Montgomery Cottages - Vacation Rentals in Island Walk

Quiet and comfortable From US $145
         

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10.0 (4 Reviews)
Apartment
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Hampton Inn - Naples - I-75 From US $99
         

9.0 (1007 Reviews)
Hotel
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Immokalee road close to everything From US $130
         

10.0 (5 Reviews)
Condo
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Private Suite on 3 Acres in North Naples! From US $217
         

10.0 (87 Reviews)
Apartment
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2 Villas, Pickleball,Heated pool, Naples escape. From US $1,336
         

10.0 (23 Reviews)
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The Secret Garden From US $148
         

10.0 (14 Reviews)
Apartment
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Luxury Places to Stay in Island Walk

Over 399+ Luxury Places to Stay in or Near Island Walk
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Private Golf Course Condo, Club Membership Available! From US $3,000
         

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8.7 (3 Reviews)
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Spacious Golf Club Condo, Membership Available! From US $2,550
         

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8.0 (1 Review)
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Naples Retreat – Pool, Pickleball & Cabana Oasis From US $1,275
         

10.0 (2 Reviews)
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Naples Retreat From US $1,084
         

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Top-Rated Vacation Rentals with a Pool in Island Walk

Over 259+ Top-Rated Vacation Rentals with a Pool in or Near Island Walk
Naples Beach , Golf and Country Club Naples Florida From US $143
         

10.0 (14 Reviews)
Condo
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Pet-Friendly Vacation Rentals in Island Walk

Over 92+ Pet-Friendly Vacation Rentals in or Near Island Walk
Orchid Estates From US $890
         

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Charming studio in tranquil Naples with AC. From US $122
         

10.0 (6 Reviews)
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Orchid Estates From US $575
         

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Comfortable and Convenient condo with Laundry & a pool From US $237
         

10.0 (2 Reviews)
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Model Home in gated community available for rent From US $313
         

10.0 (1 Review)
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Exquisite Home in Exclusive Community From US $612
         

9.6 (28 Reviews)
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Cozy new construction townhome. From US $150
         

9.6 (5 Reviews)
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Lovely Private Cottage, less than 5 miles to the beach! From US $180
         

9.4 (15 Reviews)
Cottage
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Large Vacation Homes & Villas in Island Walk

Over 43+ Large Vacation Homes & Villas in or Near Island Walk
7 Mi to Great Wolf Lodge Water Park: Luxury House From US $472
         

9.6 (38 Reviews)
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Cozy w/IMAX Theater,Heated Pool,Spa! Close to Paradise Sports Complex From US $801
         

Wheelchair Accessible Vacation Homes in Island Walk

Over 40+ Wheelchair Accessible Vacation Homes in or Near Island Walk
TownePlace Suites by Marriott Naples From US $170
         

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8.9 (501 Reviews)
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TownePlace Suites by Marriott Naples From US $129
         

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9.2 (914 Reviews)
Hotel
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2 BR 2 Bath Newly Renovated Condo From US $427
         

9.6 (5 Reviews)
Condo
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Island Walk Vacation Rentals and Airbnb Places to Stay Under $200

Over 122+ Island Walk Vacation Rentals and Airbnb Places to Stay Under $200
Roomy Recently Renovated Apt. From US $114
         

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8.8 (4 Reviews)
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Cozy 2-bedroom condo with AC in fabulous Naples From US $177
         

10.0 (1 Review)
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Charming Guest Quarters in Separate Building From US $146
         

9.8 (26 Reviews)
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Beautiful first floor condo with lake view! From US $116
         

9.8 (16 Reviews)
Condo
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Cypress Woods for Seasonal or Summer Stays W Golf From US $131
         

Instantly Bookable Vacation Homes in Island Walk

Over 151+ Instantly Bookable Vacation Homes in or Near Island Walk
A real Hidden Gem in Naples, Florida, rarely available. From US $241
         

STUNNING POOL HOME WITH LAKE VIEWS From US $673
         

8.6 (4 Reviews)
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BEAUTIFUL 3BD 2.5BA TOWNHOME, POOL, GYM. From US $287
         

6.6 (4 Reviews)
House
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This beautiful home with short drive to the beach. From US $318
         

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About Island Walk Vacation Rentals

With more than 408 Island Walk vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Island Walk.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Island Walk, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Island Walk. Places to stay near Island Walk are 1115.62 ft² on average, with prices averaging US $388 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Island Walk with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Island Walk

Type Count
Vacation Homes 190
Holiday Apartments 50
Villas 21
Hotels 4
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Island Walk

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Island Walk.

Weather in Island Walk

View the weather forecast for Island Walk before booking your Island Walk Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Island Walk Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Island Walk?
How many vacation rentals are available in Island Walk?

Currently, the total number of properties listed in 2026 is over 408 in the Island Walk area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Island Walk.