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56 Retreats Available

Showing 56 properties

Across from Pool | Sleeps 6 | Ocean Pointe 3212

Tavernier, FL

Roll out of bed and into the pool, it's right across the way! This ocean-view 2BR/2BA sleeps 6 with a king, plus a queen-and-twin bunk the kids will fight over. We even leave you a...

6 Guests 2 Bedroom 2 Bath
from $239 / night
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Aqua Vista | Ocean View 2BR | Ocean Pointe 3307

Tavernier, FL

Aqua Vista is an ocean-view 2BR/2BA that sleeps 6 with a queen pull-out sofa and a full kitchen. Morning coffee on the balcony comes with ocean views and a bird chorus from the man...

6 Guests 2 Bedroom 2 Bath
from $239 / night
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Atlantic Serenity | Ocean View | Ocean Pointe 2407

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Top floor, ocean views and a fireplace. Yes, a fireplace in the Keys, for tho...

5 Guests 2 Bedroom 2 Bath
from $249 / night
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Blue Haven | Nature View 2BR | Ocean Pointe 1315

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

4 Guests 2 Bedroom 2 Bath
from $249 / night
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Boho Chic | Steps to Pool | Ocean Pointe 3214

Tavernier, FL

Boho Chic is right across from the pool and the tennis and pickleball courts, so you'll never be far from the action! 2BR/2BA with a king and a queen, Smart TVs, a work desk, pool...

4 Guests 2 Bedroom 2 Bath
from $269 / night
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Captain's Quarters | Top Floor | Ocean Pointe 4405

Tavernier, FL

Captain's Quarters is a top-floor 2BR/2BA with ocean views from the living room, kitchen and balcony! King suite, a queen-and-twin bunk room, two en-suite baths and Smart TVs every...

5 Guests 2 Bedroom 2 Bath
from $279 / night
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Coastal Joy | Ocean View 2BR | Ocean Pointe 3412

Tavernier, FL

Coastal Joy is a 2BR/2BA with stunning ocean views and fresh new decor and bedding. King in the primary, a queen in the guest room and sea breezes on the balcony. Joy is literally...

5 Guests 2 Bedroom 2 Bath
from $249 / night
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Coral Penthouse | End Unit | Ocean Pointe 4216

Tavernier, FL

Coral Penthouse is a corner end unit in Building 4, the closest to the open ocean, with the biggest layout and the most natural light at Ocean Pointe! King, two twins, a pull-out s...

5 Guests 2 Bedroom 2 Bath
from $299 / night
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Elevated Retreat | Sunset Access + Boat Basin

Islamorada, FL

Elevated, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Set...

4 Guests 2 Bedroom 2 Bath
from $299 / night
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Flamingo Flats | Marina View | Ocean Pointe 5306

Tavernier, FL

Flamingo Flats has double balconies with unobstructed marina, beach and ocean views! King suite, two twins with their own bath, a recliner for serious lounging and fast Wi-Fi if wo...

4 Guests 2 Bedroom 2 Bath
from $209 / night
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Heavenly Hideaway | Ocean View | Ocean Pointe 3306

Tavernier, FL

Heavenly Hideaway is a remodeled 2BR/2BA with ocean views over the mangrove preserve. Grab your coffee, hit the balcony and listen to the birds do their morning gossip! Plenty of s...

5 Guests 2 Bedroom 2 Bath
from $239 / night
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Island Time | 2 King Suites | Ocean Pointe 1203

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

6 Guests 2 Bedroom 2 Bath
from $189 / night
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Baja Penthouse | Corner Unit | Ocean Pointe 1416

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

4 Guests 2 Bedroom 2 Bath
from $249 / night
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Key Largo Bayfront Pool, Sunroom & Stunning Views!

Key Largo, FL

Escape to Tranquility at Moon Bay B - 304, a stunning bayfront apartment in Key Largo, Florida! Enjoy breathtaking sea views from this two-bedroom haven with direct ocean access. R...

5 Guests 2 Bedroom 1 Bath
from $250 / night
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Splash House | Private Pool & Spa | Key Largo

Key Largo, FL

Your own private pool AND an oversized spa? Yes, please! This 3-bedroom Key Largo home sleeps 7 across two separate floors: a 2BR/1BA main home upstairs with a full kitchen and lau...

7 Guests 3 Bedroom 2 Bath
from $359 / night
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Keys Bohemian | Renovated 2BR | Ocean Pointe 1312

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

6 Guests 2 Bedroom 2 Bath
from $229 / night
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Lazy Daze | Double King Suite | Ocean Pointe 2310

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Two kings, zero rock-paper-scissors! Lazy Daze has a king in both bedrooms, r...

4 Guests 2 Bedroom 2 Bath
from $239 / night
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Luxury 3BR Key Largo Townhome | Ocean & Pool Views

Key Largo, FL

Enjoy sweeping Atlantic Ocean and resort-pool views from this spacious 3BR/3BA townhome at Mariner’s Club. Designed for up to six guests, it features two king bedrooms, a twin bedr...

6 Guests 3 Bedroom 3 Bath
from $350 / night
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Marina & Ocean View | End Unit | Ocean Pointe 4201

Tavernier, FL

Marina AND ocean views from one end unit, a rare combo at Ocean Pointe! This 916 sq. ft. 2BR/2BA has extra windows, extra light and extra privacy. Primary suite with a walk-in show...

5 Guests 2 Bedroom 2 Bath
from $249 / night
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Marina to Ocean View 2BR | Ocean Pointe 5308

Tavernier, FL

Building 5 is closest to the pool, marina and beach, and this condo has two balconies with sweeping ocean and marina views! Upgraded 2BR/2BA with a king suite, a frameless glass sh...

4 Guests 2 Bedroom 2 Bath
from $249 / night
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Ocean View 2BR | Sleeps 6 | Ocean Pointe 2307

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Caribbean vibes without the passport! This modern coastal 2BR/2BA has ocean v...

6 Guests 2 Bedroom 2 Bath
from $239 / night
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Nauti Hideaway | 2 Balconies | Ocean Pointe 2314

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Two balconies, water views and a king bed you can admire them from without ge...

5 Guests 2 Bedroom 2 Bath
from $239 / night
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Corner Penthouse | Ocean Views | Ocean Pointe 5416

Tavernier, FL

Corner Penthouse has wraparound ocean views and the most natural light in the building! 2BR/2BA with a king suite, a queen-and-twin bunk room and an osprey nest in direct view from...

6 Guests 2 Bedroom 2 Bath
from $289 / night
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Ocean View Delight | Sea Gulls 310 ~ Monthly Rental

Tavernier, FL

Best View in the Keys - You will feel right at home in this beautifully renovated condo with FULL OCEAN VIEW. This complex has a uniquely large beach front. Plenty of room for barb...

4 Guests 2 Bedroom 2 Bath
from $245 / night
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Ocean View Gem | 2 Balconies | Ocean Pointe 3406

Tavernier, FL

Ocean View Gem is a top-floor 2BR/2BA with two balconies, right across from the pool! King suite, a guest room with its own bath and a stocked kitchen for cozy get-togethers. Pool...

5 Guests 2 Bedroom 2 Bath
from $239 / night
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Marina & Ocean View 2BR | Ocean Pointe 5305

Tavernier, FL

Marina views, beach views AND Atlantic views from one balcony! This 2BR/2BA in Building 5 has a king suite with a walk-in shower, a queen guest room and an in-unit washer/dryer. Wa...

5 Guests 2 Bedroom 2 Bath
from $209 / night
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Ocean View Treehouse | 2 Kings | Ocean Pointe 3403

Tavernier, FL

Ocean View Treehouse sits high above the mangroves with ocean views from every angle! Two king beds, two spa-style walk-in showers with rainfall heads and a stocked kitchen. Nature...

4 Guests 2 Bedroom 2 Bath
from $269 / night
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Paradise Palms | 2 Balconies | Ocean Pointe 1206

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

6 Guests 2 Bedroom 2 Bath
from $199 / night
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Pennekamp Hideaway | Water View, Kayaks & Pool Table

Key Largo, FL

Escape to paradise at this charming Key Largo house! Boasting stunning water views and a prime location near John Pennekamp Coral Reef State Park, this two-story home offers the pe...

7 Guests 2 Bedroom 1 Bath
from $329 / night
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Port Largo Villas Escape 5A

Key Largo, FL

Experience modern luxury in the heart of Key Largo! This stunning condo features an expansive oversized balcony, perfect for outdoor entertaining or simply enjoying the beautiful v...

6 Guests 2 Bedroom 2 Bath
from $269 / night
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Reel Key Largo | Next to Pool | Ocean Pointe 5209

Tavernier, FL

Best location at Ocean Pointe: across from the pool and next to the beach and marina! This 2BR/2BA has two balconies with full ocean views, a king suite, two twins and an in-unit w...

4 Guests 2 Bedroom 2 Bath
from $209 / night
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Retro Reef House | 2 Balconies | Ocean Pointe 5406

Tavernier, FL

Warning: may cause excessive smiling! Retro Reef House has two balconies, big water views, a king suite, a queen-over-twin bunk room and a sleeper sofa. A mermaid with a martini an...

6 Guests 2 Bedroom 2 Bath
from $279 / night
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Saltair Loft | Top Floor View | Ocean Pointe 1411

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

5 Guests 2 Bedroom 2 Bath
from $259 / night
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Salty Mermaid | 2 Balconies | Ocean Pointe 4406

Tavernier, FL

Salty Mermaid is a renovated top-floor 2BR/2BA with two balconies and more natural light than most at Ocean Pointe! King suite, queen-and-twin bunk room, two en-suite baths and a 6...

5 Guests 2 Bedroom 2 Bath
from $279 / night
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Sea Glass & Sunshine | 2BR | Ocean Pointe 2207

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Trade your alarm clock for sunshine! Sea Glass & Sunshine is a bright and col...

5 Guests 2 Bedroom 2 Bath
from $229 / night
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Sea View & Sunrise | Top Floor | Ocean Pointe 2412

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Top-floor sunrise views and a kitchen with a pot filler over the stove (cooks...

4 Guests 2 Bedroom 2 Bath
from $249 / night
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Sky Blue Escape | Ocean View | Ocean Pointe 1314

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

5 Guests 2 Bedroom 2 Bath
from $209 / night
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Sleeps 8 | Sunset + Boat Basin | Islamorada

Islamorada, FL

Unique property in the heart of Islamorada, ideal for groups and families traveling together. Enjoy rare access to a private boat basin and fishing jetty just steps away—perfect fo...

8 Guests 4 Bedroom 4 Bath
from $598 / night
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Sol & Sea | King, Nature View | Ocean Pointe 1204

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

3 Guests 1 Bedroom 1 Bath
from $179 / night
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Starfish Seas | Ocean View | Ocean Pointe 1302

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

4 Guests 2 Bedroom 2 Bath
from $199 / night
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Sunrise Oasis | Top Floor | Ocean Pointe 2411

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Early birds, this one's for you! Sunrise Oasis is a top-floor 2BR/2BA facing...

5 Guests 2 Bedroom 2 Bath
from $269 / night
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Sunrise Penthouse | 1BR 2BA | Ocean Pointe 3316

Tavernier, FL

Sunrise Penthouse is a bright, 916 sq. ft. 3rd-floor 1-bedroom with two full baths (no bathroom line, ever!). Wake up to Atlantic views and let the natural light do its thing. Perf...

4 Guests 1 Bedroom 2 Bath
from $249 / night
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Sunrise Sanctuary | Top Floor | Ocean Pointe 2415

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Sunrise Sanctuary is a top-floor 2BR/2BA with ocean and nature views, a king,...

6 Guests 2 Bedroom 2 Bath
from $263 / night
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Sunset Access + Boat Basin | Walkable Islamorada

Islamorada, FL

Unique, thoughtfully updated retreat in the heart of Islamorada with rare access to a private boat basin and fishing jetty—perfect for sunset views and relaxing by the water. Walk...

4 Guests 2 Bedroom 2 Bath
from $299 / night
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Sunshine Paradise | End Unit | Ocean Pointe 4402

Tavernier, FL

Sunshine Paradise is one of a kind! Eclectic island decor you won't find anywhere else, plus a fantastic ocean view. King, two twins and a pull-out sofa, so the whole crew fits. Ou...

5 Guests 2 Bedroom 2 Bath
from $269 / night
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The Fishing Shack | 2BR/2BA | Ocean Pointe 2312

Tavernier, FL

⚠️ ELEVATOR OUT OF SERVICE APRIL 12 – MAY 27, 2027 FOR MODERNIZATION. STAIRS ONLY DURING THESE DATES. Fish stories get bigger here, and "just one more cast" is always allowed! The...

4 Guests 2 Bedroom 2 Bath
from $239 / night
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The Happy Reef | Ocean View | Ocean Pointe 4209

Tavernier, FL

The Happy Reef has unobstructed Atlantic views from the living room AND the primary bedroom, in the most sought-after waterfront building! King and queen suites, a sofa bed and a d...

5 Guests 2 Bedroom 2 Bath
from $229 / night
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Reel Keys Getaway | Ocean View | Ocean Pointe 3405

Tavernier, FL

Welcome to the fourth floor, where the views are better and the ocean breeze is free! This fishing-themed 2BR/2BA has a front-row seat to the Atlantic, so your biggest decision is...

5 Guests 2 Bedroom 2 Bath
from $269 / night
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Tiki Time | Top Floor King | Ocean Pointe 1413

Tavernier, FL

⚠️ CONCRETE REPAIR WORK (SPALLING) UNDERWAY ON BUILDING 1 STARTING OCTOBER 2026. END DATE NOT YET SET. EXPECT CONSTRUCTION NOISE AND WORK CREWS AROUND THE BUILDING DURING THIS TIME...

4 Guests 1 Bedroom 1 Bath
from $189 / night
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Tropical Escape | Sea Gulls 407 ~ Weekly Rental

Tavernier, FL

Located right on the Atlantic Ocean, in the heart of the Florida Keys on Plantation Key - the sport fishing and diving capital of the world. Islamorada is your local hot spot for f...

4 Guests 2 Bedroom 2 Bath
from $229 / night
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Whispering Palms | Sea Gulls 210 ~ Weekly Rental

Tavernier, FL

NEWLY UPDATED! A peaceful sweeping view of the Atlantic stretches the entire length of this oversized balcony. FULL OCEAN VIEW! So, if you would like to swim in the heated pool,...

4 Guests 2 Bedroom 2 Bath
from $279 / night
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Tropical Paradise | Boat Parking | Pet Friendly

Miami, FL

Your Ideal South Florida Getaway Awaits! Experience comfort and convenience in this beautifully renovated one-story home featuring 3 spacious bedrooms and 3 full bathrooms. Bring y...

7 Guests 3 Bedroom 3 Bath
from $299 / night
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2-Home Estate | Sport Court | 2 Hot Tubs & Saunas

Asheville, NORTH CAROLINA

Two homes on a private Asheville ridgetop: the Lodge (4BR/5BA) and the A-Frame (3BR/2BA), steps apart and sleeping up to 24. Each home has its own hot tub and cedar sauna. They sha...

24 Guests 7 Bedroom 7 Bath
from $1,500 / night
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Biltmore Forest Retreat! Sauna Hot tub Game Rm

Asheville, NORTH CAROLINA

Welcome to our Biltmore Forest hidden retreat! Nestled back in the trees, this home is the perfect blend of a North Carolina mountain getaway meets Asheville entertainment house! J...

18 Guests 6 Bedroom 5 Bath
from $800 / night
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Ridgetop A-Frame | Hot Tub, Sauna & Pickleball

Asheville, NORTH CAROLINA

The A-Frame (3BR/2BA) sits on a private Asheville ridgetop and sleeps 8. It has three king bedrooms, a stone fireplace, its own hot tub and cedar barrel sauna, deck dining with a g...

8 Guests 3 Bedroom 2 Bath
from $600 / night
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Ridgetop Lodge | Hot Tub, Sauna & Red Stag Lounge

Asheville, NORTH CAROLINA

The Lodge (4BR/5BA) sits on a private Asheville ridgetop and sleeps 18. It has its own hot tub and cedar sauna, a covered patio with a pool table and ping-pong, and the Red Stag Lo...

18 Guests 4 Bedroom 5 Bath
from $800 / night
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