Oceanfront Rentals in Sugarloaf Key, FL: Compare 10+ Sites & Save

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  3.  USA

  4.  Florida
  5.  Sugarloaf Key

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188 Best Oceanfront Rentals in Sugarloaf Key (Starting from $156)

Villa of the Setting Sun
Villa of the Setting Sun
House
Sugarloaf Key, Florida, USA
1.8k from Sugarloaf Key center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
Average price / night
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**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
House
Sugarloaf Key, FL, 33042, United States
1.2k from Sugarloaf Key center

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

4 Bedrooms8 Guests
New to Booking
$638
Average price / night
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Palms Resort Main House - Key West
Palms Resort Main House - Key West
House
Sugarloaf Shores, FL, USA
4.1k from Sugarloaf Key center

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

1 Bedroom12 Guests
New to Booking
$1248
Average price / night
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Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
House
SugarLoaf, FL, 33042, United States
1.3k from Sugarloaf Key center

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

5 Bedrooms12 Guests
9.6

Exceptional

8 reviews

$297
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
4.1k from Sugarloaf Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom8 Guests
New to Booking
$1198
Average price / night
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Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
1.8k from Sugarloaf Key center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
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Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
4.2k from Sugarloaf Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
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PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
House
Summerland Key, FL, 33042, United States
1.8k from Sugarloaf Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$384
Average price / night
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Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
4.3k from Sugarloaf Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
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Sunset Views • Heated Pool • Fire Pit • Sleeps 6
Sunset Views • Heated Pool • Fire Pit • Sleeps 6
House
Sugarloaf Key, FL, 33042, United States
2.0k from Sugarloaf Key center

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

2 Bedrooms6 Guests
New to Booking
$428
Average price / night
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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
4.5k from Sugarloaf Key center

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

3 Bedrooms7 Guests
New to Booking
$583
Average price / night
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 Canal Front 3-bedroom house in Sugarloaf Key
Canal Front 3-bedroom house in Sugarloaf Key
House
Summerland Key, FL, 33042, United States
2.1k from Sugarloaf Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$343
Average price / night
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Tranquility in Paradise - Cudjoe
Tranquility in Paradise - Cudjoe
House
Summerland Key, FL, USA
4.7k from Sugarloaf Key center

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

3 Bedrooms8 Guests
New to Booking
$156
Average price / night
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Villa and Bungalow of Pelico Palms
Villa and Bungalow of Pelico Palms
Villa
Monroe County, FL, 33042, United States
2.1k from Sugarloaf Key center

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

6 Bedrooms14 Guests
New to Booking
$1751
Average price / night
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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
5.1k from Sugarloaf Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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Private Pool Oasis — 3 King Suites | 30 Min to Key West
Private Pool Oasis — 3 King Suites | 30 Min to Key West
House
Monroe County, FL, 33042, United States
2.1k from Sugarloaf Key center

AC, Barbecue, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
7.6

Good

5 reviews

$945
Average price / night
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Parrotfish Pointe
Parrotfish Pointe
House
Cudjoe Key, FL, USA
6.8k from Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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Pelico Palms Estate.
Pelico Palms Estate.
House
Monroe County, FL, 33042, United States
2.1k from Sugarloaf Key center

AC, Arcade, Balcony, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

9 Bedrooms20 Guests
9.8

Exceptional

7 reviews

$3053
Average price / night
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Dolphin Daydreams by Last Key Realty
Dolphin Daydreams by Last Key Realty
House
Cudjoe Key, FL, USA
7.5k from Sugarloaf Key center

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

1 Bedroom4 Guests
New to Booking
$351
Average price / night
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Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning Views
House
Summerland Key, FL, 33042, United States
2.2k from Sugarloaf Key center

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

1 Bedroom4 Guests
New to Booking
$692
Average price / night
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Pelican's Roost, Waterfront comfort at Venture Out
Pelican's Roost, Waterfront comfort at Venture Out
House
Cudjoe Key, FL, USA
7.6k from Sugarloaf Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms5 Guests
9.2

Superb

15 reviews

$303
Average price / night
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Waterfront, Pet Friendly - Loggerhead Lagoon
Waterfront, Pet Friendly - Loggerhead Lagoon
House
Sugarloaf Key, FL, 33042, United States
2.9k from Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
New to Booking
$336
Average price / night
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Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
House
Upper Sugarloaf Key, FL, 33042, United States
3.3k from Sugarloaf Key center

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

4 Bedrooms12 Guests
9.2

Superb

7 reviews

$534
Average price / night
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Beach Getaway in the Florida Keys
Beach Getaway in the Florida Keys
House
SUGARLOAF KEY, FL, 33042, United States
4.1k from Sugarloaf Key center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms8 Guests
8.4

Very Good

7 reviews

$1225
Average price / night
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Florida Keys Beach Getaway
Florida Keys Beach Getaway
House
Sugarloaf Key, FL, 33042, United States
4.1k from Sugarloaf Key center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

5 Bedrooms12 Guests
9.8

Exceptional

28 reviews

$1818
Average price / night
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CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT
CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT
House
Cudjoe Key, FL, 33042, United States
4.2k from Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$486
Average price / night
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Private and Exclusive Beach Getaway
Private and Exclusive Beach Getaway
House
Sugarloaf Key, FL, 33042, United States
4.2k from Sugarloaf Key center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
8.0

Good

2 reviews

$1969
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 Oceanfront Rentals in Sugarloaf Key.

Stay Near Sugarloaf Key's Top Attractions

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Sugarloaf Key Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 188 verified oceanfront rentals in Sugarloaf Key. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Sugarloaf Key vary depending on the property size, exact beachfront location, and season. Rates typically start from around $156 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Sugarloaf Key offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Sugarloaf Key welcome pets. Currently, 33 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Sugarloaf Key often include features designed for a comfortable coastal stay, such as Ocean View, View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.