Vacation Rentals in Toll Gate Shores, FL: Compare 10+ Sites & Save

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180 Best Vacation Rentals in Toll Gate Shores (Starting from $154)

Tollgate Tides
Tollgate Tides
House
Islamorada, FL, USA
0.1k from Toll Gate Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels, Beach rentals

2 Bedrooms6 Guests
New to Booking
$154
Average price / night
Check Availability
NEW!  Waterfront, 3 Bedroom, 3 Bath.  Keys Living, Peaceful Retreat
NEW! Waterfront, 3 Bedroom, 3 Bath. Keys Living, Peaceful Retreat
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$425
Average price / night
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Paradise Beach
Paradise Beach
House
Islamorada, FL, USA
0.5k from Toll Gate Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Accessible hotels

3 Bedrooms7 Guests
New to Booking
$242
Average price / night
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Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

2 Bedrooms6 Guests
New to Booking
$214
Average price / night
Check Availability
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Apartment
Islamorada, FL, USA
1.0k from Toll Gate Shores center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom10 Guests
New to Booking
$880
Average price / night
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Water Front 3/3 Family and Boat Friendly Home, Great Views
Water Front 3/3 Family and Boat Friendly Home, Great Views
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$295
Average price / night
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Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Apartment
Islamorada, FL, USA
1.0k from Toll Gate Shores center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$582
Average price / night
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A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$571
Average price / night
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Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Apartment
Islamorada, FL, USA
1.1k from Toll Gate Shores center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom18 Guests
New to Booking
$1388
Average price / night
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Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms12 Guests
10.0

Exceptional

21 reviews

$668
Average price / night
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Antigua Place
Antigua Place
House
Islamorada, FL, USA
1.5k from Toll Gate Shores center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$369
Average price / night
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\"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!\"
\"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!\"
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms12 Guests
10.0

Exceptional

20 reviews

$407
Average price / night
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Sandglass 4
Sandglass 4
House
Islamorada, FL, USA
1.9k from Toll Gate Shores center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

5 Bedrooms12 Guests
New to Booking
$640
Average price / night
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\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
House
Islamorada, FL, 33036, United States
0.1k from Toll Gate Shores center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$495
Average price / night
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Waterfront Wonder
Waterfront Wonder
House
Islamorada, FL, USA
1.9k from Toll Gate Shores center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

6 Bedrooms12 Guests
New to Booking
$1007
Average price / night
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Gorgeous bayfront Snappy Turtle: Spacious 4BR home in Islamorada with open water views!
Gorgeous bayfront Snappy Turtle: Spacious 4BR home in Islamorada with open water views!
House
Islamorada, FL, 33036, United States
0.2k from Toll Gate Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$1457
Average price / night
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Beachfront Villa at Islamorada BY THE GLAMHOMES
Beachfront Villa at Islamorada BY THE GLAMHOMES
Villa
Islamorada, FL, USA
3.2k from Toll Gate Shores center

Internet, View, Private Beach, Oceanfront, Sports/Activities, Ocean View, Fireplace/Heating

4 Bedrooms6 Guests
1.0

Review score

1 reviews

$7615
Average price / night
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3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
House
Islamorada, FL, 33036, United States
0.2k from Toll Gate Shores center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

3 Bedrooms10 Guests
New to Booking
$384
Average price / night
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Matecumbe Resort
Matecumbe Resort
Apartment
Islamorada, FL, USA
4.0k from Toll Gate Shores center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay

32 Bedrooms26 Guests
8.4

Very Good

332 reviews

$214
Average price / night
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Off the beaten path in one of Islamorada’s hidden gem of a community!.
Off the beaten path in one of Islamorada’s hidden gem of a community!.
House
Islamorada, FL, 33036, United States
0.2k from Toll Gate Shores center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$204
Average price / night
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Beach Residence Private overwater dock Heated Pool Mahi Key
Beach Residence Private overwater dock Heated Pool Mahi Key
House
Islamorada, FL, USA
4.2k from Toll Gate Shores center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$1282
Average price / night
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Coastal Studio Getaway – Second Floor with Partial Water Views
Coastal Studio Getaway – Second Floor with Partial Water Views
Apartment
Islamorada, FL, 33036, United States
0.3k from Toll Gate Shores center

AC, Balcony, Elevator, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

1 Bedroom3 Guests
9.2

Superb

5 reviews

$348
Average price / night
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Second Floor Den Suite – Sleeps 6 with Stunning Marina Views
Second Floor Den Suite – Sleeps 6 with Stunning Marina Views
Apartment
Islamorada, FL, 33036, United States
0.3k from Toll Gate Shores center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom5 Guests
New to Booking
$439
Average price / night
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Tide & Seek: Oceanview Studio Escape in Islamorada
Tide & Seek: Oceanview Studio Escape in Islamorada
Apartment
Islamorada, FL, 33036, United States
0.3k from Toll Gate Shores center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom3 Guests
New to Booking
$337
Average price / night
Check Availability
Relax in Sunset Cottage, bayfront 4BR pool home retreat in picturesque Islamorada.
Relax in Sunset Cottage, bayfront 4BR pool home retreat in picturesque Islamorada.
House
Islamorada, FL, 33036, United States
0.3k from Toll Gate Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$1040
Average price / night
Check Availability
Canalfront home in Safety Harbour in Islamorada, with 4 bedrooms and a pool.
Canalfront home in Safety Harbour in Islamorada, with 4 bedrooms and a pool.
House
Islamorada, FL, 33036, United States
0.3k from Toll Gate Shores center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$580
Average price / night
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Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
House
Islamorada, FL, 33036, United States
0.4k from Toll Gate Shores center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$277
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Toll Gate Shores.

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Frequently Asked Questions

You can explore 180 verified vacation rentals in Toll Gate Shores. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Toll Gate Shores vary depending on the season, property size, and location. Rates typically start from around $154 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Toll Gate Shores include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Toll Gate Shores welcome pets. Currently, 35 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Toll Gate Shores often include amenities such as Internet, Balcony/Terrace, and Laundry. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.