Waterfront vacation rentals in Oldsmar

A screened-in patio features a heated swimming pool, surrounded by white decking. The pool offers a view of the canal with palm trees and neighboring properties beyond. The tranquil outdoor space is complemented by a backyard with swings and a dock visible in the background.

4.93 out of 5 average rating, 152 reviews

Waterfront Resort with HEATED POOL!

🌴 Escape to this luxurious waterfront retreat in the peaceful community of Tampa Shores ☀️ an outdoor lover’s dream with direct bay access to the Intracoastal. Enjoy fishing, dolphin 🐬and manatee 🌿🦭 watching, or simply relax on your private dock surrounded by nature. Start your morning with coffee ☕️ on the second-story screened patio, offering breathtaking canal views and overlooking the heated private swimming 🏊‍♀️ pool below. The possibilities are endless! Lay back and enjoy your stay!

4.99 out of 5 average rating, 103 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

+Spacious family retreat on lake +Free heated pool +Huge last-minute discounts +Big deck, BBQ, dining & firepit +Private backyard lakefront +3 bedrooms, 1 king, 1 queen, 2 twin +3 full baths +Easy to cancel +Pet friendly +Fishing +Games +Quiet serene safe +5 minutes to Gulf sunsets +5 min to Sims Park +20 min to Tarpon Springs +39 min to Tampa airport +50 min to Busch Gardens +5 min to restaurants +Fully equipped kitchen +Free parking & garage +Washer-Dryer +Work area +Hi-speed WIFI +Smart TVs

4.96 out of 5 average rating, 135 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

4.96 out of 5 average rating, 205 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

4.93 out of 5 average rating, 132 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

Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

4.96 out of 5 average rating, 111 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

Paradise!Renovated waterfront pool home.Sunsets!

Sunsets to die for! Remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard & and spotting dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops. New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys. Fishing rods.Bonfire pit.Grill.Heated pool for a fee. Portable crib,stroller, high chair. Come,relax&enjoy No hurricane damage!

Condo in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.91 out of 5 average rating, 488 reviews

Amazing views on beachfront

This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.

4.96 out of 5 average rating, 119 reviews

A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.

Farm stay in Odessa

Cabin 3 - Nasturtium Nest

Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay. We look forward to seeing you on the Farm!

4.89 out of 5 average rating, 122 reviews

Home in Clearwater

Bday+Events•HotPool+Projector•10min2Beach

Lakefront 5BR with a half-acre fenced backyard - 10 min to Clearwater Beach: - 200" cinema screen at the pool's edge, movies over the water after dark - Heated pool, fire pit, hammock, sun loungers, lawn games - Event deck under string lights, fits rented tables and chairs - Jetted spa tub in the master: floor and side jets, LED, built-in speakers - 4 king bedrooms + a bunk room, so nobody sleeps on a pullout - Vaulted ceilings, marble tile, new AC | Pets welcome | Self check-in

A well-maintained private pool area is enclosed with a screened lanai, offering protection from insects. The pool's clear water reflects the blue sky with scattered clouds, while the surrounding patio features an outdoor table, creating an inviting space for relaxation and enjoyment.

4.88 out of 5 average rating, 117 reviews

Tampa Getaway Pool Home

Escape to paradise in this stunning and spacious 4 bedroom home with a private pool. Inside, you'll find endless entertainment options with smart TVs, a pool table, foosball table, indoor basketball arcade, and dart game. Centrally located, this home is just a short drive to some of Florida's top attractions including golf courses, the airport, Raymond James Stadium, Busch Gardens, the aquarium, downtown, the convention center, and popular beaches.

4.98 out of 5 average rating, 270 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe.

5.0 out of 5 average rating, 169 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Popular amenities for Oldsmar waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.9 out of 5 average rating, 105 reviews

A pool area is presented featuring a spacious swimming pool surrounded by lounge chairs and colorful umbrellas. A deck with pavers leads to the water, while palm trees and a building provide a backdrop, contributing to a relaxing atmosphere.

Apartment in Tampa

Sunset Paradise

Apartment in Clearwater Beach

A bright living area features a comfortable sectional sofa adorned with decorative pillows. A dining table sits beside large windows, allowing natural light to fill the room. The space is complemented by light-colored walls and stylish light fixtures.

4.89 out of 5 average rating, 129 reviews

NEW! Amazing Beach & Sunset Views! Fully Renovated

4.93 out of 5 average rating, 107 reviews

A covered patio features four comfortable wicker chairs surrounding a glass-top table. Large windows provide views of palm trees and the sunset over the water, creating a serene outdoor space for relaxation.

Apartment in Clearwater

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Apartment in Clearwater Beach

A modern dining area features a round glass table set for six, accompanied by stylish white chairs. Large sliding glass doors provide a waterfront view, while a vibrant artwork hangs on the wall. A contemporary light fixture adds a playful touch to the space.

4.88 out of 5 average rating, 266 reviews

Waterfront 2BR Escape Walk to Beach Pool Sleeps 6

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.

4.93 out of 5 average rating, 230 reviews

Direct Beachfront Condo, Ocean balcony view!

4.8 out of 5 average rating, 213 reviews

An outdoor space features a wood-burning fire pit surrounded by a cozy seating area. A glass table holds a wine glass, and a calm river reflects the evening sky, dotted with trees along the shoreline. The tranquil atmosphere invites relaxation beside the water.

Apartment in Tampa

Kayaks & Firepit Mins to Dwntwn!

Apartment in Tarpon Springs

An aerial view showcases a modern two-story house surrounded by water and greenery. A private boat dock is positioned in the foreground, along with a manicured lawn featuring a putting green and colorful kayaks. Solar panels are visible on the rooftop.

5.0 out of 5 average rating, 107 reviews

Waterfront Studio Apartment w/access to Gulf

Apartment in Clearwater Beach

A paved pathway leads to a wooden dock extending over calm waters. Lush green grass borders the walkway, with vibrant plants adding color to the serene outdoor setting. A clear blue sky is visible, enhancing the tranquil atmosphere by the water.

4.98 out of 5 average rating, 153 reviews

Anchors UP #4, WALK to Beach; WATER VIEW; Sleeps 8

Waterfront house rentals

4.92 out of 5 average rating, 171 reviews

A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.

Home in Tampa

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

4.92 out of 5 average rating, 121 reviews

An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.

Home in Holiday

Lakefront Paradise with Heated Saltwater Pool

4.94 out of 5 average rating, 116 reviews

The exterior of a two-story mansion is showcased, featuring elegant arched windows and a red-tiled roof. A stairway leads to the entrance, while a decorative fountain is positioned in front. Lush landscaping surrounds the home, enhancing its inviting appearance.

Home in Tampa

** Tampa Riverfront Mansion ** Pool / Hot Tub / ..

4.93 out of 5 average rating, 106 reviews

A screened patio surrounds the inviting pool, providing views of the waterfront. Sunlight glimmers on the clear water, and grassy areas border the pool deck. Nearby boat docks are visible, enhancing the serene atmosphere by the water.

Home in Ozona

Luxe Private Waterfront Getaway with Pool in Ozona

A heated saltwater pool and spa are presented, set against a serene waterfront view. Lush palm trees and well-maintained landscaping frame the area, while the tranquil canal reflects the clear blue sky. Comfortable seating is positioned nearby for relaxation.

4.96 out of 5 average rating, 171 reviews

NEW Heated Salt Pool & Spa on Waterfront Canal

Superhost

4.82 out of 5 average rating, 104 reviews

Tampa | Heated Pool • Waterfront • Pet Friendly

Superhost

A spacious outdoor area features a shaped pool surrounded by a stone patio, complemented by lounge chairs. Tall palm trees provide natural shade, while a charming outdoor fireplace is visible in the background, enhancing the inviting atmosphere of the coastal location.

4.94 out of 5 average rating, 31 reviews

Mobbly bay full

4.98 out of 5 average rating, 52 reviews

A serene outdoor space is illuminated by string lights hanging from trees. A winding stone path leads to wooden steps ascending to a deck. Lush green grass surrounds a picnic table positioned on one side, enhancing the tranquil atmosphere of the lakefront setting.

Home in Palm Harbor

Waterfront Gem Near Clearwater • Swim Spa + Nature

Waterfront condo rentals

Condo in Clearwater Beach

A panoramic view captures the beach at sunset, showcasing soft white sand and tranquil turquoise waters. The sun sets gently on the horizon, casting warm colors across the sky and illuminating the landscape.

4.94 out of 5 average rating, 172 reviews

Beachfront Condo with Centerline Sunsets

Condo in Clearwater Beach

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

4.98 out of 5 average rating, 182 reviews

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Lounge chairs are arranged on the sandy beach, accompanied by thatched umbrellas providing shade. The calm waters of the bay are visible in the background, and a multi-story building is situated beyond the beach area.

4.86 out of 5 average rating, 142 reviews

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

A comfortable living area features a neutral-colored sofa, a round dining table, and a ceiling fan. Large sliding glass doors provide access to a balcony, allowing natural light to fill the space and offering views of palm trees outside.

4.93 out of 5 average rating, 251 reviews

Waterfront Condo - Sunset View of Tampa Bay

A serene balcony view captures a sunset over calm waters, with silhouetted palm trees in the distance. A small round table with a lantern sits next to a comfortable chair, creating an inviting space for relaxation.

4.95 out of 5 average rating, 386 reviews

Modern Waterfront Condo - Captivating Sunset Views

4.95 out of 5 average rating, 127 reviews

Tampa Bay Waterfront Views Rocky Point

4.99 out of 5 average rating, 243 reviews

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.

Condo in Madeira Beach

Rincón Divino MB 2 Balconies, Ocean & Marina Views