Waterfront vacation rentals in Oldsmar
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Oldsmar
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oldsmar waterfront rentals
Waterfront apartment rentals
Apartment in Treasure Island
4.91 out of 5 average rating, 281 reviewsAttractive Beachfront Studio - Live Like a Local!
Apartment in Madeira Beach
4.85 out of 5 average rating, 341 reviewsB⎈AT HOUSE OASIS⚓Steps to the water⚓Walk to Beach!
Apartment in Gulfport
4.99 out of 5 average rating, 110 reviewsSpacious Casa Marina in Gulfport
Apartment in Tampa
4.81 out of 5 average rating, 427 reviews↱Riverfront Escape w/included kayaks near dwntwn↰
Apartment in Saint Petersburg
4.89 out of 5 average rating, 147 reviewsThe Oasis
Apartment in Tampa
4.87 out of 5 average rating, 200 reviewsVintage 1925 Davis Island-pet friendly near beach
Apartment in Clearwater
4.86 out of 5 average rating, 106 reviewsCoastal Waterview Condo 2 Blocks to Beach
Apartment in Clearwater
4.91 out of 5 average rating, 113 reviewsAnchors UP #1, WALK to Beach, 1 bed/1 bath apt.
Waterfront house rentals
Home in Gulfport
4.89 out of 5 average rating, 119 reviewsThe Brenda Ann/Pet Friendly/Walk to downtown!
Home in Crystal Beach
4.94 out of 5 average rating, 186 reviewsBeach Side Beauty-heated Pool
Home in Indian Rocks Beach
4.86 out of 5 average rating, 309 reviewsStunning views! Spot dolphins from the pool!
Home in Tampa
4.85 out of 5 average rating, 243 reviewsSeminole Heights River Home
Home in Oldsmar
4.86 out of 5 average rating, 69 reviewsPrivate In-Law Suite with Beautiful Bay View
Home in Oldsmar
4.99 out of 5 average rating, 75 reviewsFountain House On Timberbay Lake
Home in Oldsmar
4.93 out of 5 average rating, 29 reviewsAmazing Private Beach Home
Home in Palm Harbor
4.92 out of 5 average rating, 84 reviewsLakefront home near beaches w/ waterview, pets ok
Waterfront condo rentals
Condo in Tampa
4.94 out of 5 average rating, 355 reviewsStunning Suite w/ WtrFrt Bay & Sunset Views
Condo in Tampa
4.95 out of 5 average rating, 131 reviewsWaterfront condo with sunset views of Tampa Bay.
Condo in Tampa
4.97 out of 5 average rating, 178 reviewsPondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Condo in Tampa
4.92 out of 5 average rating, 106 reviewsWaterfront Condo - Sunset View of Tampa Bay
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR Beachfront! Gorgeous sunsets!
Condo in St. Petersburg
4.97 out of 5 average rating, 145 reviewsSea La Vie- Studio by the bay!
Condo in Tierra Verde
4.96 out of 5 average rating, 242 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Condo in Tampa
4.83 out of 5 average rating, 150 reviewsTropical Serenity-Water View, Heated Pool Tiki Bar
Quick stats about waterfront rentals in Oldsmar
Total rentals
20 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
$30 before taxes and fees
Destinations to explore
- Tampa Vacation rentals
- Anna Maria Island Vacation rentals
- Sarasota Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Naples Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Waterfront rentals United States
- Waterfront rentals Orlando
- Waterfront rentals Florida
- Waterfront rentals Florida
- Waterfront rentals Kissimmee
- Fitness-friendly rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Monthly Rentals Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with pools Oldsmar
- Rentals with a washer and dryer Oldsmar
- Rentals with outdoor seating Oldsmar
- Kid-friendly rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with a patio Oldsmar
- House rentals Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with beach access Oldsmar
- Waterfront rentals Pinellas County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom