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Sugarloaf Vacation Rentals

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Bedrooms

Bathrooms

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5 km
44 rentals in Sugarloaf.
Palms Resort at Sugarloaf Beach - Main House, vacation rental in Sugarloaf
Palms Resort at Sugarloaf Beach - Main House, vacation rental in Sugarloaf
Palms Resort at Sugarloaf Beach - Main House, vacation rental in Sugarloaf

Palms Resort at Sugarloaf Beach - Main House

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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BRAND NEW WATERFRONT 3/2, vacation rental in Sugarloaf
BRAND NEW WATERFRONT 3/2, vacation rental in Sugarloaf
BRAND NEW WATERFRONT 3/2, vacation rental in Sugarloaf

BRAND NEW WATERFRONT 3/2

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bungalows at Sugarloaf Beach - The Palm., vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - The Palm., vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - The Palm., vacation rental in Sugarloaf

Bungalows at Sugarloaf Beach - The Palm.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazing Waterfront Home with Fabulous Pool and Sunset Views, vacation rental in Sugarloaf
Amazing Waterfront Home with Fabulous Pool and Sunset Views, vacation rental in Sugarloaf
Amazing Waterfront Home with Fabulous Pool and Sunset Views, vacation rental in Sugarloaf

Amazing Waterfront Home with Fabulous Pool and Sunset Views

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets, vacation rental in Sugarloaf
Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets, vacation rental in Sugarloaf
Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets, vacation rental in Sugarloaf

Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis, vacation rental in Sugarloaf
Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis, vacation rental in Sugarloaf
Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis, vacation rental in Sugarloaf

Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 17
Match: Sleeps
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Cassie’s Paradise - Luxury Vacation Rental in the Florida Keys, vacation rental in Sugarloaf
Cassie’s Paradise - Luxury Vacation Rental in the Florida Keys, vacation rental in Sugarloaf
Cassie’s Paradise - Luxury Vacation Rental in the Florida Keys, vacation rental in Sugarloaf

Cassie’s Paradise - Luxury Vacation Rental in the Florida Keys

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe, vacation rental in Sugarloaf
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe, vacation rental in Sugarloaf
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe, vacation rental in Sugarloaf

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Bungalows at Sugarloaf Beach - The Lighthouse, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - The Lighthouse, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - The Lighthouse, vacation rental in Sugarloaf

Bungalows at Sugarloaf Beach - The Lighthouse

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The following properties within 32 kms of Sugarloaf match all your filters:
The Sunset Cottage of Pelico Palms, vacation rental in Sugarloaf
The Sunset Cottage of Pelico Palms, vacation rental in Sugarloaf
The Sunset Cottage of Pelico Palms, vacation rental in Sugarloaf

The Sunset Cottage of Pelico Palms

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage, vacation rental in Sugarloaf
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage, vacation rental in Sugarloaf
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage, vacation rental in Sugarloaf

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront, vacation rental in Sugarloaf
Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront, vacation rental in Sugarloaf
Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront, vacation rental in Sugarloaf

Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key, vacation rental in Sugarloaf
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key, vacation rental in Sugarloaf
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key, vacation rental in Sugarloaf

Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bungalows at Sugarloaf Beach - Mi Azucar, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - Mi Azucar, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - Mi Azucar, vacation rental in Sugarloaf

Bungalows at Sugarloaf Beach - Mi Azucar

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Palms Resort at Sugarloaf Beach - Guest House, vacation rental in Sugarloaf
Palms Resort at Sugarloaf Beach - Guest House, vacation rental in Sugarloaf
Palms Resort at Sugarloaf Beach - Guest House, vacation rental in Sugarloaf

Palms Resort at Sugarloaf Beach - Guest House

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bungalows at Sugarloaf Beach - The Hemingway, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - The Hemingway, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - The Hemingway, vacation rental in Sugarloaf

Bungalows at Sugarloaf Beach - The Hemingway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Summer Sunsets are waiting for you !!, vacation rental in Sugarloaf
Summer Sunsets are waiting for you !!, vacation rental in Sugarloaf
Summer Sunsets are waiting for you !!, vacation rental in Sugarloaf

Summer Sunsets are waiting for you !!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Blue Wahoo-Perfect Keys Getaway, vacation rental in Sugarloaf
Blue Wahoo-Perfect Keys Getaway, vacation rental in Sugarloaf
Blue Wahoo-Perfect Keys Getaway, vacation rental in Sugarloaf

Blue Wahoo-Perfect Keys Getaway

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf
**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf
**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…, vacation rental in Sugarloaf

**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming Canal Front 3-bedroom house in Sugarloaf Key, vacation rental in Sugarloaf
Charming Canal Front 3-bedroom house in Sugarloaf Key, vacation rental in Sugarloaf
Charming Canal Front 3-bedroom house in Sugarloaf Key, vacation rental in Sugarloaf

Charming Canal Front 3-bedroom house in Sugarloaf Key

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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17ft Action craft flats boat included, vacation rental in Sugarloaf
17ft Action craft flats boat included, vacation rental in Sugarloaf
17ft Action craft flats boat included, vacation rental in Sugarloaf

17ft Action craft flats boat included

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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**CASSIE’S PARADISE * SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE, vacation rental in Sugarloaf
**CASSIE’S PARADISE * SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE, vacation rental in Sugarloaf
**CASSIE’S PARADISE * SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE, vacation rental in Sugarloaf

**CASSIE’S PARADISE * SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool, vacation rental in Sugarloaf
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool, vacation rental in Sugarloaf
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool, vacation rental in Sugarloaf

Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Dulces Suenos / Waterfront luxury at a DISCOUNT!
Why rent a home on a canal?, vacation rental in Sugarloaf
Dulces Suenos / Waterfront luxury at a DISCOUNT!
Why rent a home on a canal?, vacation rental in Sugarloaf
Dulces Suenos / Waterfront luxury at a DISCOUNT!
Why rent a home on a canal?, vacation rental in Sugarloaf

Dulces Suenos / Waterfront luxury at a DISCOUNT! Why rent a home on a canal?

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PARADISE FOUND on Sugarloaf Key! Please call *******-8105 for the latest updates, vacation rental in Sugarloaf
PARADISE FOUND on Sugarloaf Key! Please call *******-8105 for the latest updates, vacation rental in Sugarloaf
PARADISE FOUND on Sugarloaf Key! Please call *******-8105 for the latest updates, vacation rental in Sugarloaf

PARADISE FOUND on Sugarloaf Key! Please call *******-8105 for the latest updates

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Family Friendly House In Paradise, vacation rental in Sugarloaf
Family Friendly House In Paradise, vacation rental in Sugarloaf
Family Friendly House In Paradise, vacation rental in Sugarloaf

Family Friendly House In Paradise

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water, vacation rental in Sugarloaf
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water, vacation rental in Sugarloaf
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water, vacation rental in Sugarloaf

Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful spacious 4/4 on pristine swim canal. 20 min to key west, vacation rental in Sugarloaf
Beautiful spacious 4/4 on pristine swim canal. 20 min to key west, vacation rental in Sugarloaf
Beautiful spacious 4/4 on pristine swim canal. 20 min to key west, vacation rental in Sugarloaf

Beautiful spacious 4/4 on pristine swim canal. 20 min to key west

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and, vacation rental in Sugarloaf
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and, vacation rental in Sugarloaf
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and, vacation rental in Sugarloaf

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private, vacation rental in Sugarloaf
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private, vacation rental in Sugarloaf
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private, vacation rental in Sugarloaf

Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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THE BLACK MARLIN - 3 BEDROOM / 2.5 BATHROOM WITH POOL & TIKI HUT, vacation rental in Sugarloaf
THE BLACK MARLIN - 3 BEDROOM / 2.5 BATHROOM WITH POOL & TIKI HUT, vacation rental in Sugarloaf
THE BLACK MARLIN - 3 BEDROOM / 2.5 BATHROOM WITH POOL & TIKI HUT, vacation rental in Sugarloaf

THE BLACK MARLIN - 3 BEDROOM / 2.5 BATHROOM WITH POOL & TIKI HUT

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Modular House on beautiful Sugarloaf Key. Fabulous boating on your doorstep, vacation rental in Sugarloaf
Modular House on beautiful Sugarloaf Key. Fabulous boating on your doorstep, vacation rental in Sugarloaf
Modular House on beautiful Sugarloaf Key. Fabulous boating on your doorstep, vacation rental in Sugarloaf

Modular House on beautiful Sugarloaf Key. Fabulous boating on your doorstep

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Sugarloaf
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Sugarloaf
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Sugarloaf

The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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South Point Sunset - Florida Keys waterfront, vacation rental in Sugarloaf
South Point Sunset - Florida Keys waterfront, vacation rental in Sugarloaf
South Point Sunset - Florida Keys waterfront, vacation rental in Sugarloaf

South Point Sunset - Florida Keys waterfront

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Front Luxury Vacation Rental Near Key West, vacation rental in Sugarloaf
Ocean Front Luxury Vacation Rental Near Key West, vacation rental in Sugarloaf
Ocean Front Luxury Vacation Rental Near Key West, vacation rental in Sugarloaf

Ocean Front Luxury Vacation Rental Near Key West

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Sugarloaf Key Home With Beach, Dock and Canal!, vacation rental in Sugarloaf
Sugarloaf Key Home With Beach, Dock and Canal!, vacation rental in Sugarloaf
Sugarloaf Key Home With Beach, Dock and Canal!, vacation rental in Sugarloaf

Sugarloaf Key Home With Beach, Dock and Canal!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Sugarloaf Key Home, vacation rental in Sugarloaf
Waterfront Sugarloaf Key Home, vacation rental in Sugarloaf
Waterfront Sugarloaf Key Home, vacation rental in Sugarloaf

Waterfront Sugarloaf Key Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sugarloaf Sunrise, vacation rental in Sugarloaf
Sugarloaf Sunrise, vacation rental in Sugarloaf
Sugarloaf Sunrise, vacation rental in Sugarloaf

Sugarloaf Sunrise

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Perfect Catch: Family Fun and Boater's Bliss in the Keys!, vacation rental in Sugarloaf
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!, vacation rental in Sugarloaf
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!, vacation rental in Sugarloaf

The Perfect Catch: Family Fun and Boater's Bliss in the Keys!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bungalows at Sugarloaf Beach - Hammock House, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - Hammock House, vacation rental in Sugarloaf
Bungalows at Sugarloaf Beach - Hammock House, vacation rental in Sugarloaf

Bungalows at Sugarloaf Beach - Hammock House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite, vacation rental in Sugarloaf
Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite, vacation rental in Sugarloaf
Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite, vacation rental in Sugarloaf

Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21), vacation rental in Sugarloaf
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21), vacation rental in Sugarloaf
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21), vacation rental in Sugarloaf

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, vacation rental in Sugarloaf
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, vacation rental in Sugarloaf
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, vacation rental in Sugarloaf

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor, vacation rental in Sugarloaf
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor, vacation rental in Sugarloaf
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor, vacation rental in Sugarloaf

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-44 of 44
Frequently Asked Questions about Sugarloaf