Resort holiday rentals in Estero Island

Hyatt Coconut Cove - Xmas (Dec 20-27 2026) Studio

Celebrate an unforgettable Christmas (Dec 20–27, 2026) in this luxury studio at Hyatt Coconut Cove. Sleeping four with a king bed and sofa bed, this refined sanctuary is perfect for a festive escape. Trade the winter frost for the soft glow of holiday lights over Estero Bay. Drift down the 1,000-foot lazy river or take the private boat shuttle to a secluded beach. Every detail is designed for holiday relaxation. Book early to secure this premium Christmas week getaway before it's gone!

Beachfront w/Balcony Pool 1bdrm Dwtn FtMyers Beach

Ocean/Pool view Diamondhead Beach Resort Ft Myers Beach 1 bedroom, Living room w pullout sofa, kitchenette furnished NEW POOL, towels provided Beach front,beach chairs, umbrella, volleyball court, workout room, free parking Great restaurant & bar indoors Grocery store less then a mile away. Downtown less than 1/2 mile, easy walking distance with shopping and restaurants. 10th floor overlooking pool & Gulf of Mexico. Great beach access. Fitness Center diamondheadfl website info on property

Beachfront Lani Kai Island Resort - Standard King

For nearly four decades, the Lani Kai Island Resort has welcomed guests from all over the world. The Conidaris Family has developed the Lani Kai Island Resort on Fort Myers Beach into the amazing and iconic property it is today. From the beginning, the hotel was the passion project of Bob & Grace Conidaris who wanted to create a fun, energetic place for both guests and the community.

Superior King | Lazy River, Tennis & Beach Shuttle

Ignite your getaway as we cruise from our marina to the Gulf, kayak mangroves, and lounge by five heated pools with lazy-river bliss. Just minutes from Downtown Naples, 5th Avenue shopping, white sands, and vibrant dining—so every day brings new water, wellness, and city adventures at your doorstep.

Charter Resort Of Naples Bay - 2 Bedroom

Waterfront Elegance w/ Gulf-Access & Boat Marina – Naples, FL Wake to gentle bay breezes on your screened lanai, have breakfast in your full kitchen, then kayak, swim, or dock your boat. In the evening, dine lakeside as the sunset paints the Gulf horizon.

Beachfront and Outdoor Pool | Pets Welcome Here!

Discover serene beach bliss & vibrant nightlife steps away! We offer unforgettable sunset views along with pool parties and live entertainment. Perfect for groups of friends, family or couples craving relaxation at this sandy beachfront resort.

4737 Jackfish St - 4 Bedroom W Den

Luxury Waterfront with Heated Pool & Gulf Access – Bonita Springs, FL Wake to Estero Bay views, sip coffee by the heated pool, explore Coconut Point shops, launch kayaks or bikes, and end the day with breathtaking waterfront sunsets.

Enjoy 5 Star Luxury at the Naples Bay Resort

The Naples Bay Resort helps make your vacation perfect. The Tuscan-style resort has all the amenities you would expect in your beach destination vacation. Located in the perfect location next to the bay in the heart of Old Naples.

Hideaway Waterfront Resort Suite A3

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

Hideaway Waterfront Resort GR A4

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

Hideaway Waterfront Resort Guest Suite A18

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

Hideaway Waterfront Resort GS(2) A37

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue.