Upper Keys Wedding Properties

Let Freewheeler Vacation Rentals help you find the perfect location for your Florida Keys wedding. We have numerous spectacular locations to fit every wedding style & size. We can also set you up with the best wedding planners, caterers and officiants in town. Take a look below at some of our featured wedding properties.

The following properties are perfect for smaller intimate weddings:

Markeysa

Location: Islamorada
Bedrooms: 4 Bathrooms: 4 Bedding: King, Queen, Queen, 2 Twins, Sleeper Sofa
Description: Absolutely gorgeous ocean front home (French Caribbean inspired architecture) located in Lower Matecumbe. The main house consists of three bedrooms and three baths plus a study. The beachfront guest house is a one bedroom, one bath cottage right on the beach! There is a saltwater pond full of sea life in between the beach cottage and the pool! Mile Marker 75.7, Oceanside. Wedding size: 25 people max
Rates/FeesRental: $6,500.00 /weekly To $7,000.00 /weekly

113 Sunset

Location: Islamorada
Bedrooms: 4 Bathrooms: 3 Bedding: 2 Kings, 2 Queen, 2 Twins
Description: Come and stay in this adorable beach front home located on the crystal clear Atlantic Ocean! The home has plenty of room for your whole family to relax! Grab a cool drink and a book and relax in the Hammock while listening to the serene ocean! What more could you want in a vacation?
Rates/Fees Rental: $3,000.00 /weekly To $3,500.00 /weekly

114 Plantation

Location: Islamorada
Bedrooms: 2 Bathrooms: 2 Bedding: King, 2 Trundle, Futon
Description: Conch style home, on large wooded lot directly on Florida Bay. Bedrooms on the top floor with inside staircase. Protected deep water dockage, easy access to the ocean via Tavernier or Snake Creeks, great swimming basin, large backyard, gated and very private! Located Mile Marker 88, Bayside.
Rates/Fees Rental: $1,800.00 /weekly To $1,980.00 /weekly

76004 Caylors

Location: Islamorada
Bedrooms: 4 Bathrooms: 3 Bedding: King, Queen, 2 Twins, Double, Sleeper Sofa
Description: Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Mile Marker 76, Bayside.
Rates/Fees Rental: $2,500.00 /weekly To $2,750.00 /weekly

50 Schooner Bay

Location: Islamorada
Bedrooms: 4 Bathrooms: 3 Bedding: King, 2 Queens, 2 Twins
Description: Aguazul is located at Mile Marker 88, in beautiful Islamorada. This gorgeous four bedroom/three bath home will sleep 8 people very comfortably. Aguazul has everything you could want for a perfect vacation home. Heated oceanfront pool, dockage, fishing right from the 300 ft pier, a kitchen on both the ground and second floor, flat screen TV, wireless Internet and a sunrise and ocean view that are priceless. Let Aguazul be your next Keys vacation home, it will be one you will not soon forget.
Rates/Fees Rental: $5,500.00 /weekly To $6,500.00 /weekly

The following properties are perfect for larger weddings:

Little Bay

Location: Islamorada
Bedrooms: 6 Bathrooms: 6 Bedding: King, 2 Queens, 4 Twins, 3 Murphy Beds, 3 S/S
Description: Beautifully landscaped private one acre gated compound on the bayside with three separate rentals; Upper/Lower Duplex, each 1,500 sq ft w/2 BR (MBR-queen/twin, 2nd BR- 2 twins), 2 baths, full kitchen, laundry, family room w/ sofabed - sleeps 6 total. Each w/ 10' x 40' porch overlooking bay. Cottage: 1,300 sq ft w/ huge master BR (King and sofabed), 2 bath, laundry room, family room, kitchen, sun room combined (w/ couch and sofabed), sleeps 6 total. Large private boat basin with Chickee Hut, Pergola, bait prep station and fresh water shower on dock. Located in the heart of Islamorada...within walking distance to activities, shopping, marinas, restaurants, grocery stores, etc. Duplex (each) $2400/wk, Cottage $2400/wk. (Rates may vary depending on the season). A full set of photos are available! Mile Marker 82.2, Bayside. The back yard can accommodate 60’-80’ tent. A discount is offered when renting all three + a wedding surcharge for cleanup.
Rates/Fees Rental: $2,000.00 /weekly To $2,400.00 /weekly

83003 Overseas Hwy

Location: Islamorada
Bedrooms: 4 Bathrooms: 3 Bedding: 2 King, 2 Queen, 2 Sofa Sleepers
Description: If you are looking for the perfect destination vacation this is it! There are 2 homes with 2 bedrooms each on this one of a kind ocean front property. Have a lazy day by the pool or soak up the sun on the beach. Looking for the perfect setting for your wedding ... well look no more, this is it! Both homes have a beautiful view of the ocean, and perfectly landscaped yard. Keep everyone in the family happy with the great game room complete with wet bar, pool table and poker table.
Rates/Fees Rental: $7,000.00 /weekly To $10,000.00 /weekly

The Reef House

Location: Islamorada
Bedrooms: 4 Bathrooms: 3 Bedding: King, 2 Queens, 2 Twins, Sofa Sleeper
Description: New Oceanfront Home with large open living room. Spectacular views, putting green, pool and shallow water dockage. Next door to quaint resort with deep dockage, restaurant, bar and water-sports. Within walking distance to Holiday Isle Resort. Can be combined with a 3 bedroom/2 bath cottage. Excellent for family reunions, corporate retreats, weddings, or multiple families. Mile Marker 84.6, Oceanside.
Rates/Fees Rental: $6,000.00 /weekly To $6,500.00 /weekly

Alligator Reef

Location: Islamorada
Bedrooms: 3 Bathrooms: 2 Bedding: King, Queen, 2 Twins, Sofa Sleeper
Description: Brand new homes right on the ocean. Beautiful views, ocean breezes, your own private pool. Private deck on house to enjoy the trade winds and sip your margaritas. Dockage available. Pets ok. Your own private paradise, who could ask for more? Mile Marker 84.7, Oceanside.
Rates/Fees Rental: $4,900.00 /weekly To $5,390.00 /weekly

La Playa

Location: Islamorada
Bedrooms: 7 Bathrooms: 5 Bedding: King, 2 Queen, 4 Twins, 2 Sofa Sleepers
Description: MM 76.5 Beautiful home perfect for weddings, family reunions or just the perfect backdrop for the ideal vacation. Extremely private home situated on 8 acres of land with a beautiful sandy beach, pool, Jacuzzi, dockage and fishing pier... Is there any more that you can ask for? How about a guest house? Main house sleeps 6-8 with 4 bedrooms 3 bath. Guest House with three bedrooms, accommodates up to 8. Event Fee $2750.00 for all large weddings and functions
Rates/Fees Rental: $10,000.00 /weekly

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