Calusa Land Trust and Nature Preserve of Pine Island, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Calusa Land Trust and Nature Preserve of Pine Island, Florida on RentalSaver.com!

Calusa Land Trust and Nature Preserve of Pine Island Rentals

From $658 per night (USD)
VRBO
Treetop getaway on a secluded Island with gulf coast beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to paradise! Your North Captiva Island stay includes The Island Club access to clubhouse pools, pool bar, hot t ...
From $658 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Snook/Sheephead @ 2 Fish Inn Waterside Location
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
The Snook/Sheephead @ the 2 Fish Inn offers an exceptional retreat for those seeking to explore the abundant charms of P ...
From $200 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Cabana @ 2 Fish Inn Pool Side
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Are you searching for your slice of island paradise while on vacation? Look no further than the Cabana at the 2 Fish Inn ...
From $203 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Welcome to the Gecko House! 3/2 in St. James on Monroe Canal!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterfront Escape in St. James City, Canal Home with Boat Tie-Up Welcome to your perfect waterfront getaway in the hear ...
From $245 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Luxurious waterfront home, pool, boat dock, fillet station, private guest suite
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Coastal Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $543 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Spacious, dog friendly home with pool, on waterway within minutes to the Gulf
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Bowline Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $446 per night (USD)
Expedia
From $641 per night (USD)
VRBO
North Captiva House on the Runway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to "One Margarita" on North Captiva Island! This charming 3-bedroom, 3-bath beach house is perfect for families ...
From $641 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Best Kept Secret #SJC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Saint James City at this pleasant house. Family friendly spacious home, with 3 bedrooms and ...
From $312 per night (USD)
VRBO
From $443 per night (USD)
VRBO
Weekday Special Rates! Waterfront Oasis w/ Pool, & Dock- Sleeps 8!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Waterfront Retreat in St. James City, Florida – Sleeps 8 Escape to this beautifully finished vacation home in charming ...
From $443 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Beautiful home with access to private beach, pool and hot tub.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Consider this townhome your home away from home while you visit Bokeelia. With 3 cozy bedrooms including a king, queen, ...
From $260 per night (USD)
Expedia
From $250 per night (USD)
VRBO
The Monroe Lookout! 2/2 Pool Waterfront Home!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Waterfront Paradise in St. James City! Escape to your perfect island getaway at this stunning home nestled on the vibran ...
From $250 per night (USD)
VRBO
From $341 per night (USD)
Expedia
3-bedroom waterfront pool house in Manatee Bay. BYOB: Bring your own boat
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover the beauty of Saint James City from this modern, updated 3-bedroom house in the Manatee Bay subdivision. Inside ...
From $341 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Bocilla Island Club Unit C-13
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to the charming Bocilla Island Club and discover the ultimate island getaway. This beautifully decorated vacation ...
From $193 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Captains Harbor Island Hide Away
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is one of Pine Island's most stunning and modernized two-bed and two-bath condo is waiting for you to live your bes ...
From $173 per night (USD)
Expedia
Click For Pricing
VRBO
Saint James City Boaters Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A cozy cottage, newly renovated, nestled in on Dawson cannel off of Pine Island sound just 30 minutes by boat to Sanibel ...
Click For Pricing
VRBO
From $279 per night (USD)
Expedia
Dream Vacation Pool and Waterfront Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
With its prime waterfront location, luxurious pool, and beautifully appointed living spaces, this 2-bedroom, 2-bathroom ...
From $279 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Gulf Access Lake View Bokeelia Condo with Boat Slip.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Walking, biking, boating, local dining and friendly people on Pine Island! This 2-bedroom condo is perfect for your esca ...
From $132 per night (USD)
VRBO
$Lazy Dolphin Retreat\n\n$
From $128 per night (USD)
Expedia
Lazy Dolphin Retreat\n\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
WARNING ** This property may cause: calmness, relaxation, mindfulness and happiness! Relax at this unique and peaceful ...
From $128 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Charming 3/2 Cottage in Bokeelia!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming 3/2 Cottage in Bokeelia! This cozy off-water property features 3 bedrooms, 2 bathrooms and a spacious living ro ...
From $240 per night (USD)
VRBO
Click For Pricing
Expedia
Beachfront! 2 Houses - Sleeps up to 16!
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Summary: 🌊 Gulf Front! 🏠2 professionally decorated homes 🛋️Sleeps 16 comfortably 🛥️ Shared boat dock - ask about ava ...
Click For Pricing
Expedia
From $492 per night (USD)
VRBO
House in Florida - Gulf of Mexico - Pine Island
Bedrooms:
5
Bathrooms:
4
Sleeps:
6
<p>Located in Bokeelia, this 4-bedroom, 5-bathroom vacation home lets you experience it all. Fans of nature and the outd ...
From $492 per night (USD)
VRBO
From $122 per night (USD)
Expedia
1/1 Condo in St. James City! Boat Slip Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1/1 Condo in St. James City! This cozy one-bedroom, one-bath condo offers beautiful views of the Monroe Canal. ...
From $122 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Tranquility in St. James City! 2/2 Overlooking Mangroves!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover tranquility in this charming 2-bedroom, 2-bath home nestled among lush mangroves. Enjoy a fully stocked kitchen ...
From $231 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Emerald Palms Island Escape - 4 BR Tropical Oasis on Pine Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A spectacular variety of tropical plants, flowers & seashell paths surround this custom built 2 story cedar siding villa ...
From $525 per night (USD)
VRBO
From $401 per night (USD)
VRBO
Osprey Lake House
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This stunning lake front vacation rental in Southwest Florida features a heated pool, a built-in grill and outdoor kitch ...
From $401 per night (USD)
VRBO
$Charming Pet-Friendly Bungalow... \n2 bed/2 bath Near Jug Creek & Boat Ramp$
From $220 per night (USD)
VRBO
Charming Pet-Friendly Bungalow... \n2 bed/2 bath Near Jug Creek & Boat Ramp
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to tranquility on Pine Island! Unplug and unwind at this charming 2-bedroom, 2-bath vacation retreat in the hear ...
From $220 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Bocilla Island Club H-43
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled in the heart of serenity, the fantastic Island Condo of H43 at Boccilla Island Club beckons you with its unparal ...
From $177 per night (USD)
VRBO
From $271 per night (USD)
Expedia
3BR Waterfront townhome Matlacha with hot tub, boat dock WiFi, bikes and kayaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located in Matlacha, enjoy what this 3-bedroom 2 full bath townhome has to offer. With 1 queen bed, 1 king bed, and 1 tw ...
From $271 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Relax in Paradise: 2-Bedroom Island Retreat with private Pool & Golf Cart!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Captain's Quarters – A Tropical Paradise on North Captiva Island Welcome to Captain's Quarters, your private island ret ...
From $446 per night (USD)
VRBO
From $119 per night (USD)
VRBO
Crab Cove Inn. 3/2 Direct Gulf Access with 50 ft sea wall.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Escape to our 3-bedroom, 2-bathroom canal front home with a fully equipped kitchen. Enjoy dinner on the deck or in the d ...
From $119 per night (USD)
VRBO
From $1566 per night (USD)
VRBO
Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: 🌊 Gulf Front Paradise 🏊‍♂️ Heated Private Saltwater Pool 🌅 Hot Tub Bliss: Enjoy stunning sunsets from the s ...
From $1566 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Margaritaville! 3bd2ba house in Saint James City 2 mins to open water w13k lift.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to this charming house in picturesque Saint James City. Close to everything on a quiet and quaint culdesac. With ...
From $326 per night (USD)
Expedia
From $143 per night (USD)
VRBO
Cozy fishing cottage on canal in Matlacha - 2 bedrooms and large outdoor space
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a relaxing stay at this lovely 2-bedroom house in Matlacha, with boat lift. The house features 2 queen beds, 2 bat ...
From $143 per night (USD)
VRBO
From $995 per night (USD)
Expedia
WHITE PELICAN WATCH- Unobstructed views, on beach, heated pool, slip NEW LISTING
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Your Dream Unobstructed Beachfront Getaway! Experience the ultimate in island living with our stunning 4-be ...
From $995 per night (USD)
Expedia
From $256 per night (USD)
VRBO
WATERFRONT, POOL, BOAT LIFT, WALKING DISTANCE TO RESTAURANTS, 2 BED/2 BATH
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover the beauty of Matlacha from this lovely 2-bedroom house. With a king bed and a Day bed that converts to a king ...
From $256 per night (USD)
VRBO
From $232 per night (USD)
VRBO
2 Mi to Boat Ramp: Home in Bokeelia
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Pet Friendly w/ Fee | Private Outdoor Shower | 2 Mi to Jug Creek Marina Surrounded by scenic sites and waterfront attra ...
From $232 per night (USD)
VRBO
From $803 per night (USD)
VRBO
Wicked Dolphins: Private Pool, Tiki Bar & Golf Cart Included
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Wicked Dolphins, your perfect island getaway on North Captiva Island. This 3-bedroom, 2-bathroom beach view h ...
From $803 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Bokeelia Oasis! Heated Pool, Sleeps 12!
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Escape to this stunning tropical retreat in Bokeelia, where relaxation meets luxury! This beautifully designed home feat ...
From $258 per night (USD)
Expedia
From $734 per night (USD)
VRBO
Silverseas Cottage-Luxury 3-bedroom, Steps to the Beach, Pool, 2 Carts, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
SILVERSEAS COTTAGE, The Perfect Beach Vacation Mere Steps From the Beach! Experience the ultimate beach vacation! Our ex ...
From $734 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Charlie's of Bokeelia
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy sun-filled days and serene sunsets at this peaceful Bokeelia retreat on the canal. Relax by the saltwater pool wit ...
From $372 per night (USD)
VRBO
From $351 per night (USD)
VRBO
New! Hidden- Speakeasy-penny floor. 3bd 3bath Boat dock & Walk 2 town FABULOUS
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Its all about the WOW!! Your Matlacha adventure begins at this chic 3-bedroom 3 full bath house. This home has been rebu ...
From $351 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Shellabration - Ocean Views and Family Fun!
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Summary: 🏡 Spacious luxury home – ensuite baths in every bedroom 🌊 Breathtaking ocean & preserve views 🏖 Beach-ready! ...
From $758 per night (USD)
Expedia
From $1060 per night (USD)
VRBO
4-bedroom Screened in Pool House with Bar! Golf Carts, Roof Top, and Amenities!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Island Time Beach House – Your Ultimate Getaway on North Captiva Island! Welcome to Island Time Beach House, a newly re ...
From $1060 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Sandpiper Oasis St James
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
to spend with. Set in a prime location, it offers modern amenities and comfortable accommodations for a memorable vacati ...
From $244 per night (USD)
Expedia
From $841 per night (USD)
VRBO
Beautiful Island Beach Home, Private Pool, Steps from the Best Beach, Golf Cart
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Sunny By You Beach House has EVERYTHING you need for a perfect North Captiva Island getaway! Welcome to Paradise on Nort ...
From $841 per night (USD)
VRBO
From $415 per night (USD)
Expedia
3-bedroom house in charming Saint James City with AC, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming house in Saint James City is a serene retreat for guests seeking a pleasant getaway. With 3 cozy bedrooms ...
From $415 per night (USD)
Expedia
From $182 per night (USD)
VRBO
ISLAND TIME! DOCK! POOL! KAYAKS! BOAT To BEACH! PETS ALLOWED!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is laid back Old Florida wher ...
From $182 per night (USD)
VRBO
From $1106 per night (USD)
Expedia
“BEACHFRONT” LUXURY ISLAND HOME. PRIVATE SWIM SPA~DOCK FISHING~GolfCart STUNNING
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Paraíso – A Luxury Beachfront Escape with Private Dock & Resort-Style Amenities. Welcome to Paraíso, your exclusive lux ...
From $1106 per night (USD)
Expedia
From $415 per night (USD)
VRBO
The Boat House! Home with 2 Living Spaces in Bokeelia, Sleeps 11!
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Spacious Waterfront Retreat in Bokeelia – Perfect for Families & Groups! Discover your ideal island getaway at this bea ...
From $415 per night (USD)
VRBO
From $139 per night (USD)
VRBO
Waterfront Paradise - 2BR/2BA Home with Gulf Access in Pine Island, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to your slice of coastal heaven just minutes from Sanibel, Fort Myers & Captiva! This beautifully decorated 2-be ...
From $139 per night (USD)
VRBO
$\Waterfront Gulf-Access Getaway – Fully Remodeled 2BR/2BA Vacation Retreat!$
From $206 per night (USD)
VRBO
\"Waterfront Gulf-Access Getaway – Fully Remodeled 2BR/2BA Vacation Retreat!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a peaceful stay at this 2-bedroom house in Saint James City. The cozy bedrooms feature 2 queen beds, perfect for a ...
From $206 per night (USD)
VRBO
From $1211 per night (USD)
Expedia
TURTLE & PIPER SHORES–Double Your Pleasure–6 BR BEACHFRONT - POOL, 2 GOLF CARTS
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
TURTLE & PIPER SHORES – DOUBLE YOUR PLEASURE – BEACHFRONT 6 BEDROOMS SIDE BY SIDE DUPLEX WITH PRIVATE POOL/HOT TUB COMBO ...
From $1211 per night (USD)
Expedia
From $736 per night (USD)
VRBO
SANDPIPER INN - TRUE BEACHFRONT Luxury; Pool/Hot tub & Golf cart NEW LISTING
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
SANDPIPER INN – BEACHFRONT CONDO – POOL – GOLF CART Experience the ultimate beachfront getaway at this stunning beachfro ...
From $736 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Waterfront Bungalow in Matlacha
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover the perfect getaway at this charming one-bedroom, one-bathroom waterfront bungalow. Nestled along the serene sh ...
From $223 per night (USD)
Expedia
From $397 per night (USD)
VRBO
3634 Bayview Avenue (Paradise): 3 BR, 2.5 BA House in Saint James City, Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your dream vacation destination, located in the highly sought-after waterfront community of Bayview Acres in ...
From $397 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Charming 2BR/2BA Pet-Friendly Home with Pool in St. James City!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming 2BR/2BA Pet-Friendly Home with Pool in St. James City! Welcome to your perfect Florida getaway! This beautiful ...
From $204 per night (USD)
Expedia
From $162 per night (USD)
VRBO
St James City brand new 3-bedroom home with WiFi, AC and boat lift
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Unwind in Saint James City at this adorable mobile home. With 3 cozy bedrooms including 2 queen beds and 1 twin bed, gue ...
From $162 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious 6-bedroom house in charming Captiva with WiFi, AC
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Get ready to relax in this 6-bedroom house in Captiva. This fabulous property offers WiFi, heating, a washing machine, A ...
Click For Pricing
Expedia
From $950 per night (USD)
VRBO
Villas in the Air – Elevated Island Living!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: 🏊‍♂️ Heated pool on the main level—no stairs for easy access! 🛋️ Thoughtfully designed with elevated interio ...
From $950 per night (USD)
VRBO
From $355 per night (USD)
VRBO
Beach house with Lake View, Boat Slip, Golf Cart, Pickleball and Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
WELCOME Quiet, safe, peaceful, golf cart community with Beautiful powder white undiscovered sandy beaches, and cryst ...
From $355 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Charming 2-bedroom condo in a beautiful Bokeelia waterfront community!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the perfect blend of Florida’s timeless charm and modern peacefulness at our recently renovated Bokeelia waterf ...
From $198 per night (USD)
VRBO
From $175 per night (USD)
Expedia
Matlacha Tiny Village-Iguana
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Ti ...
From $175 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Matlacha Tiny Village - Flamingo
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Tiny ...
From $199 per night (USD)
VRBO
From $207 per night (USD)
Expedia
Matlacha Tiny Village - Dolphin
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Tiny ...
From $207 per night (USD)
Expedia
$\Charming 3-Bedroom House One Canal from Bay with Boat Lift in Saint James City$
From $292 per night (USD)
VRBO
\"Charming 3-Bedroom House One Canal from Bay with Boat Lift in Saint James City
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Your cozy getaway in Saint James City awaits at this charming 3-bedroom home. Complete with a washing machine, iron, hai ...
From $292 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Waterfront 2BR/2BA Getaway w/Pool In Sunny Saint James City, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your perfect island getaway in beautiful St. James City, located on the southern tip of Pine Island, Florida. ...
From $313 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Charming 2-bedroom waterfront townhome with WiFi, AC Hot Tub and dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Peaceful recently renovated home on Matlacha Island. This 2 bedroom 1 full bath home sits on a waterfront canal just a f ...
From $174 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Paradise Point in St James City
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Charming 2Bd2Ba house in Saint James City heated pool, dock and lift. 1/2 Acre! This marvelous house is a gem waiting to ...
From $289 per night (USD)
Expedia
From $622 per night (USD)
VRBO
Waterfront with Private Dock!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: 🛥️ Private dock for boating, fishing, or relaxing 🚣‍♂️ Kayak launch next door — kayaks included! 🌅 Stunning ...
From $622 per night (USD)
VRBO
From $818 per night (USD)
Expedia
Casa Blanca on the Gulf: Elegant Beachfront Oasis
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: 🏖️ Beachfront paradise, bordered by untouched nature on both sides— serene, and truly private 🖼️ Coastal-chic ...
From $818 per night (USD)
Expedia
From $1827 per night (USD)
VRBO
Private Island Oasis! Gulf Views + Pool & Carts
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: 🌴 Total privacy in a lush garden retreat 🌅 Front-row sunsets with unobstructed gulf views 🌿 Scenic trails th ...
From $1827 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Waterfront Paradise in Matlacha – 2BR/2.5BA | Adults Only
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to this stunning adult-only waterfront retreat in the heart of charming Matlacha. This beautifully appointed 2-be ...
From $339 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Steps to Canal: St James City Home w/ Dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Beach Gear Provided | Walkable Boating Community | Laid-Back Living Secure your slice of paradise on Pine Island at thi ...
From $240 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Outstanding 3 BR waterfront pool home in Matlacha Isles / kayaks/ fishing poles
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fully stocked and beautifully furnished 3 bedroom/ 2 bath waterfront home with heated pool, kayaks, and fishing poles. L ...
From $276 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Matlacha Tiny Village
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Matlacha Tiny Village – Waterfront Paradise in the Heart of Old Florida! Discover the charm of Matlacha Tiny ...
From $526 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Charming 2-bedroom house in pleasant Saint James City with AC, WiFi, Boat Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in one of the sweetest parts of Saint James City, this delightful house offers 2 cozy bedrooms - one with a king ...
From $669 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Tiki Hut Paradise 4-bedroom Bokeelia House in the Sky w/ Golfcart on Island Time
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in Bokeelia, walking distance from the Pineland marina, this 4-bedroom house offers a peaceful elevated retreat ...
From $172 per night (USD)
VRBO
From $184 per night (USD)
Expedia
The Golden Flamingo – 2B/1Ba – Pool & Boat Ramp in Flamingo Bay
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Golden Flamingo – Old Florida Charm with Modern Comforts Welcome to The Golden Flamingo, your peaceful escape in th ...
From $184 per night (USD)
Expedia
From $143 per night (USD)
VRBO
Island Treasure! Brand new on an olde Florida island in the Gulf.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**Welcome to Island Treasure.** Nestled on a dirt, jungly road, this brand-new 3 bedroom, 2 bath oasis is your gateway ...
From $143 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Beautiful 3/3 Island Retreat with Heated Pool, Dock & Private Boat Ramp.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to your perfect Pine Island getaway at this beautifully elevated 3-bedroom, 3-bath retreat, designed for relaxati ...
From $261 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Charming 2-bedroom condo with AC, WiFi in serene Bokeelia FL.With boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2-bedroom condo is perfect for your escape to Bokeelia. With a king bed and a twin bed, guests can relax in this wo ...
From $256 per night (USD)
VRBO
From $510 per night (USD)
Expedia
CAPTAIN JACKS -LOOK NO FURTHER - THIS IS TRUE LUXURY! 6 P GOLF CART; POOL; SLIP
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Immerse yourself in the coastal charm of North Captiva Island with this beautiful townhome. From the living area and gue ...
From $510 per night (USD)
Expedia
From $172 per night (USD)
VRBO
The Flamingo at Sandpiper 2 bed 2 bath waterfront location with dock and lift
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A stunning 2-bedroom, 2-bathroom coastal retreat where you can park your boat right behind your house! Enjoy the ultimat ...
From $172 per night (USD)
VRBO
From $202 per night (USD)
Expedia
Waterfront getaway direct Gulf access, open living area two bed and two baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Welcome to Your Perfect Waterfront Getaway in St. James City, Pine Island! Experience the ultimate coastal retreat at th ...
From $202 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Stilted Waterfront Escape with Dock, Lift, Fire Pit & Game Room
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This 2 level vacation rental on stilts is a perfect getaway. The upper level boasts two bedrooms (both with ensuite bath ...
From $327 per night (USD)
VRBO
From $228 per night (USD)
VRBO
Sunset Retreat on Matlacha. Charming 2/1 house on Matlacha Pass.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our cozy 2-bedroom, 1-bathroom waterfront retreat in the heart of Matlacha, Florida! Nestled on the serene wa ...
From $228 per night (USD)
VRBO
From $640 per night (USD)
VRBO
☀️ Osprey's Nest | Relaxing Coastal Pool Retreat | Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
☀️ Osprey's Nest | Relaxing Coastal Pool Retreat | Sleeps 6 Welcome to Osprey's Nest—a bright and breezy 3-bedroom, 2-b ...
From $640 per night (USD)
VRBO
From $856 per night (USD)
Expedia
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)
Expedia
From $5582 per night (USD)
VRBO
614 MANGROVE MANOR-Elevator, Private Pool and Spa, Boat Dock
Bedrooms:
5
Bathrooms:
6
Sleeps:
19
Welcome to Mangrove Manor, your ultimate beachfront getaway! This stunning 5,886 sqft, 5-bedroom, 5-bathroom house is di ...
From $5582 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Coastal Comfort in Bokeelia – Pet Friendly w/ Pool & Boat Ramp Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Coastal Comfort in Bokeelia – Pet Friendly w/ Pool & Boat Ramp Access! Escape to this charming island retreat in Bokeel ...
From $255 per night (USD)
Expedia
From $683 per night (USD)
VRBO
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)
VRBO
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)
VRBO
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)
VRBO
From $904 per night (USD)
Expedia
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)
Expedia
From $481 per night (USD)
VRBO
Good Day Sunshine Townhome in Safety Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*** The FABULOUS “GOOD DAY SUNSHINE” is a LUXURY ISLAND TOWNHOME located on North Captiva Island! A Remote Barrier Islan ...
From $481 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 $146 per night (USD)
VRBO
Tranquil 3-bedroom house with AC in Saint James City- parking for boat or RV
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spacious and peaceful home located on beautiful Pine Island. Home has ample parking for a boat and/or RV. RV electrical ...
From $146 per night (USD)
VRBO
From $161 per night (USD)
Expedia
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)
Expedia
From $263 per night (USD)
VRBO
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)
VRBO
From $217 per night (USD)
Expedia
Fisherman’s Paradise Cozy Waterfront Retreat Matlacha - Your Dream Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to Fisherman’s Paradise in Matlacha, Florida! Welcome to your dream retreat in the heart of Matlacha—perfect for ...
From $217 per night (USD)
Expedia

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