Holiday rentals in St. James City

5 out of 5 average rating, 13 reviews

Two comfortable chairs are positioned across from a large window, offering a view of a serene waterway. A small round table sits between them, enhancing the cozy setting. The gentle sunlight reflects off the water, creating a relaxing atmosphere.

Home in Hamlet

Bring Boat- speakeasy- 3/3 w/dock-Walk2town

It’s all about the WOW! You won’t want to leave this chic unique 3/3 full bath house water. Hidden fun secret SPEAKEASY. Keep it to yourself & then share w/ the rest of the family when the time is right. Tie your boat to your own dock & walk to restaurants& shops. Fully equipped kitchen, washer & dryer WiFi, TVs, games. 1 SMALL dog allowed for additional fee. 2 bikes, board games, donkey kong arcade & Bbq. Small events allowed. For larger family’s and lg dogs a 2nd home is available next door.

A renovated home in a vibrant shade of green features a covered porch with outdoor seating. Palm trees provide a tropical ambiance, while a gravel area surrounds the property. Large windows allow natural light to enter, creating a welcoming entrance for guests.

4.98 out of 5 average rating, 56 reviews

Enjoy the Salt Life w/Gulf Access Dock＋Kayak＋Bike

The "Pinfish", Gulf Access Island Home w/ Boat Dock. Located in the BEST area of Saint James City! Only a few minutes to open water. Perfect for those who want a relaxing stay and boaters with easy & quick access to fishing, shelling, or beaching. A Floating Dock for the included Kayaks & Paddleboards. This Renovated upgraded 2/1, sleeps 5, has everything you need. Fish from the dock, say hi to the Manatees that visit, bike/walk to the amazing local restaurants. Experience true Old Florida.

A spacious bedroom features a large bed with a textured white coverlet and decorative pillows. Soft lighting is provided by two bedside lamps. A wicker bench sits at the foot of the bed, adorned with rolled towels. Natural light enters through a window framed by sheer curtains.

5 out of 5 average rating, 9 reviews

Quiet Island Get Away - Fishing, Relaxation & Fun

Bring the family! Plenty of space for boat, RV, motorcycle or jetskis! Fully renovated. Small beach around the corner. Fishing, marinas, launching close by. TARPON capital! Aquatic Preserves are excellent for kayaking and canoeing. Community pool $2 for seniors. (Not on property) Take ferry to beautiful beaches of Sanibel, Captiva and Cabbage Key. Quiet - no noise, no crowds and no traffic. "Country living". This is NOT the 24/7 night life of Miami. Thirty minute drive to Ft. Myers.

A serene waterfront scene showcases a vibrant sunset, illuminating the sky in shades of orange and pink. Reflections are seen on the calm water, with palm trees framing the view. A paddle board rests on the grass beside a small table and chairs, inviting relaxation.

5 out of 5 average rating, 13 reviews

Charming Waterfront Home on Main Canal

Welcome to our waterfront home with direct access to the gulf! Located in St.James City, Pine Island, this beautifully renovated home, offers a spacious open concept style with two bedroom (Bedroom 1: Queen Bed+Bedroom 2: Bunk Bed (Queen Bottom+Full Top) and two bathrooms. Den with a Queen Size pullout sofa. Sanibel and Captiva Beach are a short boat ride away, area features world class fishing. Marina located on same canal, home has boat lift and dock to tie up to. Paddle board + tandem kayak

5 out of 5 average rating, 20 reviews

Island Retreat

Welcome to paradise in Pine Island, Florida! This stunning 3 bedroom, 2 bathroom house is the ultimate vacation rental for those seeking a tranquil and waterfront experience. Relax with the whole family at this peaceful retreat. Visit our IG page at PineIsland_Retreat for photos, information and vacation ideas. Long Stay Discounts applied for stays of 7 nights or more. Discounts vary by stay. Longer Stay, Greater Discounts! Early Bird Discounts available for 2026-2027 bookings. Book Today!

5 out of 5 average rating, 18 reviews

Island Paradise Awaits You

Discover Emerald Palms, a one-of-a-kind tropical retreat on historic Pine Island. Surrounded by lush gardens, seashell walking paths, and a sparkling private pool, this hidden gem feels like your very own island within the island. This custom cedar stilt home is thoughtfully decorated to evoke the timeless spirit of Ernest Hemingway’s island hideaways, offering a cozy, nostalgic ambiance with all the conveniences you need for a relaxing stay. More than a vacation home — it’s an experience.

Cottage in Saint James City

5 out of 5 average rating, 61 reviews

Waterside Cottage

Enjoy our peaceful little island paradise nestled beneath sprawling oaks and scattered palms just minutes from St James City’s restaurants and bars. Nearly 1/2 acre is yours to enjoy. Watch the manatees and dolphins swimming in the canal while you grill your catch of the day, or your fresh pick of the day from St James Fish House just down the street! Inside enjoy a fresh new contemporary and stylish cottage with everything you will need to make your stay comfortable, enjoyable and fun!

Apartment in Saint James City

A private pool is positioned beside a canal, framed by a white railing. Comfortable lounge chairs are arranged on the patio, overlooking calm waters reflecting a soft sunrise. Lush greenery and neighboring homes create a peaceful backdrop.

4.95 out of 5 average rating, 43 reviews

Island Time Private Poolside Retreat !

Welcome to Island Time! Enjoy all that Pine Island has to offer from this comfy poolside, waterfront ground level apartment with private entrance and boat dock access. Enjoy lounging at the private pool or BBQing on the patio. 15 miles of bike/walking trails are accessible from the front door, and several waterfront tiki bars and restaurants are within walking distance. Captiva, Sanibel and Fort Myers Beach are a short boat ride away. Explore Cape Coral, Fort Myers and nearby state parks.

A coastal-style house with a light blue exterior is seen from the driveway. Two garage doors are positioned beneath a covered entrance with steps leading to the front door. Palm trees and landscaping softly frame the home, complementing the inviting surroundings.

5 out of 5 average rating, 13 reviews

Island Getaway

Bring the whole family to this great place with lots of room for fun. House directly on canal to ocean with manatee and dolphins right at the dock! Biking, walking trails, kayaking, bring your own boat or jet skis, access to ocean short trip from the back yard canal access. Sit and enjoy sunsets from dock nightly! Outside dining area and upstairs patio give you great views of all that nature has to offer! Bring your telescope to star gaze. Enjoy the ocean breeze and views from all rooms!

Superhost

A round outdoor table with four metal chairs is positioned on a concrete patio. Surrounding plants add greenery to the setting, creating a relaxed outdoor dining area. The ground features gravel and a few decorative stones, enhancing the natural ambiance.

5 out of 5 average rating, 3 reviews

Sun Fish Island Retreat

Relax and enjoy the sun and serenity of this tranquil getaway. Bring your boat and take advantage of the boat ramp and slips on the Henley canal. Enjoy the local restaurants and live music or use the complete kitchen and grill to make your own special meals. Spend the day exploring the local attractions, or bring your water toys and explore the local waterways and islands. Very close to Matlacha, Great Calusa Blueway, The Colusa Heritage Trail, Galt preserve, and so much more!

A spacious outdoor area is presented, featuring a sparkling pool surrounded by lounge chairs. Lush greenery is visible, along with a shaded seating area nearby. The sunlit sky creates a vibrant atmosphere, emphasizing the serene environment of the poolside space.

4.91 out of 5 average rating, 33 reviews

Waterfront Retreat, Sleeps 8, Resort Style Pool

🌴 In July a Lemonade – Your Perfect Island Escape in St. James City! Welcome to your perfect island escape in St. James City! This stylish waterfront home has everything you need for a relaxing and fun-filled stay. You’ll be just minutes from great local restaurants, local marinas, and right on the water for easy access to Pine Island Sound and beyond. Whether you’re boating, biking, or just lounging by the pool, this home is your ideal base for a laid-back Florida vacation.

Aerial view of a spacious waterfront home surrounded by lush greenery. The property features a heated pool with a spa and a tiki hut, offering an outdoor kitchen area. The home's modern architecture and large windows provide ample natural light, while the nearby dock ensures easy access to the water.

5 out of 5 average rating, 8 reviews

Casa Baybreeze - Luxury on Water

Escape to paradise in this spacious 3BR/2.5BA waterfront pool home in St. James City, FL! Features include a designer kitchen w/ gas range, coffee bar, luxe appliances, pool table, heated pool & spa w/ waterfall, tiki hut w/ outdoor kitchen, and gulf-access dockage—just 5 mins to open water! Enjoy world-class fishing, tropical vibes, and walkable island dining. The master suite boasts a private terrace, bath & walk-in closet. This is Pine Island living at its finest!

Popular amenities for St. James City holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in St. James City

An outdoor area features a sparkling pool alongside a relaxing jacuzzi, both enclosed within a screened lanai. Comfortable seating is arranged in a lounge area, and a set of wooden chairs is positioned near a small table, surrounded by lush greenery and natural light.

5 out of 5 average rating, 14 reviews

Salt Life Serenity

Island in Saint James City

The exterior of the property features a light-colored facade with a circular aqua-colored emblem displayed on the wall. A smooth concrete pathway leads to the entrance, with a landscaped gravel area visible beside it. Nearby, palm trees and boats are partially seen along the canal.

5 out of 5 average rating, 5 reviews

Gulf Access Home St James City

Flat in Saint James City

5 out of 5 average rating, 3 reviews

The Hideaway

5 out of 5 average rating, 6 reviews

Private Waterfront Retreat w/ Dock & Firepit

An open concept living area features a spacious couch with decorative pillows, two comfortable armchairs, and a wooden coffee table. A dining space with colorful artwork and a modern kitchen with bar seating are visible, all illuminated by natural light from large windows.

5 out of 5 average rating, 4 reviews

Crab Cove Inn

The outdoor space features a private pool surrounded by beige tile flooring and lounge chairs. A shaded seating area is positioned nearby, with views of the water and docks under a blue sky filled with clouds. The atmosphere is calm and inviting.

5 out of 5 average rating, 4 reviews

Captain’s Getaway | Boatlift + Private Pool