Winters Vacations Rentals - Vacation Rentals in San Pedro Underwater Archaeological Preserve State Park

Dates

Price

Guests

More

When do you want to travel?

We search multiple sites to find you the best prices.

Compare Price with Other Partners

From US $1,872

         

10.0 (106 Reviews)

House

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $308

         

|

9.5 (4 Reviews)

House

Key Lime Cottage in the heart of Islamorada

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $446

         

|

8.8 (62 Reviews)

Condo

Topsider Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $701

         

10.0 (91 Reviews)

House

TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $7,615

         

1.0 (1 Review)

Villa

Beachfront Villa at Islamorada BY THE GLAMHOMES

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $141

         

8.8 (84 Reviews)

Resort

Matecumbe Resort

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $1,263

         

10.0 (87 Reviews)

House

Now booking late 2026 and 2027. Oceanfront - Heated Pool - Dock - Over 1 acre

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $1,283

         

|

New

House

Private Beach Private overwater dock Heated Pool Mahi Key

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $1,424

         

10.0 (76 Reviews)

House

Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $2,081

         

10.0 (57 Reviews)

House

Next available April 25th, 2026 - Stunning Oceanfront Estate - Private Pool

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $544

         

10.0 (53 Reviews)

House

ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $905

         

10.0 (48 Reviews)

House

Beach Dream House, relax and enjoy the clear waters of Islamorada FL

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $1,316

         

10.0 (19 Reviews)

House

Egret House @ Tarpon Point

• Air Conditioner
• Pool
• TV

• Florida
• Islamorada

View Availability

From US $456

         

10.0 (18 Reviews)

House

Islamorada retreat "Bungalow Blue" w/heated pool, Bikes, BBQ, amenities galore!

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $387

         

10.0 (15 Reviews)

Condo

Ocean View with protected dock on lagoon with private boat ramp

• Air Conditioner
• TV
• Security/Safety

• Florida
• Lower Matecumbe Key

View Availability

From US $1,059

         

10.0 (11 Reviews)

House

The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $758

         

10.0 (10 Reviews)

House

Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $385

         

10.0 (10 Reviews)

House

Tarpon Bend ocean view with boat lifts

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $1,115

         

10.0 (5 Reviews)

House

The Snook House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $670

         

10.0 (2 Reviews)

House

Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua

• Air Conditioner
• Parking
• Pool

• Florida
• Islamorada

View Availability

From US $2,530

         

10.0 (1 Review)

House

Private Beach/Private overwater dock/Heated Pool/Mahi Key

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $518

         

10.0 (1 Review)

Villa

Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

From US $418

         

10.0 (1 Review)

House

Paradise Retreat

• Air Conditioner
• Parking
• TV

• Florida
• Islamorada

View Availability

From US $700

         

9.8 (58 Reviews)

House

Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock

• Air Conditioner
• Parking
• Pet Friendly

• Florida
• Islamorada

View Availability

★ Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in San Pedro Underwater Archaeological Preserve State Park.