St. James City Pine Island Vacation Rentals & Private Rental Homes.

Waterfront Getaway in the Heart of Cherry Estates

Welcome to your Pine Island getaway in the heart of Cherry Estates in St. James City. This charming 2-bedroom, 2-bathroom waterfront home offers the perfect setting for a relaxing Southwest Florida vacation.

Boaters will love the convenient waterfront location and plenty of space to tie up your boat right at the property. Spend your days exploring the beautiful surrounding waterways, fishing, cruising, or simply enjoying the peacefu.......

2 Bedroom Vacation Home in Saint James City
Sleeps 4
Pet Friendly

Immaculate waterfront condo with one of the best views around. Direct access to Matlacha Pass and some of the worlds best fishing. This unit features 2 master bedrooms on the top floor with the living quarters on the main floor featuring a 1/2 bath. Come and relax in a beautiful, comfortable townhouse apartment located in a private enclave surrounded by canals and private boat docks. This town home has an AMAZING view of Pine Island Creek and Matlacha Pass. Boat out into the waters around Cayo C.......

2 Bedroom Vacation Home in Saint James City
Sleeps 4

Waterfront Paradise in St. James City | Heated Pool, Dock, Gulf Access
2 Bed | 2 Bath | Sleeps 4 | Boat Lift | Bikes | Direct Gulf Access
Escape to your perfect Southwest Florida getaway in this beautifully maintained waterfront home in St. James City! Nestled on a quiet canal just minutes from open water, this 2-bedroom, 2-bathroom retreat offers the ultimate island lifestyle with everything you need for a relaxing, adventure-filled vacation.
Property Highlights:
-Direct Gulf Acces.......

2 Bedroom Vacation Home in Saint James City
Sleeps 4
Pet Friendly

Welcome to your fresh and airy waterfront escape in St. James City! This beautifully maintained 3-bedroom, 2-bath pool home offers the perfect blend of comfort, relaxation, and boating convenience.

Enjoy bright, coastal-inspired living spaces and unwind in the Florida room, complete with ice-cold A/C (and heat during cooler months) and a charming queen-size swinging bed for additional sleeping space — a guest favorite!

Step outside to your private heated pool overlooking the cana.......

3 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Beautiful, Bright & Airy Condo with Spectacular Views of Pine Island Creek. This beautiful 2 bedroom 2 and 1/2 bath condo is in one of Pine Island's finest condo communities. Enjoy spectacular views of Pine Island Creek and Matlacha Pass from your private screened lanai. On those extra warm summer days you can close the sliders on the porch and still enjoy the extended living space in the nice AC! Everything you need for the perfect vacation is in this beautifully updated condo. Awesome Applianc.......

2 Bedroom Condo in Saint James City
Sleeps 4

Welcome to peace, welcome to paradise, welcome to PORCHFISH! This beautiful 3 bedroom, 2 bath home on Pine Island in St. James City is your vacation dream destination. This corner lot home is sure to please with charming coastal decor and comfortable furnishings in a very private setting with WiFi and Smart TVs throughout. The large screened-in porch overlooks the intersecting canals and protected mangroves which are filled with aquatic and aviary wildlife. Sip coffee while watching the manatees.......

3 Bedroom Vacation Home in Saint James City
Sleeps 6
Pet Friendly

Zuzu's Fancy is a wonderful 3 bedroom, 3 bathroom home in a quiet St. James City neighborhood. This home is sure to please with its beautiful coastal décor and comfortable furnishings. Dolphins are often seen playing in the back canal while manatees swim in the front canal by the fire-pit. This home offers a screened in porch overlooking the canal and mangroves, with a large Tiki Hut and large outdoor area. Bring your boat! You'll find a great canal side dock complete with water and electric.......

3 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Escape to The Hook Oar House, your perfect waterfront retreat for fishing, kayaking, and boating in St. James City, Florida.

Our immaculate 2-bed/2-bath elevated home offers easy access to Pine Island Sound and plenty of fish to be caught and dolphins/manatees to see.

Relax on the spacious deck or in our clean and comfortable living space, complete with modern amenities. Our new lower-level apartment provides additional space and privacy. You are only a short drive from the best r.......

2 Bedroom Vacation Home in Saint James City
Sleeps 5
Pet Friendly

This cozy efficiency apartment attached to the "Hook Oar House" has everything you need for a comfortable and relaxing stay. Whether you're a solo traveler or part of a group, this unit is the perfect spot to recharge after a long day of fishing or exploring the beautiful Pine Island Sound.

Recently remodeled after Hurricane Ian, this unit boasts brand new appliances and full kitchen amenities, including a Keurig coffee machine and propane grill to use. Plus, with the option to rent the .......

1 Bedroom Apartment in Saint James City
Sleeps 2
Pet Friendly

There is nothing better than slipping away to your tropical paradise vacation home knowing that everything is in tip top shape. This is exactly what you will find in this newly built 3 bedroom, 2 bath pool home in St. James City. This home is outfitted with granite counter tops, tile throughout, a screened lanai with a heated pool, hot tub, and a boat dock. Minutes out to the Gulf! With three bedrooms there is plenty of room for the whole family. *Boat lift is unavailable at this property. Welc.......

3 Bedroom Vacation Home in Saint James City
Sleeps 8

Grandpa Rudy first came to Pine Island in 1954 and our family has been coming ever since! Grab a cup of coffee (tea or adult beverage) and take a seat around the fire pit, the walk-around deck, or anywhere on the property that the fruit and coconut trees grow to start your "island time".

The Key West style home is one of the only 4 bedroom, 4 bath homes for rent on the island. 2 master bedrooms and a 3rd bedroom with twin beds are on the main level. A separated 4th is bedroom is downst.......

4 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Cute, clean and comfy 2 bed, 2 full bath mobile home in Saint James City, Florida on a quiet canal with 8000 pound boatlift and only a 15 minute troll out to open water, and all the beautiful beaches of Sanibel and Captiva. Enjoy the fishing and relax on the screened-in porch overlooking the dock or take a nap in the air conditioning on the large couch or in one of the two recliners. Eat-in kitchen also overlooks the canal and is perfect for watching the sunsets.

Boat lift will accommod.......

2 Bedroom Mobile home in Saint James City
Sleeps 4

🌴Unique and tranquil getaway. No hurricane damage
🐠Heated pool on the water… make your families dream vacation!
🏖Private home tucked away in your own spot on this exclusive island.
🚣🏻‍♂️4+ bedrooms, massive kitchen and living area overlooking the waterway you can kayak or Boat or Ferry ride to private sand beaches, restaurants and the best fishing in Florida. 🌞
🦩 Second kitchen for cooking big meals or storing extra snacks and drinks by the pool. ***NEW P.......

5 Bedroom Vacation Home in Saint James City
Sleeps 14

Waterfront Fisherman’s Paradise with Private Dock, Kayaks & Golf Cart –
Escape to Old Florida charm on Pine Island’s serene St. James City waterfront! This cozy canal-front home puts you steps from the Gulf waters with direct deep-water access – no bridges, no locks, just open boating to world-class fishing grounds. Perfect for anglers, families, couples, or snowbirds seeking an authentic island getaway.


Prime Waterfront Location & Local Hotspots
- Direct Gulf access vi.......

3 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Come relax in our Pine Island dream home--a charming, open and colorful floor plan will remind you that you are on a Florida vacation at every turn. Watch a thunderous storm from the furnished lanai, or fish for snook, snapper, crab, and shark from our dock. If you are lucky, catch a glimpse of dolphin or shark circling our fish light at night. Enjoy a peaceful stroll or bike ride to several restaurants and bait stores a few blocks away. World class beaches can be found by a ten minute boat .......

3 Bedroom Vacation Home in Saint James City
Sleeps 7

Come and enjoy this amazing location! The house is cozy and inviting, with a nice view of the canal, easy access to the golf waters for an amazing day of fishing. Close to Bars with live music, boat ramps, kayak rentals and many other attractions.
The house 🏠 is ready for your enjoyment, you will find on it:
* 2 Kayaks
* 1 golf cart
* Jacuzzi Spa 8 x 14ft
* 8000-pound boat lift
* Fishing rods 🎣
* Smart TVs

If you have a baby, you are also welcome!
W.......

4 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Island Vibe – Gulf Access Oasis with Heated Saltwater Pool & Spa

Your dream Pine Island getaway awaits at this newly remodeled 3-bedroom, 2-bath coastal retreat with a heated saltwater pool, spa soaker, and direct Gulf access. Bright, colorful, and full of tropical charm, this home offers the perfect balance of relaxation and fun!

The Space:
-Step inside and feel the vacation vibes!
-This home has been completely renovated with a vibrant island-inspired design and all the c.......

4 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Leave the everyday behind and embrace island time at this stunning 3-bedroom, 2½-bath coastal retreat. From the moment you arrive, you’ll feel like you’ve stepped into your own private paradise. Sip your morning coffee from the private balcony while taking in sweeping ocean views, or spend sun-filled afternoons lounging beside the sparkling private pool. Here, every moment is an invitation to slow down, unwind, and enjoy the vacation you deserve.

Inside, the home blends modern comfor.......

4 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Our beautiful newly remodeled home away from home is located in St. James City, Florida. It was just remodeled from the last two hurricanes and is better than ever! The home is just minutes away from Sanibel Island and Fort Myers Beach by boat. The living area is very spacious with a leather sectional and recliner with a 65" tv. The kitchen has a large island for great entertaining or just hanging out.

Our home is two bedroom, three and a half bath, all master suites with your very ow.......

2 Bedroom Vacation Home in Saint James City
Sleeps 6
Pet Friendly

Renovated, Open Concept 2 Bed 2 Bath Gulf Access Home in the Heart of St. James City. Fisherman’s Dream Awaits!! Two Man Kayak, (2)Bike to Local Bars and Preserves. Take a Short Boat Ride to Sandy Beaches including, Sanibel, Captiva, Bokeelia, Fort Meyers, Cayo Costa and more!! You won’t be disappointed!! 10,000lb Boat lift available for addition cost, inquire through host. Grocery stores just minutes away. Boat rental available just up the street. Fishing guides on Island. Lanai is fully sc.......

2 Bedroom Vacation Home in Saint James City
Sleeps 6

This is a fisherman;s paradise with a boat lift, and you are only minutes from the waters of Pine Island Sound. This area is know for some of the best fishing for snook, redfish, trout, grouper, snapper pompano, cabia and more. Make your way to the north past Sanibel, Captiva and Cayo Costa to the waters around Boca Grande Pass, and find the largest tarpon population in the world. After all of that wears you out, why not just relax and fish the sandy flats and mangroves always just minut.......

2 Bedroom Vacation Home in Saint James City
Sleeps 6
Pet Friendly

Your gulf access waterfront paradise is waiting in quaint Saint James City. 3 Kayaks for your use to explore or fish. Most popular StJames restaurants & live music are only minutes away. Enjoy the beautiful FL day & sunsets from the dock. Feeling adventurous? Explore the 2 nature preserves close to the house or take a ferry to North Captiva island.

BOATLIFT OCCUPIED AND NOT AVAILABLE FOR USE - please ask if you intend to bring a boat. The marina approximately a mile away has a boat ra.......

3 Bedroom Vacation Home in Saint James City
Sleeps 6

The relaxed atmosphere at this beautiful home is perfect for vacationers who want to get away from everyday stress and who want to enjoy the untouched nature of Florida. It is located in St. James City on South Pine Island with a broad water way and quick access to the Gulf of Mexico.
This home has been completely updated. The house has 3 bedrooms with two full bathrooms with walk in showers. The open floor plan is awesome for a vacation with family or friends. Kitchen has new appliances (sta.......

3 Bedroom Vacation Home in Saint James City
Sleeps 6

Unique custom-built Key West style piling home with outdoor shower, plentiful parking underneath as well as long driveway, all newer appliances (including washer and dryer), and welcoming porch in front, and screened porch in back. Old Florida living at its best with natural landscape, peaceful surroundings, and within minutes to water for kayaking and fishing. Open floor plan with lots of natural light. Pine ceilings in the kitchen-living area and wood floors throughout. Main bedroom with que.......

3 Bedroom Vacation Home in Saint James City
Sleeps 7
Pet Friendly

Welcome to our amazing waterfront vacation home, where luxury and comfort await you. This newly renovated retreat features not one, but three Master Suites, ensuring that every guest enjoys the utmost privacy and relaxation.

Step inside and be captivated by the impeccable design and attention to detail. Every inch of this home showcases top-notch craftsmanship and high-end finishes. From the elegant oak floors to the exotic granite and quartz countertops, no expense has been spared in cre.......

3 Bedroom Vacation Home in Saint James City
Sleeps 6

Your next getaway awaits at the beautiful Harpoon Lane in St. James City, FL. Our inviting 2-bedroom, 2-bathroom home is located in a serene neighborhood. This charming home offers dock access and quick access to fantastic fishing destinations, making it a dream retreat for fishing enthusiasts and nature lovers.

Step inside and be greeted by the warm, cozy ambiance of this well-maintained home. The living area provides a comfortable space to relax and unwind after a day of adventures. Th.......

2 Bedroom Mobile home in Saint James City
Sleeps 6

Experience the comfort and convenience of our exceptional ground level vacation rental home. Nestled on the Monroe Canal, this property offers quick access to the serene waters of San Carlos Bay and the captivating Gulf of Mexico.

Conveniently located, you'll find a variety of local restaurants serving delectable fare, as well as marinas and boat launches nearby. Whether you're a seasoned boater or simply looking to explore the waterways, this location is perfect for water enthusiasts.

3 Bedroom Vacation Home in Saint James City
Sleeps 6

Discover the perfect Winter getaway in Saint James City, FL with our inviting 1-bedroom, 1-bathroom condo. Located in a fantastic location, this cozy retreat offers a comfortable stay and a range of amenities for your enjoyment.

Step inside and experience the warm and welcoming ambiance of this well-appointed condo. The living area provides a cozy space to relax and unwind, while the fully-equipped kitchen allows you to prepare your favorite meals during your stay. The dining area is idea.......

1 Bedroom Condo in Saint James City
Sleeps 2

Immaculate saltwater canal Gulf access with no bridges minutes from open water. It doesn't get any better than this. Look no further this home will surely make your stay extremely comfortable. Large enclosed 12 x 28 Lanai overlooking the water with A/C is extremely relaxing and quiet. Large concrete dock allows for gathering next to the water and enjoyment of nature. Dolphins and Manatees do go up and down the channel and are an extra treat when seen. Bedroom 1 has a King Size bed, Bedroom 2 has.......

2 Bedroom Mobile home in Saint James City
Sleeps 6

Our Deluxe King Suite is the epitome of comfort and sophistication, offering a private escape with distinct features. Enjoy a serene bedroom with a luxurious king bed, complemented by Simmons Beautyrest plush mattresses and chic new furniture.

Experience the convenience of a fully equipped kitchen, complete with a range, microwave, refrigerator, and dishwasher, catering to all your culinary needs. The suite seamlessly combines comfort and functionality, allowing you to indulge in a home-c.......

1 Bedroom Vacation Home in Saint James City
Sleeps 4
Pet Friendly

No hurricane damage. This property is 100% ready to occupy. Nestled in Saint James City, Pine Island, Florida, this house offers the perfect waterfront escape for those seeking a slice of paradise. With a heated pool and new boat hoist for up to a 24ft V Bottom boat. Situated on a deep water canal , easy access to superb fishing opportunities, pristine beaches, and exceptional boating experiences at your doorstep, this is the ultimate destination for those looking to unwind and connect with the .......

3 Bedroom Vacation Home in Saint James City
Sleeps 8

15% off 5 days, 20% off 7+ days, 30% 30 days Your gulf access waterfront paradise awaits! Modern home with beautiful canal views. Kick back on the dock and relax watching manatees and dolphin play. Soak in the stunning sunset views! Bring your own boat to be out to the Gulf of Mexico within minutes. No boat, no problem. You can rent one right down the road or take ferry to the beautiful Captiva Island. Close to restaurants, grocery stores, and activities.

Sunshine State of Mind is a cozy .......

4 Bedroom Vacation Home in Saint James City
Sleeps 8
Pet Friendly

Enjoy the Island Life in our sun filled vacation home located off Manatee Bay, just north of Saint James City on Pine Island. The home is in a quiet and friendly neighborhood located on wide canal with direct access to the Gulf of Mexico. The waters here provide some of the finest fishing in the world and are a haven for birdwatchers and nature lovers.
Pine Island Sound & the intercostal waterway are a quick boat ride as well as the famous beaches of Sanibel & Captiva Island, Cayo Costa and B.......

4 Bedroom Villa in Saint James City
Sleeps 8

Our Seaside Villa Destin is idyllically located on Pine Island, which is situated in front of Cape Coral. Especially for boat lovers the villa is the perfect vacation domicile.

The way to the Gulf of Mexico is really not far and you can explore many beautiful islands around Pine Island and Cape Coral by boat. The boat dock may be used with pleasure. If you are interested in renting a boat, please contact us.
On the fully air-conditioned living area you will find two bedrooms, two bathr.......

2 Bedroom Vacation Home in Saint James City
Sleeps 4

Looking for your own piece of island paradise? This beautifully decorated spacious 2 bedroom, 2 bathroom home in St. James City, sits on a salt water canal minutes away by boat from the Intercoastal Waterway, Sanibel, Captiva, Ft. Myers Beach, and some of the best fishing in all of SW Florida! The home comes with a 7,000# boat lift and fish cleaning station on the dock where you can see manatee and dolphins in the canal. It is also within minutes of 5 restaurants and 2 grocery stores!

.......

2 Bedroom Mobile home in Saint James City
Sleeps 6

Nestled in one of the sweetest parts of Saint James City, this delightful house offers 2 cozy bedrooms - one with a king bed, large flat panel TV and the other with a queen bed. The property also features 2 bathrooms with showers and an additional living room space with a comfy sofa bed. Guests can enjoy amenities like an iron, washing machine, AC, heating, and WiFi during their stay.
Boat dock and in water Slip with direct deep water access. As south as you get on Pine Island. Views are sun.......

2 Bedroom Vacation Home in Saint James City
Sleeps 6