Vacation rentals in Saint James City

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Top-rated vacation rentals in Saint James City

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Matlacha

4.88 out of 5 average rating, 133 reviews

Mojito Island Cottage

Update: In September 2022 we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our canal. New large kitchen and one block from art galleries, restaurants and bars.

May 31 – Jun. 7

$198 CAD per night

Guest favourite

Apartment in Saint James City

4.93 out of 5 average rating, 84 reviews

Island Castaway--Free Kayaks

This is the perfect place to sit back, relax and enjoy the view. You have the privacy of a one-bedroom apartment with small kitchen and bath. We are close to great restaurants and some of the best music on the island. Open water and excellent fishing are minutes away. Two kayaks are set up for fishing and are available for guests to use so bring your fishing rod. Pine Island has no beachs, but Ft Myers Beach is about an hour away or take a ferry ride from Bokeelia to Cayo Costa for the day.

Mar. 30 – Apr. 6

$187 CAD per night

Guest favourite

Home in Saint James City

4.94 out of 5 average rating, 53 reviews

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is a laid back Old Florida atmosphere where you can get away from it all. 4 beds, 2 full baths. Steps to your dock & canal. Sandy secluded Beaches are minutes away by boat! Island Hopping! Don't have a boat, no worries-water taxis & rentals are plentiful on the Island. 4 seat Golf cart available. Steps to our private community pool & jet tub! Bikes & Kayaks & Games included.Sit back & relax! It's time 🌴🐠

Oct. 23 – 30

$201 CAD per night

Guest favourite

Cottage in Bokeelia

4.99 out of 5 average rating, 109 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. The dock is shared, but there is plenty of room! Lots of history on this beautiful island, with fishing you’ll be amazed with! Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources!

Aug. 8 – 15

$335 CAD per night

Guest favourite

Cottage in Saint James City

5.0 out of 5 average rating, 25 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. Just under 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!

Nov. 5 – 12

$325 CAD per night

Guest favourite

Home in Bokeelia

4.91 out of 5 average rating, 54 reviews

Cozy Duplex in the Heart of the Island

Enjoy the beautiful Florida weather on our screened front porch furnished with a dinning table and chairs gives you the option of dinning outside while enjoying Florida weather. The duplex has a one bedroom with a queen bed and on-suite bathroom. The room next to it has a sofa bed with TV and internet. A full size kitchen with all the utensils needed to cook any meal are at your disposal. The neighborhood is quiet and you are walking distance from most amenities. Relax and enjoy the weather.

Jul. 24 – 31

$215 CAD per night

Guest favourite

Home in Saint James City

5.0 out of 5 average rating, 12 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 2025-2026 bookings. Book Today!

Nov. 2 – 9

$315 CAD per night

Superhost

Home in Saint James City

New place to stay

Panoramic Views & Heated Pool!

Entire 3/2 home ON the water! STUNNING views of the Sanibel Causeway to Carlos Bay! A short boat ride to Sanibel & Captiva! Recently remodeled with NEW EVERYTHING and decorated beautifully! Large open living/kitchen/dining area with lots of seating. It has sliding glass doors that open fully to enjoy an all encompassing indoor/outdoor entertaining space! Everything you need for your short or long-term stay! You'll get the best sleep on these comfy beds! Coffee? Keurig & Nespresso machine.

Dec. 1 – 8

$1,123 CAD per night

Guest favourite

Farm stay in Saint James City

5.0 out of 5 average rating, 45 reviews

Private entire cottage on unique horse farm

Relax and unwind at this private and unique cottage on a beautiful horse farm. Close to dining, shopping, a variety of boating, fishing, and other water activities. Visit the Matlacha Bridge to cast a line with other fishing enthusiasts, or take a leisurely bike ride to tour the island (bikes/helmets provided). Grab a water taxi and visit surrounding sister islands with beautiful, secluded beaches. Please see the host guidebook for places to eat, things to do, and best ways to get there.

Feb. 5 – 12

$286 CAD per night

Guest favourite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 315 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Sep. 6 – 13

$146 CAD per night

Guest favourite

Home in Matlacha

5.0 out of 5 average rating, 141 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

Jul. 30 – Aug. 6

$713 CAD per night

Guest favourite

Home in Matlacha

4.98 out of 5 average rating, 181 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayaks

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 & 2 person kayaks for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

Jun. 11 – 18

$282 CAD per night