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Sugarloaf Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
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

Rental Home
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

Rental Home
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.

Rental Home
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

Rental Home
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

Rental Home
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

Rental Home
7 bedrooms
7 bathrooms
Sleeps 17
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

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
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

Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles 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

Rental Home
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

Rental Home
3 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

Rental Home
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

Rental Home
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

Rental Home
3 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

Rental Home
3 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

Rental Home
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 !!

Rental Home
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

Rental Home
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…

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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)

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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!

Rental Home
5 bedrooms
4 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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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

Rental Home
2 bedrooms
2 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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84), vacation rental in Sugarloaf
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84), vacation rental in Sugarloaf
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84), vacation rental in Sugarloaf

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Pool, vacation rental in Sugarloaf
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Pool, vacation rental in Sugarloaf
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Pool, vacation rental in Sugarloaf

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

Rental Home
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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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

Rental Home
4 bedrooms
4 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

Rental Home
3 bedrooms
4 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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PARADISE on Sugarloaf Key! Special September and October Rates.*******-8105, vacation rental in Sugarloaf
PARADISE on Sugarloaf Key! Special September and October Rates.*******-8105, vacation rental in Sugarloaf
PARADISE on Sugarloaf Key! Special September and October Rates.*******-8105, vacation rental in Sugarloaf

PARADISE on Sugarloaf Key! Special September and October Rates.*******-8105

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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?

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Canal Front 3-bedroom house in Sugarloaf Key, vacation rental in Sugarloaf
Canal Front 3-bedroom house in Sugarloaf Key, vacation rental in Sugarloaf
Canal Front 3-bedroom house in Sugarloaf Key, vacation rental in Sugarloaf

Canal Front 3-bedroom house in Sugarloaf Key

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-44 of 44
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