
Vacation rentals with a pool in Southport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southport
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Loft Apartment on Tree-Lined Street in Falmouth
Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Portland & Beach & Lighthouses! Romantic! Lovely
Location! You get the BEACH + Portland in minutes! HUGE BEDRM Romantic canopy bed w/ lux linens Chaise lounge couch turns into twin bed TV Giant mirror for weddings etc 35’ Great Rm w/ TV Kitchen *quality pots etc New Q Sofa Bed Priv entrance Beachy Light filled tall ceilings Spacious for 2-can fit 5 pond/bridge firepit 2 decks+patio Teak Furniture Open views New bthrm A/C Parking No stairs/Garden Level All in Cape: Crescent Beach 2 Lights State Pk Portland Headlight Prtlnd 8 min! 210780

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular eateries and breweries. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Apt in Victorian Mansion w/ Hot Tub, Pool, Parking
Mixing contemporary styling with old-world charm, the Apartment in the nationally registered Chapman House offers a relaxing, private stay, only minutes to downtown! Whether you plan to soak in the shared hot tub, cool down in our pool or relax by the fire pit, our half-acre yard offers a tranquil space for all. The apartment has a chef's kitchen, dining, and living room with gas fireplace. NB., use of the living room bed may incur a charge. We have a L2 EV charging outlet. #allarewelcome

Luxe Eco Studio near Back Cove
2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

Ocean View Retreat with Pool / Hot Tub
Newly renovated, saltwater pool with ocean views overlooking the Rockport harbor, with a vast garden. Fireplace and heated floors. Three bedrooms and four baths. Gourmet Kitchen. 2,500 square feet, in the heart of Rockport Village, walk to the harbor and local restaurants through the winding private path and gardens. There is a huge deck, a landscaped garden, and outdoor furniture. Walk down to the harbor, restaurants, and a coffee shop right in front of the house. Fast internet. No TV.

Maine Hacienda w/hot tub & seasonal pool
Our renovated suite at the foot of Deering Highlands is a 10 minute drive to downtown Portland. A cozy, quiet, modern space with a maritime edge. A short walk to Woodford’s corner and Forest Ave - home to many restaurants & coffee shops. The space includes a seasonal pool and year-round hot tub. Ideal for singles, couples or couples with one or two small children. A maximum of three adults can be accommodated. The hot tub is available all year. The pool is open early June to late September.

There's No Place Like Home
Our home is filled with cozy spaces to relax and unwind. From the outside deck and pool to the quaint private bedrooms! This family friendly BnB provides a kitchen, dining room and two living areas for a vacation haven . This home has the feel of a true BnB, yet the entire space is dedicated to our guests. We are on site in our in-law quarters, so are close at hand for questions and help if needed. Our home is located in a convenient, quiet and safe neighborhood with off street parking.

Resort-like 2 bed/1 bath - seasonal pool/hot tub
Munjoy Hill is Portland's premiere neighborhood. Enjoy ocean views along the Promenade. Share our seasonal private pool/hot tub with us from May thru Oct (dates vary). We have a swing set, lounge chairs, grill, play cornhole, tennis (we supply racquets/balls) watch baseball, basketball or take a walk to the playground close by. A short walk to East End Beach and the waterfront trail lead you to the famous Old Port. This property is one of a kind in the city

Sunny West End Guest Suite w/Harbor Views and Pool
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

Poolside Suite-Gateway to Portland
Beat summer heat with a private inground secluded pool. 7 minutes from downtown Portland. Bus line to Old Port across street. Parking in my driveway Walk to Mackworth Island from suite.. Sandy small beaches for accessing water/sunbathing . Casco Bay surrounds neighborhood for walking/biking. Pastry, fresh brewed coffee provided. Kurig in suite. The suite accommodates 2 adults. No children please. Backyard and pool available to the 2 suite guests only

Large private area, close to Rockland
Quiet and private neighborhood. Perfect for family or group getaways. Kid friendly. One mile from public ocean access, (WesKeag River) Five miles from downtown Rockland, and just minutes from downtown Thomaston. Three beautiful beaches within five miles. It’s the perfect place to stay while exploring the coastline, enjoying the downtown shops and restaurants, hiking and exploring the nearby cultural attractions. Two night minimum.
Popular amenities for Southport rentals with a pool
House rentals with a pool

Coastal, 3 bedroom, 2 bath home with pool!

Upscale OOB Beach House | Seasonal Heated Pool

New Listing! Pool, Hot tub & Lakes! Mins to Sebago

Luxe Liberty: Getaway with Heated Indoor Pool!

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

House in the woods

Dog Friendly Midcoast Cape

Maritime Meadows - Charming Resort-Style Home!
Condo rentals with a pool

LUXURY OCEANFRONT CONDO Best Location on the beach

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Condo in Old Orchard Beach

RARE 3 bedroom at The Resort Goose Rocks Beach!

Samoset-Affordable Luxury

Ocean View Studio Beach Condo

Lovely 2 bedroom riverside condo with pool

Maine, Beach front Condo! Vacation hotspot!
Other vacation rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home

A mile from the ocean, brand new, clean and comfy.

Lake Beach House at Poland Spring Resort

Luxury Condo on Water's Edge in Boothbay Harbor

The Hurkle Durkle House

4 Bedroom Riverside Home with Large Historic Barn

Relax at this 3BR "Gem of a Stay"

Charming East Boothbay Cottage w/ Large Yard!
Quick stats about vacation rentals with a pool in Southport
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ1,138 before taxes and fees
Total number of reviews
40 reviews
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Plainview Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Portland Vacation rentals
- Salem Vacation rentals
- Newport Vacation rentals
- Island of Montreal Vacation rentals
- Apartment rentals Southport
- Cabin rentals Southport
- Waterfront rentals Southport
- Cottage rentals Southport
- Pet-friendly rentals Southport
- Rentals with outdoor seating Southport
- Beachfront rentals Southport
- Boutique hotel rentals Southport
- Family-friendly rentals Southport
- Rentals with a fireplace Southport
- Rentals with beach access Southport
- House rentals Southport
- Fitness-friendly rentals Southport
- Rentals with a hot tub Southport
- Hotel rentals Southport
- Rentals with breakfast Southport
- Rentals with a fire pit Southport
- Rentals with a patio Southport
- Rentals with a washer and dryer Southport
- Rentals with a kayak Southport
- Rentals with pools Maine
- Rentals with pools United States
- Sebago Lake
- Scarborough Beach
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- Dunegrass Golf Club
- East End Beach
- Pemaquid Point Lighthouse
- Belgrade Lakes Golf Club
- Funtown Splashtown USA
- Willard Beach
- Samoset Resort
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Ferry Beach
- Cliff House Beach
- Palace Playland
- Fox Ridge Golf Club
- Freddy Beach
- Hunnewell Beach
- Bear Island Beach
- Brunswick Golf Club
- Maine Maritime Museum