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South Portland, Maine Boat Rentals

Page 1 of 124 listings

Scenic, History, and  Fishing Charters out of Casco Bay
Tours in South Portland · 6 guests

Scenic, History, and Fishing Charters out of Casco Bay

5.0
Snoozed - Active 03 May 2025
Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.
Sailing in Portland · 6 guests

Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.

New
$850/day
Cruise Casco Bay aboard the Mickey Finn Trawler!
Powerboats in Falmouth · 6 guests

Cruise Casco Bay aboard the Mickey Finn Trawler!

5.0
$135+/hour
19’ Classic ski boat - day cruiser 225hp
Powerboats in Maine · 8 guests

19’ Classic ski boat - day cruiser 225hp

5.0
$75/hour
24ft Sebago Lake Cruise with Southbay Pontoon!
Powerboats in Casco · 6 guests

24ft Sebago Lake Cruise with Southbay Pontoon!

5.0
Snoozed - Active 03 May 2025
Wells Harbor Fishing Charter on 25ft C-Hawk Pilot House
Fishing in Wells · 6 guests

Wells Harbor Fishing Charter on 25ft C-Hawk Pilot House

5.0
$75+/hour
2021 Starcraft 20' Pontoon Delivery
Powerboats in Maine · 10 guests

2021 Starcraft 20' Pontoon Delivery

5.0
$350+/day
Hatteras 50ft Motor Yacht for Cruise or Sightseeing in Boothbay Harbor, Maine
Events in Boothbay Harbor · 6 guests

Hatteras 50ft Motor Yacht for Cruise or Sightseeing in Boothbay Harbor, Maine

New
$350/hour
17ft Starcraft Bowrider on Moose Pond in Denmark, Maine
Powerboats in Denmark · 8 guests

17ft Starcraft Bowrider on Moose Pond in Denmark, Maine

5.0
$650/day
Discover the Damariscotta River where 80% of Maine oysters are farmed
Events in Damariscotta · 49 guests

Discover the Damariscotta River where 80% of Maine oysters are farmed

New
$475/hour
Discover the Damariscotta River with a local captain!
Powerboats in Damariscotta · 6 guests

Discover the Damariscotta River with a local captain!

New
$300/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
Mastercraft X-Star Wakeboard / Surf Boat on Merrymeeting Lake
Powerboats in New Durham · 10 guests

Mastercraft X-Star Wakeboard / Surf Boat on Merrymeeting Lake

New
$225+/hour
Bennington 22' Pontoon on Merrymeeting Lake, New Hampshire
Powerboats in New Durham · 8 guests

Bennington 22' Pontoon on Merrymeeting Lake, New Hampshire

5.0
$215+/hour
Enjoy beautiful Maine at Damariscotta Lake!
Powerboats in Nobleboro · 8 guests

Enjoy beautiful Maine at Damariscotta Lake!

New
$260+/day
Fishing - Cruising - Swimming- Tubing on Silver Lake OR Conway Lake
Powerboats in Conway · 10 guests

Fishing - Cruising - Swimming- Tubing on Silver Lake OR Conway Lake

5.0
$125/hour
21' Bass Boat Charter in Nobleboro, Maine
Fishing in Nobleboro · 2 guests

21' Bass Boat Charter in Nobleboro, Maine

New
$50+/hour
18ft Glastron bow rider with 210hp
Powerboats in Readfield · 8 guests

18ft Glastron bow rider with 210hp

New
$300/day
24ft Manitou Pontoon
Powerboats in Readfield · 10 guests

24ft Manitou Pontoon

5.0
$280+/day
Sweetwater Pontoon 20ft
Powerboats in Readfield · 10 guests

Sweetwater Pontoon 20ft

5.0
$280+/day
Sea Ray 185 sport 135hp
Powerboats in Readfield · 8 guests

Sea Ray 185 sport 135hp

5.0
$250+/day
Trophy 2352 walkaround cuddy
Powerboats in Readfield · 6 guests

Trophy 2352 walkaround cuddy

New
$450+/day
24ft Bass Boat Rental in Sidney, Maine
Powerboats in Sidney · 3 guests

24ft Bass Boat Rental in Sidney, Maine

New
$38+/hour

South Portland Reviews

  1. MM

    Monica

    Sailing Adventure Aboard 44' Hunter Sailboat

    I cannot rave more about how AMAZING our experience was with Geoff! 1000 stars! It was absolutely beautiful and he made sure we had the best view of the sunset. We booked with him for an engagement photoshoot and he was super professional, fun, and incredibly helpful throughout helping us get the perfect shots. I’d recommend booking with Geoff for any occasion. I will definitely book again! Thanks Geoff!

  2. GT

    George

    Sailing Adventure Aboard 44' Hunter Sailboat

    Geoff was awesome! His sailboat was very clean and he was very accommodating. My wife and I went out to watch the sunset in Portsmouth and the itinerary was perfect. Geoff was really pleasant and we’ll definitely book with him again.

  3. SP

    Swapnil

    Scenic, History, and Fishing Charters out of Casco Bay

    We had a great trip out with Anthony. The boat was comfortable, clean and itinerary was ideal for the time with the trip around the islands ending with a beautiful sunset. Saw some seals along the way. We also learned interesting historical and ecological tidbits about the surrounding islands. Thanks for everything!

  4. James

    James

    Scenic, History, and Fishing Charters out of Casco Bay

    Anthony and Alyssa were great! They told us about the history and stories behind places we saw and we’re really nice without being overbearing. They took us by the lighthouses, islands and even stopped at a bar restaurant for lunch/drinks. Would highly recommend them for any kind of boating or fishing day off Portland-wonderful people!

  5. JD

    Julia

    24ft Sebago Lake Cruise with Southbay Pontoon!

    Anthony was great! He was responsive and timely in our communications beforehand. He was knowledgeable about the lake and had suggestions on where to go but was open to spending the afternoon doing what we wanted. We had a wonderful afternoon and everyone agreed it was our favorite activity of the trip. Would highly recommend booking with Anthony and would absolutely do it again next time I’m back in the area!

  6. KK

    Kayleen

    2021 Starcraft 20' Pontoon Delivery

    Sean’s pontoon boat is wonderful and was perfect for our family. He supplied everything we needed for endless tubing and water fun on the lake. His delivery/pick up if his boat was seamless and made our first family trip to Maine fantastic. Thanks Sean!! -The Kennedy Family