Holiday rentals with beach access in Oldsmar

4.98 out of 5 average rating, 100 reviews

Apartment 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

Apartment 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.

Superhost

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

4.89 out of 5 average rating, 268 reviews

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).

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, 157 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.

4.98 out of 5 average rating, 144 reviews

The bedroom features a spacious bed adorned with patterned pillows, complemented by two bedside tables with decorative lamps. Artistic wall frames in muted tones enhance the ambiance. A soft glow is provided by lighting, and sheer curtains allow natural light to filter in.

Apartment in Clearwater

Cozy condo, main floor, min to beach, heated pool

This amazing condo is a 5-minute drive to the beautiful Clearwater Beach, as well as bars, restaurants, and many other attractions. The unit is situated in a lovely, resort-style gated community that features a clubhouse, heated pool, gym, Wi-Fi, and complimentary parking. This perfect retreat offers full privacy as each room provides separate access to the bathroom. The condo is on the main floor, offering easy access in and out, and includes a laptop-friendly workspace. Just come and relax!

4.89 out of 5 average rating, 161 reviews

Gulf Side Florida Charm 1/1 Condo 60 Steps To Sand

Step back in time at Postcard Paradise, a charming beachside cottage that captures the magic of Old Florida. Nestled just steps from the shore, our eclectic retreat feels like living inside a vintage postcard. Sun-faded colors, and tropical murals set a nostalgic mood, while modern comforts keep things easy and relaxed. Each cozy room is filled with hand-picked decorations, breezy linens, and quirky coastal finds, creating a one-of-a-kind space where every corner tells a story.

5 out of 5 average rating, 101 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.

Guest house 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.

Apartment in Indian Rocks Beach

A spacious balcony is bordered by tall palm trees, offering a view of the calm Gulf of Mexico and white sand beach. The clear blue sky complements the serene ocean, creating a tranquil setting for relaxation.

4.89 out of 5 average rating, 102 reviews

Gulf-View 2BR/2BA Beach Condo!

This Indian Rocks Beach Gulf Front Hamilton House building is located directly on unique Clearwater- St.Pete white sand beach with private beach access and heated pool, washer and drier in the unit. Our 3rd floor 1100 sq. feet 2 bedroom condo #207 offers a spacious balcony bordered with palm trees with northerly nice side view of the Gulf of Mexico and white sand beach that goes on for miles. Two assigned parking spaces (one under the building and second uncovered).

Apartment in Indian Rocks Beach

A shaded lounging area features a comfortable chair with a patterned cushion, facing a serene waterfront view. In the background, a dock extends into the calm water, surrounded by lush greenery and decorative plants.

4.96 out of 5 average rating, 127 reviews

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam king bed & secured safe.

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.

Flat 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

4.79 out of 5 average rating, 164 reviews

Home in Tarpon Springs

Mins to Beach/Studio Home/walk to dwtn/FreeParking

✨ Beautifully remodeled studio in the heart of Tarpon Springs. Just an 8-minute drive to the beach, this cozy retreat was thoughtfully designed with comfort in mind. Featuring a comfy queen bed and a bright, welcoming interior, it’s the perfect spot to relax after exploring the Sponge Docks, downtown, and nearby attractions.

Popular amenities for rentals with beach access in Oldsmar

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Flat 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, 207 reviews

Vintage Florida Beach Efficiency

4.94 out of 5 average rating, 108 reviews

Flat in Clearwater Beach

Anchors UP #2, WALK to Beach, 1 bed/1 bath apt.

4.97 out of 5 average rating, 594 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.

Flat in Tampa

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

4.92 out of 5 average rating, 132 reviews

The living area features a spacious couch and a flat-screen television, with a soft area rug anchoring the space. Floor-to-ceiling sliding glass doors provide sweeping ocean views and direct access to the private balcony, creating an inviting connection to the beach.

Flat in Indian Shores

Ocean Front Condo!

Flat 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, 180 reviews

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

4.86 out of 5 average rating, 187 reviews

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.

Flat in Pinellas Park

Cozy little getaway

Flat in Indian Rocks Beach

An aerial view captures the serene coastline and vibrant community of Indian Rocks Beach. The expanse of blue water meets the sandy shore, with buildings and residences lined along the beach. Green parks and water channels are visible, enhancing the coastal atmosphere.

4.96 out of 5 average rating, 117 reviews

Cozy coastal grandmother condo, walk to the beach!

4.89 out of 5 average rating, 244 reviews

A modern dining area features a round glass table set for six, surrounded by white chairs. A unique blue chandelier hangs above, while large windows offer a view of the water. The kitchen area is equipped with white cabinetry and stainless steel appliances.

Flat in Clearwater Beach

Waterfront Modern Chic #1 Clearwater Beach

House rentals with beach access

4.94 out of 5 average rating, 139 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

4.99 out of 5 average rating, 194 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

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

4.98 out of 5 average rating, 143 reviews

A cozy open-concept living area features a spacious light-colored sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, positioned on a striped area rug. Elegant pendant lights hang above a large kitchen island with a granite countertop, contributing to a welcoming ambiance.

Home in Largo

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

4.93 out of 5 average rating, 121 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

4.82 out of 5 average rating, 114 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☀️

4.91 out of 5 average rating, 409 reviews

A spacious outdoor entertainment area features a tropical saltwater pool surrounded by a screened enclosure. Colorful loungers in vibrant pink and green are positioned near the pool, complemented by a dining table. A shaded area offers comfort for relaxing in the sun.

Home in St. Petersburg

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Home in Indian Rocks Beach

A spacious kitchen is presented with warm wooden cabinetry and modern stainless steel appliances. Light-colored granite countertops enhance the area. A large island provides additional workspace, while natural light fills the room from nearby windows, contributing to a bright cooking environment.

4.93 out of 5 average rating, 106 reviews

A- BEACH HOUSE- 3 MIN WALK TO SAND

Apartment rentals with beach access

A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.

4.97 out of 5 average rating, 113 reviews

Relax in a Newly Renovated Beach Front Paradise

A waterfront view showcases the community pier lined with palm trees, providing access to the Intracoastal waterway. The nearby building features balconies and patio furniture under blue umbrellas, enhancing the leisure atmosphere. Multiple docks extend into the clear water, inviting relaxation.

4.97 out of 5 average rating, 112 reviews

Blue Sea Renity -Steps to Beach| Heated Pool

Apartment in Madeira Beach

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

4.99 out of 5 average rating, 218 reviews

Lux Condo w/ 2 balconies, Ocean & Marina views

Apartment in St. Petersburg

A sunset is captured over the intercoastal waterway, with warm hues reflecting on the water's surface. Silhouettes of palm trees line the foreground, while distant markers indicate the waterway's navigation. The scene conveys a tranquil ambiance, enhanced by the fading light.

4.91 out of 5 average rating, 180 reviews

Heron's Hideaway- Studio by the bay!

4.95 out of 5 average rating, 104 reviews

A heated swimming pool is surrounded by neatly arranged loungers, with palm trees providing shade. A clear sky and vibrant sunset colors reflect on the water's surface. The pool area is enclosed by a black fence, ensuring a private and relaxing environment.

Apartment in Largo

Boho Beach Condo

4.75 out of 5 average rating, 257 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.

Apartment in Tampa

Rocky Point paradise

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.

4.94 out of 5 average rating, 133 reviews

Tropical Beachfront Penthouse-Beach Cottages