Calusa Land Trust and Nature Preserve of Pine Island Rentals
From $856 per night (USD)VRBO
Smugglers Hideaway - Private Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your private island retreat on North Captiva Island! This stunning 3-bedroom, 3-bathroom home offers the perf ...
From $856 per night (USD)VRBO
From $683 per night (USD)Expedia
Sunset Beach: Secluded Beachfront Property with Stunning Island Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sunset Beach, a secluded beachfront property on North Captiva Island, perfect for a relaxing getaway. This 3- ...
From $683 per night (USD)Expedia
From $616 per night (USD)VRBO
Gorgeously-appointed 4-bedroom beach home steps away from pristine beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Nestled among coconut palms and lush tropical landscaping, the Turtle's Nest is steps away from Upper Captiva's white sa ...
From $616 per night (USD)VRBO
From $292 per night (USD)Expedia
Waterfront Oasis with Boat Lift & Hot Tub in Bokeelia
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Bask in endless sun at our Jugg Creek canal-front home, a stone's throw from Charlotte Harbor and iconic islands like Ca ...
From $292 per night (USD)Expedia
From $904 per night (USD)VRBO
Private Saltwater Pool + Steps to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This 3BR, 3BA island retreat sleeps 8 and is less than a one-minute walk to the beach (we timed it—with flip-flops). Whi ...
From $904 per night (USD)VRBO
From $1198 per night (USD)VRBO
Mint Julep - Spacious Beachfront Home with Gulf Views & Outdoor Showers
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Mint Julep, your perfect beachfront retreat on the pristine shores of North Captiva Island. This spacious h ...
From $1198 per night (USD)VRBO
From $161 per night (USD)VRBO
Cozy RV in Serene Bokeelia with AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your cozy getaway awaits in Bokeelia at this adorable recreational vehicle. This charming retreat features 1 queen bed i ...
From $161 per night (USD)VRBO
From $263 per night (USD)Expedia
Island Getaway – Waterfront Home with Gulf Access & optional Boat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to paradise at Island Getaway, the perfect waterfront retreat in St. James City on beautiful Pine Island! This ch ...
From $263 per night (USD)Expedia
From $295 per night (USD)VRBO
Enchanting Retreat - Pine Island Paradise - Roelens
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Pine Island Paradise There is a 30 night minimum stay required A Tropical Haven Beckons! Step into the tranquil be ...
From $295 per night (USD)VRBO
From $196 per night (USD)Expedia
Relax at Pine Island, 2 bed 2.5 bath. 3 Bikes, 2 Kayaks, 2 heated pools new pier
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Relax @ the North end of Pine Island in Bokeelia at this 2 bed 2.5 bath at Bocilla Island Club. Also know as BIC. This ...
From $196 per night (USD)Expedia
From $364 per night (USD)VRBO
Charming home near the ocean with gas grill, AC & Wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Salty Salutations Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $364 per night (USD)VRBO
From $289 per night (USD)Expedia
Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tropical Getaway in St. James City – 3BR/2BA w/ Boat Ramp Access Nearby! Welcome to your perfect island escape! Nestled ...
From $289 per night (USD)Expedia
From $458 per night (USD)VRBO
Luxe Pine Island Living: Historic Old Florida Gem!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Restored 1914 Home | Scenic Gulf Sunsets | Boat Slip Access Experience Old Florida elegance in this stunning Bokeelia v ...
From $458 per night (USD)VRBO
From $1649 per night (USD)Expedia
Gran Palacio-Beachfroont,Pool, Fishing & 360 Views, North Captiva Luxury Escape
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Gran Palacio is one of North Captiva’s flagship beachfront estates—luxurious, exclusive, and designed for unforgettable ...
From $1649 per night (USD)Expedia
From $434 per night (USD)VRBO
Water Views & Dock: Tranquil Matlacha Island Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dog Friendly w/ Fee | Recently Renovated (2025) | 2 Kayaks Ready for a laid-back island escape? Book an extended stay a ...
From $434 per night (USD)VRBO
From $293 per night (USD)VRBO
Waterfront Paradise in Matlacha
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to picturesque historic Matlacha. This charming newly renovated studio retreat offers a soothing ambiance perfect ...
From $293 per night (USD)VRBO
From $246 per night (USD)VRBO
Serene retreat with heated pool, family and dog friendly, close to Gulf, WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fishing in Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $246 per night (USD)VRBO
From $577 per night (USD)Expedia
Luxury Waterfront Retreat – 3BR/3BA | Sleeps 8 | Private Dock & Gulf Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
At Shell Pass Coastal Estate, escape to a world-class coastal sanctuary where luxury meets leisure in this exquisite 3-b ...
From $577 per night (USD)Expedia
From $176 per night (USD)VRBO
Fishermen's, Golfer's, Boater's, Kayaker's, Birder's & Snowbird's Dream!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, spacious, newly renovated home located right on Pine Island's only golf course and just minutes away from som ...
From $176 per night (USD)VRBO
From $214 per night (USD)Expedia
Turn Key Island Getaway. Pine Island. 3/2. Dock-BoatLift.\nFish,Golf,Boating
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Experience Saint James City like a local in this 3-bedroom , 2 full bath house. The bedrooms feature 1 king bed in the M ...
From $214 per night (USD)Expedia
From $563 per night (USD)VRBO
Luxury Waterfront Paradise in Bokeelia - Infinity Pool, Dock and Outdoor Bar
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to island living in this Seagull Bay 3-bedroom, 2-bath waterfront pool home on beautiful Bokeelia Island, locate ...
From $563 per night (USD)VRBO
From $265 per night (USD)Expedia
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Unwind in Bokeelia at this lovely house. This amazing property features 3 cozy bedrooms - 1 king bed and 2 queen beds, p ...
From $265 per night (USD)Expedia