
Vacation rentals with a pool in Vaca Key
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Top-rated rentals with a pool in Vaca Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Beach House, Private Pool, Dock, Gulf View Sunsets
You don’t come to the islands to stay in a town—you come to slow down. Welcome to our tropical keys beach home, tucked away from the traffic and noise of US Hwy #1. Sway with the palms on the wraparound deck, soak in wide-open panoramic bay views, and catch fiery sunsets right off your dock. Fire up the BBQ, brew a Keurig, float in the private pool, or cast a line from the 300’ private pier/dock. Easy going island living with ocean / gulf breezes, comfy beds, quality linens, Wi-Fi, and cable TV.

Waterfront House with 37 ft Dock & Cabana Club
Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

Slip, Private Ramp, Pool, Trailer Parking, Freezer
7 DAY MINIMUM BOOKINGS / MAX 4 PERSONS NAUTI HIDEAWAY - This Nauti Stays Vacation Rental property is a 2-bedroom, 2-bath 2nd level 925 sq ft. condo located in Coco Plum, Marathon. Set in a well-protected, deep canal on the Atlantic, comes with a deep slip (length up to 40 ft) next to pool allowing access to the Atlantic Ocean and Florida Bay. ONSITE boat ramp & trailer (36 ft max) parking! Enjoy a heated or chilled pool after a boat day! Dock has water, power hook ups & fish cleaning station.

Lagoona-Matata
A truly magical place "Lagoona-Matata" sits on the edge of Vaca Cut showcasing fabulous views of the Gulf. The outdoor area flows from the patio to the pool deck, private sandy beach, tidal pool and then to the pier dock. "Vaca Cut" is a fast-moving body of water from incoming to outgoing tides with fish of every kind moving through that makes fishing from the dock great entertainment. The continuous plethora of sea life in the lagoon makes this property an experience unlike any other.

P01 - New 3 bed, 3 bath with private pool
This beautiful new home offers 3 bedrooms, 3 baths and a comfortable open floorplan. Additionally, this property boasts and abundance of fabulous outdoor living space and is ideally located minutes from Coco Plum Beach. - Maximum Occupancy: 6 guests (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 3 vehicle max - 3 bedroom/3 bathroom

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

4BR 3B, Heated Pool & Spa, 60' Dock
Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 4 BEDROOM/3 BATH canal front home. Bring your boat to the 60' dock on a 200' wide canal just 10' away from the Ocean. Relax by the pool/spa area after a day of fishing. A pool heater is offered as an option for your convenience. Please inquire about water heater fee and operating instructions before booking. (VR Lic # PLR2020-00104)

Boater’s Paradise 3br/2.5ba Villa with Slip!
Spectacular PET FRIENDLY 3 bed/2.5 bath 1350sf villa in beautiful Coral Lagoon, complete with a 40 foot wet slip and all the amenities! Spread out and enjoy the spacious, clean interior with free high speed wifi. Step outside to your boat and enjoy all the Gulf and Atlantic have to offer - both easily accessible in minutes. Relax with a drink at the pool after a long day of fun in the sun.

Oceanview Rooftop Retreat 3BR 3BA in Marathon FL
Welcome to Rooftop Bliss – the ultimate family getaway in Marathon, FL! This spacious 3BR/3BA villa is perfect for making memories together, with a private rooftop deck, resort-style pool, and a safe, gated community. Close to beaches, fishing spots, and fun island attractions, it's your home away from home in the Florida Keys.

Marathon one-level home on the Marina - with slip!
***New Listing! Recently renovated with all new furnishings and appliances*** Beautiful oasis in the heart of the Florida Keys, Marathon is a fisherman's paradise. Coral Lagoon is the perfect destination for a relaxing family getaway and this home is all new with stylish interior and unbeatable location.

Your Key Colony Beach Paradise Awaits!
This property is a fully remodeled 1,444 sqft 2 Bedroom, 2 bathroom accommodation located in Key Colony Beach Fl. Water view home situated on canal, w/ a 30 feet private sea wall and screen patio. Plus access to the Cabana Club.
Popular amenities for Vaca Key rentals with a pool
House rentals with a pool

Waterfront Pool Home w/ Private Dock, Tiki Hut & B

Welcome to Paradise! Private Pool, SUPs, Kayak!

Entire private two family water front home.

*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

Beautiful Beachfront Home w/ Pool/Tiki/Dock

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

Private Pool! Luxury Paradise Pointe, Pet Friendly
Condo rentals with a pool

Amazing Ocean Front Views Key Colony Beach

Mad Mahi | Housekeeping + Waterfront + Marina View

Beachside Unit 33-Private Tropical Beach Plus Pool

Ocean Views Heated Pool King Suite Ocean Isle

*New* Turtles Pace-Private Beach

Peaceful, Newly Renovated Condo With Boat-slip.

Private Beach in Marathons Key Colony Beach

2-story condo w/ panoramic bay views and balconies
Other vacation rentals with a pool

Castillo Del Mar- Ocean access from your backyard

Florida Keys Wellness Gem Tranquility & Activity

Tropical Keys Retreat | Pool | Hot Tub | Cinema

Emerald Palms ~ Waterfront ~ Pool ~ Dock ~ Games

Waterfront Villa Bring Your Boat Cabana Club Beach

Casa Blue Flamingo

KCB Tiki Hut Oasis: 37.5' Dock + Cabana Club!

3Bed 2Bath~Kayaks~Cabana Club~Swim Spa~Fish Equip
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Theater of the Sea
- Key Largo Kampground And Marina
- Ernest F. Coe Visitor Center
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