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Vacation rentals in Fort Myers

Saint James City! Just gorgeous! This is at one tip of our Island :-)

Welcome to our Island Home! House backs up to canal from sandy driveway! Very spacious front yard. Parking is only right in front of garage (2-3 cars/trailers can fit here). Other front yard space can be used for fun family games!

New dock ladder just installed! Now very easy to get in and out of boats and kayaks

Our Pool!! This pool is always warm and fun to swim in or just kick back and relax!

2 kayaks are included free for you to use during your stay. Hope you enjoy yourself out on the water!

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

2 bedrooms·2 baths

Saint James City • Florida

4.88(102 reviews)

$696.88 USD total for 3 nights

Oct 26 – 29, 2026

Quiet one bedroom in Bokeelia

Quiet one bedroom in Bokeelia

Quiet one bedroom in Bokeelia

Quiet one bedroom in Bokeelia

Quiet one bedroom in Bokeelia

Quiet one bedroom in Bokeelia

1 bedroom·1 bath

Bokeelia • Florida

$2,100.00 USD total for 7 nights

Oct 20 – 27, 2026

PurpleCove

2 bedrooms·2 baths

Saint James City • Florida

$7,191.75 USD total for 90 nights

Oct 20, 2026 – Jan 18, 2027

Fort Meyers Beachfront Paradise

Fort Meyers Beachfront Paradise

Fort Meyers Beachfront Paradise

Fort Meyers Beachfront Paradise

Fort Meyers Beachfront Paradise

Fort Meyers Beachfront Paradise

2 bedrooms·2 baths

Fort Myers • Florida

$10,225.00 USD total for 30 nights

Oct 20 – Nov 19, 2026

Driveway to the property

Driveway to the property

Island Retreat Villa

3 bedrooms·3 baths

Saint James City • Florida

$1,159.86 USD total for 4 nights

Oct 20 – 24, 2026

One of five satellite pools throughout the community. Our condo is equidistantly located between three of the five satellite pools & the resort style pool.

Tiki bar! The grilled Bang Bang shrimp is our favorite

Punta-Paradise!

Punta-Paradise!

Punta-Paradise!

2 bedrooms·2 baths

Punta Gorda • Florida

$3,090.00 USD total for 30 nights

Oct 20 – Nov 19, 2026

Seaside oasis studio with with heated pool

Seaside oasis studio with with heated pool

Seaside oasis studio with with heated pool

Seaside oasis studio with with heated pool

Seaside oasis studio with with heated pool

Seaside oasis studio with with heated pool

1 bedroom·1 bath

Fort Myers Beach • Florida

5(53 reviews)

$762.08 USD total for 4 nights

Oct 20 – 24, 2026

Heated Pool Home steps to the beach

Heated Pool Home steps to the beach

Heated Pool Home steps to the beach

Heated Pool Home steps to the beach

Heated Pool Home steps to the beach

Heated Pool Home steps to the beach

1 bedroom·1 bath

Fort Myers Beach • Florida

5(49 reviews)

$909.98 USD total for 4 nights

Oct 20 – 24, 2026

Beach view Pool Home

Beach view Pool Home

Beach view Pool Home

Beach view Pool Home

Beach view Pool Home

Beach view Pool Home

1 bedroom·1 bath

Fort Myers Beach • Florida

5(13 reviews)

$730.52 USD total for 3 nights

Oct 20 – 23, 2026

Go to the beach from expansive heated pool home

Go to the beach from expansive heated pool home

Go to the beach from expansive heated pool home

Go to the beach from expansive heated pool home

Go to the beach from expansive heated pool home

Go to the beach from expansive heated pool home

5 bedrooms·5 baths

Fort Myers Beach • Florida

5(8 reviews)

$4,164.04 USD total for 4 nights

Oct 20 – 24, 2026

This 2br/2ba Elevated Home with Two Boat Lifts

Offstreet parking

Screened in Porch

This 2br/2ba Elevated Home with Two Boat Lifts

2 bedrooms·2 baths

Saint James City • Florida

5(10 reviews)

$949.05 USD total for 3 nights

Oct 20 – 23, 2026

Maria Maria Vacation Home | Heated Pool | Lake view

Maria Maria Vacation Home | Heated Pool | Lake view

Maria Maria Vacation Home | Heated Pool | Lake view

Maria Maria Vacation Home | Heated Pool | Lake view

Maria Maria Vacation Home | Heated Pool | Lake view

Maria Maria Vacation Home | Heated Pool | Lake view

3 bedrooms·2 baths

Lehigh Acres • Florida

$1,856.20 USD total for 6 nights

Oct 20 – 26, 2026

The Yellow Vacation Home | Heated Pool & Spa

The Yellow Vacation Home | Heated Pool & Spa

The Yellow Vacation Home | Heated Pool & Spa

The Yellow Vacation Home | Heated Pool & Spa

The Yellow Vacation Home | Heated Pool & Spa

The Yellow Vacation Home | Heated Pool & Spa

3 bedrooms·2 baths

Lehigh Acres • Florida

$1,856.20 USD total for 6 nights

Oct 20 – 26, 2026

Sunset Stream Condo

Sunset Stream Condo

Sunset Stream Condo

Sunset Stream Condo

Sunset Stream Condo

Sunset Stream Condo

2 bedrooms·2 baths

Bonita Springs • Florida

$18,374.47 USD $16,615.04 USD total for 30 nights

Oct 20 – Nov 19, 2026

Our wheeled sun loungers make it easy to find your perfect spot — soak up the sun or roll into the shade for a little cool-down comfort.

Casa Bonita Florida provides more privacy than most Florida vacation homes, thanks to the spacious distance between properties. Experience peace and tranquility in a serene, secluded setting.

Casa Bonita Florida

Casa Bonita Florida

Casa Bonita Florida

Casa Bonita Florida

3 bedrooms·2 baths

Bonita Springs • Florida

5(8 reviews)

$1,120.56 USD total for 3 nights

Oct 20 – 23, 2026

Bright, cozy living room with stylish decor and plenty of natural light

Bright modern living room with cozy seating and open kitchen pass-through

Cozy modern living room with stylish decor and open kitchen connection

Bright, stylish living room with TV and open flow to the kitchen

Bright, stylish living room with large windows and cozy seating

Skelatal Listing: Rebecca Drost - 3705 Toulouse Ct, Punta Gorda, Florida 33950

4 bedrooms·3 baths

Punta Gorda • Florida

$30,897.00 USD total for 3 nights

Oct 20 – 23, 2026

Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

4 bedrooms·3 baths

Punta Gorda • Florida

$26,107.41 USD total for 3 nights

Oct 20 – 23, 2026

Botanika Breeze

Botanika Breeze

Botanika Breeze

Botanika Breeze

Botanika Breeze

Botanika Breeze

2 bedrooms·2 baths

Bonita Springs • Florida

5(3 reviews)

$6,923.15 USD total for 30 nights

Oct 20 – Nov 19, 2026

Bonita Lake Home

Bonita Lake Home

Bonita Lake Home

Bonita Lake Home

Bonita Lake Home

Bonita Lake Home

3 bedrooms·2 baths

Bonita Springs • Florida

4.89(82 reviews)

$1,275.71 USD total for 3 nights

Oct 20 – 23, 2026

NEW! Modern & Cozy Villa Riverpearl, Private Pool,

Oversized, Heated Saltwater Pool

Master Bed Room, King Sized Bed

Master Bed Room, King Sized Bed

Master Bathroom with bathtub

NEW! Modern & Cozy Villa Riverpearl, Private Pool,

4 bedrooms·2½ baths

Bonita Springs • Florida

$1,960.17 USD total for 4 nights

Oct 20 – 24, 2026

Take a dip in the pool, soak in the hot tub, enjoy a meal on the patio, take a snooze on the outside couch. You may never want to leave the backyard!

Back Yard - Fire Pit

The poolside loungers are calling for you!

Save the luggage and trunk space! We have many of the supplies you will need for a day at the beach.

A giant game of outside Jenga is fun for the whole crew!

Oasis in the Palms - Pool, Hot Tub, Beach Gear!

3 bedrooms·2 baths

Bonita Springs • Florida

$940.16 USD total for 3 nights

Oct 21 – 24, 2026

Sally's Seaside Escape

Sally's Seaside Escape

Sally's Seaside Escape

Sally's Seaside Escape

Sally's Seaside Escape

Sally's Seaside Escape

1 bedroom·1 bath

Bonita Springs • Florida

4.96(23 reviews)

$560.67 USD total for 3 nights

Oct 25 – 28, 2026

Latitude Adjustment on North Captiva- Beachfront

Eastern view provides and amazing sunrise and shade in the hot afternoon. Check out the manatee visiting the dock!

Latitude Adjustment on North Captiva- Beachfront

Latitude Adjustment on North Captiva- Beachfront

There are 5 miles of beautiful beaches to walk on North Captiva, two-thirds of which border a 700-acre state land preserve.

Latitude Adjustment on North Captiva- Beachfront

4 bedrooms·4 baths

Captiva • Florida

5(72 reviews)

$4,235.43 USD total for 5 nights

Nov 1 – 6, 2026

Covered Patio + Fire Table

Margarita Machine

Endless Yard Games & Adirondack Chairs

Villa Bonita - Pool, Hot Tub, Fire Pit

3 bedrooms·2 baths

Bonita Springs • Florida

$1,216.77 USD total for 3 nights

Oct 25 – 28, 2026