La Siesta Resort & Villas – Islamorada Resort Review
Last updated: August 28, 2026
Choose La Siesta Resort & Villas if...
- You're a family wanting oceanfront cottages with full kitchens, heated pool, and water taxi to sister resorts
- You're a couple wanting Tulum-inspired oceanfront rooms with poolside dining and sunsets
- You're a boater wanting transient marina slips with access to Three Waters' larger marina
Skip La Siesta Resort & Villas if...
- You want an on-site spa or fitness center — those are at sister resorts via water taxi
- You're watching costs — a $65/day resort fee adds significantly to rates
- You prefer paying cash — the resort collection is cashless
AskTheKeys Traveler Match
How well does La Siesta Resort & Villas fit your trip?
Before you book — the one trade-off
La Siesta leans on its sister resorts for spa and fitness, reached by water taxi — and the $65/day resort fee plus cashless policy add up.
AskTheKeys Decision SummaryLa Siesta Resort & Villas is best for families, couples, and boaters wanting an oceanfront resort with on-site dining, marina slips, heated zero-entry pool, complimentary water sports, and pet-friendly accommodations in Islamorada — with water taxi access to sister resorts Amara Cay and Three Waters. It is not ideal for guests wanting an on-site spa or fitness center, or travelers avoiding resort fees.
Choose La Siesta if you want oceanfront cottages with full kitchens, a heated pool, and water taxi to sister resorts. Skip it if you want an on-site spa or fitness center, or balk at the $65/day cashless resort fee.
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Before You Book
The details that matter after you've narrowed down your options.
Best for
- Families wanting oceanfront cottages and villas with full kitchens, heated pool, on-site dining, and water taxi to sister resorts
- Couples seeking Tulum-inspired oceanfront accommodations with poolside dining and sunset views
- Boaters wanting transient marina slips with water taxi access to Three Waters' larger marina facilities
- Pet owners wanting a beachfront resort that welcomes dogs with no weight limit
Not ideal for
- Guests wanting an on-site spa or fitness center — available at sister resorts Amara Cay and Three Waters via water taxi
- Budget-conscious travelers — the $65/day resort fee adds significantly to quoted room rates
- Guests who prefer cash — all Islamorada Resort Collection properties are cashless
Quick facts
| Address | 80241 Overseas Highway, Islamorada, FL 33036 |
|---|---|
| Phone | (305) 433-9942 |
| Check-in / Out | 4:00 PM / 11:00 AM |
| Parking | On-site (complimentary, included in resort fee) |
| Pets | Yes (fee may apply) |
| Beach access | Yes |
| Pool(s) | Yes |
| Spa | No |
| EV charging | No |
Location & nearby
La Siesta Resort & Villas is located in Upper Matecumbe Key within Islamorada.
What's nearby
- Theater of the Sea(1.5 mi, 30 min walk)
- Robbie's Marina (Tarpon Feeding)(5 mi, 100 min walk)
- Windley Key Fossil Reef Geological State Park(2 mi, 40 min walk)
- Islamorada Fish Company(2 mi, 40 min walk)
- Founders Park(2.5 mi, 50 min walk)
- Islamorada Brewery & Distillery(3.5 mi, 70 min walk)
- History of Diving Museum(2.5 mi, 50 min walk)
- Hurricane Monument(0.8 mi, 16 min walk)
Amenities overview
Property highlight features
- Tulum-inspired oceanfront cottages, villas with Villa Butler, and oceanfront casitas
- On-site dining: SIDECAR poolside bar, Siesta Mercato, ReelCatch, and Tiki Bar
- Heated zero-entry pool plus access to five pools across the Islamorada Resort Collection
- Marina with transient slips for boats up to 30 feet
- Private beach with walk-in waters and marina views
- Complimentary Rum Runner water taxi to Amara Cay and Three Waters resorts
- Complimentary kayaks, paddleboards, bicycles, and local shuttle (MM 77–85)
- Pet-friendly across all room types ($50/pet/day, no weight limit)
- Florida Green Lodging certified
Pricing positioning
Typical nightly pricing tends to fall in the $$$ range, depending on season and room type.
oceanfront resort with on-site dining, marina, and cross-resort access via Islamorada Resort Collection
Compare current room availability and secure member-only pricing.
We handle our lodging checks through Expedia's network engine so you can lock in hidden seasonal discounts and stack your One Key™ rewards points across different island brands.
Independent Decision Engine
Florida Keys Resorts operates as a fully objective, crowdsourced review system. We do not accept paid placements from hotels to alter their scoring records. Instead, we use standardized API connections to provide transparent third-party rate checks for our community.
How La Siesta Resort & Villas Compares to Other Islamorada Resorts
La Siesta Resort & Villas vs Islander Resort
- La Siesta Resort & Villas wins:Islamorada Resort Collection member with on-site dining, marina, water taxi, and Tulum-inspired oceanfront cottages
- Islander Resort wins:24-acre beachfront resort with bungalows, four dining venues, seaside sports, and ocean excursions
La Siesta Resort & Villas vs Amara Cay Resort
- La Siesta Resort & Villas wins:sister resort with Tulum-inspired cottages, on-site dining, marina slips, and pet-friendly beachfront
- Amara Cay Resort wins:contemporary hotel with live music, complimentary breakfast, and social poolside energy
La Siesta Resort & Villas vs Pines & Palms Resort
- La Siesta Resort & Villas wins:Islamorada Resort Collection member with four dining venues, marina, water taxi, and complimentary water sports
- Pines & Palms Resort wins:intimate 5-acre oceanfront tropical village with tiki bar, live music, boat charters, and 1930s Keys heritage
FAQs
Is La Siesta part of the Islamorada Resort Collection?
Yes. La Siesta Resort & Villas is one of three resorts in the Islamorada Resort Collection alongside Amara Cay Resort and Three Waters Resort & Marina. Guests can access all three properties via the complimentary Rum Runner water taxi, sharing five pools, twelve culinary destinations, fitness centers, and a PADI dive center across the collection.
What types of accommodations does La Siesta offer?
La Siesta offers Tulum-inspired oceanfront cottages with modern interiors and beachside patios, villas with full kitchens and Villa Butler service, oceanfront casitas with king beds and sleeper sofas, and accessible rooms. Villas include private yards and full kitchens for self-catering.
Does La Siesta have restaurants?
Yes. La Siesta has four on-site dining venues: SIDECAR poolside bar, Siesta Mercato (lobby market for grab-and-go), ReelCatch (Keys-inspired breakfast and dinner), and a Tiki Bar (lunch and dinner). Through the resort collection, guests also have access to twelve total culinary destinations across all three resorts.
Does La Siesta have a marina?
Yes. La Siesta has transient marina slips for boats up to 30 feet at $100/night ($150 over holidays, plus 7.5% tax). Additional marina services are available at sister resort Three Waters Resort & Marina via the complimentary water taxi.
Is La Siesta pet-friendly?
Yes. La Siesta welcomes pets with a $50 nonrefundable fee per pet per day, a maximum of two pets per room, and no weight limit. Pets must be leashed in public areas and are not permitted in pools or restaurants.
What does the $65 resort fee include?
The $65/day resort fee covers access to all three Islamorada Resort Collection resorts, five pools, fitness centers at Amara Cay and Three Waters, Rum Runner water taxi, local shuttle service (MM 77–85), daily bicycle and kayak/paddleboard rentals, enhanced WiFi, lobby coffee (7:30–11 AM), a reusable water bottle, self-parking, and beach/pool chaise lounges and umbrellas.
Does La Siesta have a pool?
Yes. La Siesta has a heated zero-entry pool open year-round (7 AM to sunset). Through the Islamorada Resort Collection, guests also have access to five total pools across the three resorts.
Do you need a car at La Siesta?
Not necessarily. The resort fee includes a complimentary local shuttle service between Mile Marker 77 and 85, covering most of Islamorada's restaurant and attraction corridor. The Rum Runner water taxi connects to sister resorts. Free on-site parking is available for guests with cars.