Holiday 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.

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Top guest favourite

Home in Marathon

4.99 out of 5 average rating, 139 reviews

Cancellation Deal: 08/02 thru 08/09

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Top guest favourite

Townhouse in Marathon

4.97 out of 5 average rating, 176 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also, our marina is 100% open and operational should you need to rent a slip during your stay Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house

Top guest favourite

Apartment in Marathon

5 out of 5 average rating, 21 reviews

*NEW* Private Beach, pool & fully loaded kitchen

Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

Top guest favourite

Home in Marathon

5 out of 5 average rating, 12 reviews

Sunshine & Serenity on Waterfront, Tiki/50ft dock!

Discover Mariner’s Muse, an enchanting waterfront retreat on a spacious fully fenced lot in serene Coco Plum Beach. Accommodating up to 6 guests, this sanctuary offers breathtaking water views from every room, a private balcony terrace and tiki hut, ideal for sipping coffee at sunrise or enjoying cocktails at sunset. Dive into relaxation in the expansive 12,200 SF yard featuring an oversized pool w/ optional heating and cooling. Experience the ultimate getaway with full access to this paradise!

Top guest favourite

Apartment in Marathon

4.96 out of 5 average rating, 105 reviews

Slip, Ramp, Pool, Trailer Parking, Bait 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.

Guest favourite

Townhouse in Marathon

4.96 out of 5 average rating, 145 reviews

Boater’s Paradise 3br/2.5ba at Coral Lagoon

*PLEASE NOTE* Villa slips/canal are under construction until Fall 2025. Please inquire before booking. 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.

Top guest favourite

Home in Marathon

5 out of 5 average rating, 11 reviews

Ocean Views Galore- Bring Boat- Built New 2024

Immerse into the finest Marathon Key has to offer.. Escape to the long ocean views, endless ocean sounds and breeze in this Brand New Built in 2024 Stunning Water Front Home. With Amities galore. Heated/ Chilled Pool/Spa/ Kayaks, Paddle Boards, Bicycles, Boat Dock, Games, Perfect Location, Walk or Bike to all. Fisherman's paradise. Instant Ocean or Gulf Access. One of 3 homes on this one-acre private ocean gulf lot that has the look and feel of a private island with 400 feet of bulk head

Top guest favourite

Home in Key Colony Beach

4.95 out of 5 average rating, 119 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Superhost

Villa in Marathon

4.9 out of 5 average rating, 337 reviews

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!

Superhost

Home in Marathon

4.94 out of 5 average rating, 62 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Guest favourite

Home in Marathon

5 out of 5 average rating, 7 reviews

Chiquita Waterfront Canal Home

Kick back, unplug, and chum up some yellowtail at one of the best locations in the middle keys! Casa Chiquita is a recently updated ground level pool home tucked away on the closest gulf side canal to the Vaca Cut in Marathon, FL. The property is directly across the street from the Gulf of America and has 75 feet of dockage. You’ll have a nice protected space for a boat or two and can be on the reef with a rod in your hand in minutes.

Guest favourite

Home in Marathon

4.98 out of 5 average rating, 95 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

Enjoy breathtaking views of the Gulf and Ocean from the screened in patio of this beautiful 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)