Luxury Waterfront Estate with Private Beach & Pickleball, Captiva Island FL
Picture an August sunrise where osprey circle overhead, a docked sport-fisher gleams in early light, and a chilled-in-summer pool waits just steps away. That level of escapism defines this Captiva Island legend—an $5,000-a-night luxury vacation rental carved into four gated waterfront acres on prestigious Roosevelt Channel. If “private peninsula meets boutique resort” sounds like your idea of high-end summer living, keep reading.
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Quick-View Stats
- 11 bedrooms | 12 bathrooms | Sleeps 30
- Exact August 2025 nightly rate: $5,000 (verified July 2025)
- Four-night minimum stay
- Private beachfront plus deep-water dock
- Heated-and-chilled resort pool & oversized spa
Head-Turning Amenities
- Lighted tennis & pickleball court alongside a half-court for impromptu hoops
- 600-bottle temperature-controlled wine room—perfect for sunset tastings
- Chef’s kitchen with dual Sub-Zero fridges and seating for 30 at indoor + alfresco tables
- Full guest cottage, butler’s quarters, and on-site concierge to arrange yacht charters
- Pool cooled in summer, heated in winter—loungers rest on a sun-shelf steps from the bar
- Complimentary fleet of kayaks and paddleboards for dawn mangrove tours
Why This Estate Deserves a Spot on Your Bucket List
Captiva is synonymous with barefoot luxury, and this property amplifies the vibe. The main house and guest wings frame a palm-lined courtyard, so every bedroom spills onto tropical verandas. Morning coffee happens at a dock bench where dolphins break the glassy channel; evenings climax with chef-crafted stone-crab feasts under market lights. In a market crowded with high-end summer rentals, the seamless blend of beach, boating, and sport amenities vaults this estate into the top tier of $5,000-a-night luxury vacation rentals.
Local Luxe: Things to Do Within 30 Minutes
| Experience | Why It’s Worth Doing |
|---|---|
| Private Yacht Shelling Cruise | A captain steers you to remote sandbars; a naturalist cleans your Sanibel shells while champagne chills on ice. |
| Seaplane Lunch to Boca Grande | Ten-minute flight over emerald Gulf waters ends with tarpon tacos at The Pink Elephant, then home before sunset. |
| Golf at The Sanctuary | Tee times are scarce; concierge slots you at Captiva’s only Audubon-certified championship course. |
| Full-Service Sport-Fishing Charter | Chase tarpon or snook, then hand off the catch to an estate chef for dock-to-table ceviche. |
| Tween Waters Spa Day Pass | Hot-stone massages, rooftop yoga, and infinity-edge tranquility pool overlooking Pine Island Sound. |
| Sunset Polo at Al-Malek Farm | VIP cabana seating, artisanal grazing boards, and the crack of mallets under gilded skies. |
Rates & Availability
From $5,000 per night — August 2025
Check availability ➜
How This Listing Was Vetted
- Guest Satisfaction – Consistent 4.9+ average across verified reviews focusing on concierge service and immaculate upkeep.
- Concierge Depth – In-house team arranges private chefs, yacht outings, paddleboard yoga, even helicopter arrivals from RSW.
- Standout Amenities – Private beach, resort-style pool, wine cellar, sport courts, and dock suitable for 60-ft yachts.
Final Thought
Captiva Island nails the art of secluded glamour, and this address embodies it—from a vineyard-worthy wine room to a pool that adjusts its temperature like magic. Which amenity seals the deal for you: the private pickleball court or the chilled-in-summer pool? Share your pick in the comments and start planning one of the most unforgettable $5,000-a-night luxury vacation rentals of August 2025.
Prices verified July 2025; may fluctuate.