrops. The sky is painted in vibrant hues of orange and purple as the sun sets on the horizon, casting a tranquil glow across the scene.

Condo in Tampa

Rocky Point paradise

4.94 out of 5 average rating, 133 reviews

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages

4.8 out of 5 average rating, 103 reviews

Two wicker chairs with cushions are positioned around a small table on a balcony overlooking the beach. The expansive view reveals the Gulf of Mexico and a clear sky with scattered clouds. Beachgoers can be seen in the distance enjoying the shoreline.

Condo in Indian Shores

Casa de B.O.B ... Best on Beach

4.85 out of 5 average rating, 112 reviews

Condo in Tampa

Waterfront Condo with Heated Swimming Pool