
Vacation rentals with a hot tub in Big Pine Key
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Top-rated hot tub rentals in Big Pine Key
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Cozy 2 br/2 bath home in Cudjoe
Discover a slice of Floridian paradise in our charming 2b/2bath located in Venture Out community, Cudjoe Key. Two bedrooms and an outdoor patio promise relaxation, while community amenities such as a pool, tennis courts, and kids' playground are available. A place to experience the laid-back Florida lifestyle and create unforgettable memories. Book your stay with us today and come live the dream in Cudjoe Key! ****Upon entry, there is a one-time community fee paid at the gate check-in: $125.

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Rise And Shine On The Water
Spectacular sunrise view! Room to park one vehicle & have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans., GRILL, TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

2Bd/1Ba Waterfront Retreat w/35’ Dock
Discover the FL Keys in this bright & beachy 2-queen bed, 1-bath waterfront home in Venture Out on Cudjoe Key. Enjoy your fresh catch in the full kitchen, laundry in-house, nice wide canal with 35’ dock for your boat just steps from your door. Indulge in unparalleled amenities & scenic beauty: oceanfront pool, hot tub, marina w/marine fuel, wash station, store; tennis, bball, pickle ball, & playground. $125 add’l resort fee paid direct to Venture Out at gate. Incl Bikes & kayaks for your use.

Island Paradise
*** Please note: There is a one time registration fee of $125 to be paid at gate*** Cozy keys getaway w/ ocean front heated pool, boat ramp and more. Relax in this 1 BR, 1 BA manufactured home in a resort style park with heated pool, hot tub, boat ramp, sports courts and walkable dining. This clean well kept home features a king bed in primary BR and queen gel memory foam pullout sofa in living room. Fully stocked kitchen! Hair dryer, shampoo, conditioner, bath soap, etc. are furnished.

Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Waterfront Sanctuary in the Keys!
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Spanish Queen @Venture Out
Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

Feb. Save $!$ Oceanfront 4 Bikes/2Kayaks. KING bed
*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Dock, Beach Club, Ocean & Gulf Access, Pickle Ball
Our place is a spacious half of a duplex (2050 sq ft), with Penthouse Suite. 37.5 foot dock, and immediate access to ocean and gulf. Across the street from 9-hole golf course and tennis courts. Enjoy the beach and a pool at the prestigious Cabana Club (access included). Walk in early evening to Sunset Park to watch a truly special sunset. Wifi, Cable, and Sports Package.
Popular amenities for Big Pine Key hot tub rentals
House rentals with a hot tub

Marathon Star - home with hot tub

Couples Getaway, Suites-Marlin Bay Resort & Marina

Secluded Waterfront home, Views, Dock, Amenities,

Ocean Front Home in Great Location

Waterfront with Boat Dock, Heated Pool, Amenities

Waterfront w/pool and hot tub

Waterfront 6BR Luxury Retreat w/ Pool & Dock

Palm Breezes! Room for Everyone on the Ocean.
Villa rentals with a hot tub

Florida Keys | 2BR Stay – No Hidden Fees

Seas the Keys Getaway with plunge pool/spa

Florida Keys 3BR w/ Perks – No Hidden Fees

Saltwater Social ~ Game Room ~ Pool ~ Dock ~ Views

Beachfront • Heated Pool • Hot Tub • Oceanview

Florida Keys 3BR 1Lvl Villa w/ No Hidden Fees

Canal/Dock - Cabana Club - Pickleball - Remodeled

FL Keys 2BR 2Lvl | Nr Spa+KidsClb | No Hidden Fees
Other vacation rentals with a hot tub

Waterfront with Boat Lift/Kayaks and Hot Tub

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Cudjoe Key Home with a View

Newly Renovated 2/2 Bath Condo, with shared pool

Luxury Waterfront Retreat with Dockage & Pool

Gorgeous 4-bedroom home with 8-person hot tub

Waterfront 2-bedroom Home w/Pool and Spa

Vacation Home Heron Hideaway
Quick stats about vacation rentals with a hot tub in Big Pine Key

Total vacation rentals
Explore 10 vacation rentals in Big Pine Key

Nightly prices starting at
Big Pine Key vacation rentals start at G$22,996 GYD per night before taxes and fees

Verified guest reviews
Over 40 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Big Pine Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Big Pine Key rentals

5 Average rating
Big Pine Key stays are highly rated by guests—averaging 5 out of 5!
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- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- Long Beach
- Conch Key
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Ernest Hemingway Home & Museum
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Southernmost Point
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Boyd's Key West Campground
- Key West Butterfly & Nature Conservatory
- History Of Diving Museum
- Key West Lighthouse Museum




